The 20 greatest hip-hop tours of all time Our ranking, inspired by all the great rap acts on the road this summer, is 100% correct

Look around and it might feel like we’re in a golden age of rap tours.

Rhyme greats De La Soul recently finished a European tour billed The Gods of Rap with the legendary Public Enemy, Wu-Tang Clan and Gang Starr’s DJ Premier. And the summer concert season is set to feature even more high-profile hip-hop shows.

West Coast giant Snoop Dogg is headlining the Masters of Ceremony tour with such heavyweights as 50 Cent, DMX, Ludacris and The Lox. Lil Wayne is doing a string of solo gigs and will launch a 38-city tour with pop punk heroes blink-182 starting June 27. Stoner rap fave Wiz Khalifa will headline a 29-city trek on July 9. The reunited Wu-Tang Clan continue their well-received 36 Chambers 25th Anniversary Celebration Tour, and Cardi B will be barnstorming through the beginning of August.

With all this rap talent on the road, The Undefeated decided to take a crack at ranking the 20 greatest hip-hop tours of all time.

Our list was compiled using several rules: First and foremost, the headliners for every tour must be from the hip-hop/rap genre. That means huge record-breaking, co-headlining live runs such as Beyoncé and Jay-Z’s On the Run II Tour were not included, given Queen Bey’s rhythm and blues/pop leanings. We also took into account the cultural and historical impact of each tour. Several artists, ranging from Run-DMC and Salt-N-Pepa to MC Hammer and Nicki Minaj, were included because they broke new ground, beyond how much their tours grossed. For years, hip-hop has battled the perception that it doesn’t translate well to live performance. This list challenges such myopic ideas.

With only 20 spots, some of rap’s most storied live gigs had to be left off the list. Many were casualties of overlap, such as Run-DMC and the Beastie Boys’ memorable 1987 Together Forever Tour and the Sizzling Summer Tour ’90, which featured Public Enemy, Heavy D & the Boyz, Kid ’n Play, Digital Underground and Queen Latifah. The 12-date Lyricist Lounge Tour, a 1998 showcase that featured Big Punisher, The Roots, De La Soul, Black Star, Common, Black Moon’s Buckshot and Fat Joe, also just missed the cut.

You may notice that Tupac Shakur and The Notorious B.I.G. are missing from the list. But this was no momentary lapse of sanity. ’Pac’s and Biggie’s brief runs took place when rap shows were beginning to become a rarity, leaving most of their memorable stage moments to one-off shows. Dirty South royalty Outkast’s strongest live outing, when Big Boi and Andre 3000 reunited in 2014, was not included because it was less of a tour and more of a savvy festival run.

There are other honorable mentions: Def Jam Survival of the Illest Tour (1998), which featured DMX, the Def Squad, Foxy Brown, Onyx and Cormega; the Ruff Ryders/Cash Money Tour (2000); Anger Management 3 Tour with Eminem and 50 Cent (2005); J. Cole’s Dollar & A Dream Tour (2013); and Drake’s Aubrey & The Three Migos LIVE! tour (2018).

With that said, on with the show!

20. Pinkprint Tour (2015)

Nicki Minaj, featuring Meek Mill, Rae Sremmurd, Tinashe and Dej Loaf

The most lucrative hip-hop trek headlined by a woman also served as the coronation of Nicki Minaj as hip-hop’s newest queen. What made The Pinkprint Tour such a gloriously over-the-top affair was its seamless balance of dramatic Broadway-like theater, silly high jinks and a flex of artistic ferocity. One moment Minaj was in a black lace dress covering her eyes while mourning the loss of a turbulent union during “The Crying Game.” The next, she was backing up her memorable appearance on Kanye West’s “Monster” as the most wig-snatching guest verse of that decade. And the Barbz went wild.

Gross: $22 million from 38 shows

Kendrick Lamar performs during the Festival d’ete de Quebec on Friday, July 7, 2017, in Quebec City, Canada.

Amy Harris/Invision/AP

19. The Damn. Tour (2017-18)

Kendrick Lamar, featuring Travis Scott, DRAM and YG

When you have dropped two of the most critically lauded albums of your era in Good Kid, M.A.A.D City (2012) and To Pimp a Butterfly (2015), there’s already an embarrassment of riches to pull from for any live setting. But Kendrick Lamar understood that to live up to his bold “greatest rapper alive” proclamation he also needed populist anthems to turn on the masses. The Damn. album and world tour presented just that, as he led his followers each night in an elevating rap-along. It kicked off with a martial arts film, a cheeky nod to Lamar’s Kung Fu Kenny alter ego, before launching into the chest-beating “DNA.”

Gross: More than $62.7 million from 62 shows

Drake and Future performing on stage during The Summer Sixteen Tour at AmericanAirlines Arena on Aug. 30, 2016 in Miami.

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18. Summer Sixteen Tour (2016)

Drake and Future

This mammoth, co-headlining tour was a no-brainer: Drake, the hit-making heartthrob, Canada’s clap-back native son and part-time goofy Toronto Raptors superfan. And Future, the self-anointed Atlanta Trap King, gleeful nihilist and producer, whose slapping, codeine-addled bars made him a controversial figure on and off record. The magic of this yin/yang pairing shined brightest when they teamed up to perform such tracks as “Jumpman” and “Big Rings” off their industry-shaking 2015 mixtape What a Time to Be Alive. When the smoke settled, Drake and Future walked away with the highest-earning hip-hop tour of all time.

Gross: $84.3 million from 54 shows

From left to right, Sandra ‘Pepa’ Denton, DJ Spinderella and Cheryl ‘Salt’ James perform on stage.

17. Salt-N-Pepa Tour (1988)

Featuring Keith Sweat, Heavy D & the Boyz, EU, Johnny Kemp, Full Force, Kid ’n Play and Rob Base

It may seem preposterous in this outspoken, girl-power age of Cardi B, Lizzo, Megan Thee Stallion, Kash Doll, Young M.A, Tierra Whack and City Girls, but back in the early ’80s, the thought of a “female” rhyme group anchoring a massive tour seemed out of reach. That was before the 1986 debut of Salt-N-Pepa, the pioneering group who’s racked up a plethora of groundbreaking moments and sold more than 15 million albums. The first female rap act to go platinum (Hot, Cool & Vicious) and score a Top 20 hit on the Billboard 200 (“Push It”), Salt-N-Pepa led a diverse, arena-hopping showcase that gave the middle finger to any misogynistic notions. And Salt, Pepa and DJ Spinderella continue to be road warriors. They’re currently on New Kids on the Block’s arena-packing Mixtape Tour.

Encore: Opening-act standouts Heavy D & the Boyz would co-headline their own tour the following year off the platinum success of their 1989 masterpiece Big Tyme.

16. Glow in the Dark Tour (2008)

Kanye West, featuring Rihanna, N.E.R.D, Nas, Lupe Fiasco and Santigold

Yes, Kanye West has had more ambitious showings (2013-14’s button-pushing Yeezus Tour) and more aesthetically adventurous gigs (the 2016 Saint Pablo Tour featured a floating stage, which hovered above the audience). But never has the Chicago-born visionary sounded so hungry, focused and optimistic than he did on his first big solo excursion, the Glow in the Dark Tour.

Before the Kardashian reality-show level freak-outs and MAGA hat obsessing, West was just a kid who wanted to share his spacey sci-fi dreamscape with the public, complete with a talking computerized spaceship named Jane. Even the rotating opening acts — topped off by the coolest pop star on the planet, Rihanna — were ridiculously talented.

Gross: $30.8 million from 49 shows

15. I Am Music Tour (2008-09)

Lil Wayne, featuring T-Pain and Keyshia Cole

Between 2002 and 2007, Young Money general Lil Wayne was hip-hop’s hardest-working force of nature, releasing an astounding 16 mixtapes. Then Weezy broke from the pack with the massively successful I Am Music Tour. The bulk of Lil Wayne’s 90-minute set was propelled by his career-defining 2008 album Tha Carter III, which by the show’s second leg had already sold 2 million copies. By the time T-Pain joined the New Orleans spitter for a playful battle of the featured acts, Lil Wayne’s takeover was complete.

Gross: $42 million from 78 shows

MC Hammer, performing on stage in 1990, had a large entourage for his Hammer Don’t Hurt ’Em Tour.

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14. Hammer Don’t Hurt ’Em Tour (1990-91)

MC Hammer, featuring En Vogue and Vanilla Ice

With 15 background dancers, 12 singers, seven musicians, two DJs, eight security men, three valets and a private Boeing 727 plane, MC Hammer’s world tour was eye-popping. Rap fans had never seen anything of the magnitude of the Hammer Don’t Hurt ’Em stadium gigs, which recalled Parliament-Funkadelic’s army-size traveling heyday in the 1970s.

Each night the Oakland, California, dancing machine, born Stanley Burrell, left pools of sweat onstage as if he was the second coming of James Brown. If the sight of more than 30 folks onstage doing the Running Man, with MC Hammer breaking into his signature typewriter dance during “U Can’t Touch This,” didn’t make you get up, you should have checked your pulse.

Gross: $26.3 million from 138 shows

13. Things Fall Apart! Tour (1999)

The Roots

Each gig was a revelation. This was no surprise given that Philadelphia hip-hop collective The Roots, formed by longtime friends drummer Questlove and lead lyricist Black Thought, had a reputation for being unpredictable. Still, it’s ironic that a group known for being the ultimate road warriors — they were known for touring 45 weeks a year before becoming the house band on The Tonight Show Starring Jimmy Fallon in 2014 — is represented on this list by one of their shortest tours.

But the brilliant Things Fall Apart club and hall sprint, which took place throughout March 1999, proved to be an epic blitz fueled by the band’s most commercially lauded material to date, Questlove’s steady percussive heart and the inhuman breath control of Black Thought.

Encore: Neo soul diva Jill Scott, who co-wrote The Roots’ breakout single “You Got Me,” gave fans an early taste of her artistry as she joined the band onstage for some serious vocal workouts.

12. House of Blues’ Smokin’ Grooves Tour (1996)

The Fugees, Cypress Hill, A Tribe Called Quest, Busta Rhymes, Ziggy Marley and Spearhead

While gangsta rap was topping the charts, the hip-hop industry faced a bleak situation on the touring front. Concert promoters were scared to book “urban” acts in large venues. Enter the House of Blues’ Kevin Morrow and Cara Lewis, the booking agent who achieved mythic status when she received a shout-out on Eric B. & Rakim’s 1987 anthem “Paid in Full.” The pair envisioned a Lollapalooza-like tour heavy on hip-hop and good vibes. The first ’96 incarnation came out of the gate with Haitian-American rap trio The Fugees, multiplatinum weed ambassadors Cypress Hill, A Tribe Called Quest and Busta Rhymes.

Encore: The series, which has also featured Outkast, The Roots, Lauryn Hill, Gang Starr, The Pharcyde, Foxy Brown and Public Enemy, is credited with opening the door for a return to more straight-ahead hip-hop tours led by Jay-Z, DMX and Dr. Dre.

Kanye West (left) and Jay-Z (right) perform in concert during the Watch The Throne Tour, Sunday, Nov. 6, 2011, in East Rutherford, N.J.

AP Photo

11. Watch the Throne Tour (2011-12)

Jay-Z and Kanye West

In better times, Jay-Z and Kanye West exhibited lofty friendship goals we could all aspire to, with their bromance popping on the platinum album Watch the Throne. Before their much-publicized fallout, Jay-Z and West took their act on the road for the mother of all double-bill spectacles.

Two of hip-hop’s greatest traded classics such as the ominous “Where I’m From” (Jay-Z) and soaring “Jesus Walks” (West) from separate stages on opposite sides of the venue. Those lucky enough to catch the tour can still recall the dream tag team launching into their encore of “N—as in Paris” amid roars from thousands of revelers.

Gross: $75.6 million from 63 shows

10. The Miseducation Tour (1999)

Lauryn Hill, featuring Outkast

In 1998, Lauryn Hill wasn’t just the best woman emcee or the best emcee alive and kicking. The former standout Fugees member was briefly the voice of her generation as she rode the multiplatinum, multi-Grammy success of her solo debut The Miseducation of Lauryn Hill. By February 1999, it was time to take the show on the road. Hill and her 10-piece band went beyond the hype, especially when they tore through a blistering take of the heartbreaking “Ex-Factor.”

Encore: Outkast (Atlantans Andre 3000 and Big Boi) rocked the house backed by some conspicuous props, including two front grilles of a Cadillac and a throwback Ford truck, kicked off their own headlining Stanklove theater tour in early 2001.

9. No Way Out Tour (1997-98)

Sean “Puff Daddy” Combs, Lil’ Kim, Ma$e, Busta Rhymes, Foxy Brown, 112, The Lox, Usher, Kid Capri, Lil’ Cease and Jay-Z

The Los Angeles Times headline spoke volumes: “Combs to Headline Rare Rap Tour.” Combs, of course, is Sean “Diddy” Combs, the music, fashion, television and liquor mogul who Forbes estimates now has a net worth of $820 million. But back then, the hustler formerly known as Puff Daddy was struggling to keep his Bad Boy Records afloat after the March 9, 1997, murder of Brooklyn, New York, rhyme king The Notorious B.I.G.

But out of unspeakable tragedy rose Combs’ chart-dominating No Way Out album and an emotional all-star tour. Despite suggestions that large-scale rap shows were too much of a financial gamble, Puffy rallied the Bad Boy troops and a few close friends and proved the naysayers wrong. The No Way Out Tour was both a cathartic exercise and a joyous celebration of life. “It’s All About the Benjamins” shook the foundation of every building as Combs, The Lox and a show-stealing Lil’ Kim made monetary excess look regal. And the heartfelt Biggie tribute “I’ll Be Missing You,” which was performed live at the 1997 MTV Video Music Awards, had audiences in tears.

Gross: $16 million

Rap stars, from left, Redman, foreground, DMX, Method Man and Jay-Z join host DJ Clue, background left, in a photo session on Jan. 26, 1999, in New York, after announcing their 40-city Hard Knock Life Tour beginning Feb. 27, in Charlotte, N.C.

AP Photo/Kathy Willens

8. Hard Knock Life Tour (1999)

Jay-Z, featuring DMX, Redman and Method Man

Jay-Z stands now as hip-hop’s most bankable live draw. In 2017, the newly minted billionaire’s 4:44 Live Nation production pulled in $44.7 million, becoming America’s all-time highest-grossing solo rap jaunt. It’s a long way from the days of Jay-Z lumbering through performances in a bulletproof vest when he was last off the bench on Puff Daddy’s No Way Out Tour.

Surely the seeds of Jay-Z’s evolution as a concert staple were first planted on his Hard Knock Life Tour, which was documented in the 2000 film Backstage. This was a confident, full-throated Shawn Carter, and he would need every ounce of charisma, with Ruff Ryders lead dog DMX enrapturing fans as if he were a Baptist preacher at a tent revival and the duo of Redman and Method Man rapping and swinging over crowds from ropes attached to moving cranes. What a gig.

Gross: $18 million

Flavor Flav (left) and Chuck D (right) of the rap group Public Enemy perform onstage in New York in August 1988.

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7. Bring the Noise Tour (1988)

Public Enemy and Ice-T, featuring Eazy-E & N.W.A. and EPMD

There has always been a controlled chaos to a Public Enemy live show. Lead orator Chuck D jolted the crowd with a ferocity over the intricate, combustible production of the Bomb Squad while clock-rocking Flavor Flav, the prototypical hype man, jumped and zigzagged across the stage.

DJ Terminator X cut records like a cyborg and never smiled. And Professor Griff and the S1Ws exuded an intimidating, paramilitary presence. Armed with their 1988 watershed black nationalist work, It Takes a Nation of Millions to Hold Us Back, an album many music historians consider to be the pinnacle hip-hop statement, Public Enemy spearheaded arguably the most exciting rap tour ever conceived.

Encore: Along for the wild ride was the godfather of West Coast rap, Ice-T, who was putting on the rest of the country to Los Angeles’ violent Crips and Bloods gang wars with the too-real “Colors.” N.W.A. was just about to set the world on fire with their opus Straight Outta Compton. Eazy-E, Ice Cube, Dr. Dre, MC Ren and DJ Yella unleashed a profanity-laced declaration of street knowledge that was instantly slapped with parental advisory stickers. And Erick and Parrish were making dollars with their rough and raw EPMD joint Strictly Business.

6. Nitro World Tour (1989-90)

LL Cool J, featuring Public Enemy, Eazy E & N.W.A., Big Daddy Kane, Too $hort, EPMD, Slick Rick, De La Soul and Special Ed

In early ’85, LL Cool J was a 16-year-old rhyme fanatic living in his grandparents’ Queens, New York, home. Three years later, the kid who became Def Jam Records’ signature artist with his iconic B-boy manifesto Radio was the most successful solo emcee on the planet with more than 4 million albums sold and counting. LL Cool J was also headlining some of the hottest events of rap’s golden era. And he was at his cockiest love-me-or-hate-me peak during the Nitro Tour.

But not even LL Cool J was ready for the monster that was N.W.A. The self-proclaimed World’s Most Dangerous Group completely hijacked the spotlight when N.W.A. was warned by officials not to perform their controversial track “F— the Police” at Detroit’s Joe Louis Arena. A minute into the song, cops stormed the stage and shut down Eazy-E and crew’s volatile set, a wild scene that was later re-created in the 2015 N.W.A. biopic Straight Outta Compton.

Encore: A few months before the Detroit gig, N.W.A. was booed during a Run-DMC show at New York’s Apollo Theater. “We all had watched Showtime at the Apollo, so we all knew if it went bad what was gonna happen,” Ice Cube explained on the Complex story series What Had Happened Was … “We hit the stage, and as soon as they saw the Jheri curls, all you heard was ‘Boo!’ I mean, before we even got a line out, they was booin’. I guess they just wasn’t feeling the Jheri curls.”

Rappers Christopher “Kid” Reid and Christopher “Play” Nolan of Kid ‘n Play perform onstage during “The World’s Greatest Rap Show Ever” on Jan. 3, 1992 at Madison Square Garden in New York.

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5. The World’s Greatest Rap Show Ever (1991-92)

Public Enemy, DJ Jazzy Jeff & The Fresh Prince, Queen Latifah, MC Lyte, Geto Boys, Kid ’n Play, Naughty by Nature, A Tribe Called Quest, Leaders of the New School and Oaktown’s 3.5.7.

Props to the promoter who put together this awesome collection of hip-hop firepower for a tour that at least aimed to live up to its tagline. What stands out the most was the early acknowledgment of rap’s reach beyond the East and West coasts. The significance of including Houston’s Geto Boys, for instance, cannot be overstated.

Scarface, Willie D and Bushwick Bill carried the flag for Southern hip-hop, winning over skeptical concertgoers with their raw dissection of ’hood paranoia, “Mind Playing Tricks on Me,” which had become a favorite on Yo! MTV Raps. Jazzy Jeff and The Fresh Prince proved they could still rock the house with PG-rated material. (It helped that Will Smith had just begun the first season of NBC’s The Fresh Prince of Bel-Air.) Queen Latifah busted through the testosterone with the empowering “Ladies First.” And Naughty by Nature frequently knocked out the most crowd-pleasing set of the night with their promiscuous anthem “O.P.P.”

Encore: The World’s Greatest Rap Show Ever made its Jan. 3, 1992, stop at New York’s Madison Square Garden less than a week after nine people were fatally crushed at a hip-hop charity basketball game at City College of New York. Before Public Enemy’s powerful message of black self-determination, Heavy D, an organizer of the doomed event, made a plea for unity. Fans were certainly listening. The gig was a resounding, peaceful triumph.

LL Cool J performs at the Genesis Center in Gary, Indiana in December 1987.

Raymond Boyd/Getty Images

4. Def Jam Tour (1987)

LL Cool J, Whodini, Eric B. & Rakim, Doug E. Fresh and the Get Fresh Crew, and Public Enemy

From 1986 to 1992, New York’s Def Jam Records was the premier hip-hop label. Its roster of artists, which included Public Enemy, the Beastie Boys, EPMD and Slick Rick, was unparalleled in range and cultural dominance. So when it came time for partners Russell Simmons and Rick Rubin to spread the Def Jam gospel on its first international tour, the imprint’s biggest star, LL Cool J, was chosen to lead the way. And he didn’t disappoint.

James Todd Smith strutted out of a giant neon boombox sporting a Kangol hat, dookie rope gold chain and Adidas jacket. Of course, that jacket would soon be thrown to the floor as a shirtless Ladies Love Cool James tore through his ’85 single “Rock the Bells” as if it were the last song he would get to perform.

For many overseas, their first taste of American rap also included DJ Eric B. & Rakim, who were killing the streets with their 1987 masterpiece Paid In Full. Almost overnight in Germany, France, Norway and the Netherlands, hip-hop became the new religion.

Encore: This was the first proper world tour for Public Enemy, who had just dropped their 12-inch single “Rebel Without a Pause.” Although they were the opening act, Chuck D and his posse stole the show, establishing their standing as global behemoths. The now-legendary show at London’s Hammersmith Odeon can be heard throughout It Takes a Nation of Millions to Hold Us Back.

The Up In Smoke Tour in 2000 was a dream team bill, headed by producer Dr. Dre and featuring Eminem, Ice Cube, Snoop Dogg and more.

Photo by Ken Hively/Los Angeles Times via Getty Images

3. Up In Smoke (2000)

Dr. Dre, Snoop Dogg, Ice Cube, Eminem, Tha Dogg Pound, Warren G and Nate Dogg, and Xzibit

As over-the-top, profane spectacles go, the Up In Smoke Tour has few rivals. Detroit’s Eminem stormed the stage wearing a red jumpsuit with “County Jail” stitched on the back. Ice Cube, before being joined by his Westside Connection cohorts, Mack 10 and WC, emerged from a cryogenic chamber. Hennessy-sipping and weed-toking Dr. Dre and Snoop Dogg rode out in a hydraulically juiced lowrider. There was a 15-foot talking skull!

The multimillion-dollar stage design put the concert industry on notice that not only could rap shows attain the lavish production values of the best rock shows, they could surpass them. It was also an emphatic statement that the largely West Coast rap dignitaries knew how to throw a party. And there still isn’t another hip-hop song that matches the first 20 seconds of Dre’s “Next Episode” in concert.

Gross: $22.2 million from 44 shows

2. Raising Hell Tour (1986)

Run-DMC, featuring LL Cool J, the Beastie Boys and Whodini

There’s a reason Run-DMC is hailed as the greatest live hip-hop act of its era. They understood that less is always more. Because of their stripped-down beats and rhymes, the group amplified the genius of every aspect of their concert presentation up to 11. Jam Master Jay’s scratching was more thunderous than the other DJs on the 1s and 2s. Run’s pay-me stage presence commanded respect. And D had the throat-grabbing voice of God. They wore Godfather hats, black jeans and shoelace-less Adidas sneakers. The Hollis, Queens, crew was the personification of cool.

LL Cool J was just 18 during the Raising Hell Tour, but he was coming after Run-DMC’s crown every night. The hotel-wrecking Beastie Boys co-piloted rap’s bum-rush into Middle America, scaring parents wherever they landed. And Whodini brilliantly straddled the line between electro funkateers and around-the-way dudes representing BK to the fullest.

As “Walk This Way,” Run-DMC’s genre-shifting Aerosmith collaboration, exploded on the pop charts, vaulting the Raising Hell album to 3 million copies sold (the first hip-hop album to go triple platinum), ticket sales followed. The 45-city tour affirmed hip-hop’s cultural takeover.

Encore: The image of Joseph Simmons commanding 20,000-plus fans to hold up their sneakers during a performance of “My Adidas” at a New York show is still a surreal sight.

1. Fresh Fest (1984)

Kurtis Blow, Run-DMC, Whodini, The Fat Boys, Newcleus & the Dynamic Breakers, New York City Breakers, Turbo and Ozone

Ricky Walker had an idea: The concert promoter wanted to put together the first national rap music and break-dancing tour. In 1984, hip-hop had moved on from its underground beginnings in the Bronx. Run-DMC had just dropped their self-titled debut, and their “Rock Box” became the first rap video to received play on MTV. Breakin’, the first break dancing movie to hit the big screen, pulled in nearly $40 million at the box office on a minuscule $1.2 million budget. Walker saw the future.

He called New York impresario Simmons to tap some of his Rush Productions talent, which included heartthrob Brooklyn trio Whodini, rap’s first solo superstar Kurtis Blow, the comedic Fat Boys and, of course, the hottest hip-hop act in the country, Run-DMC. But when it came time to promote the first show, billed as the Swatch Watch NYC Fresh Fest Festival, in Greensboro, North Carolina, Walker was laughed out of the room by a radio ad man.

Rap was still viewed by many record industry power brokers as a passing fad. In a 1985 interview with Billboard magazine, Walker recalled the salesperson pleading with him. “You’re a friend of mine,” he said. “Can’t I talk you out of doing this show?”

Walker’s instincts, however, proved to be dead-on. Fresh Fest moved 7,500 tickets in four hours. The tour, which also featured some of the best street dancers on the planet, such as Breakin’ stars Boogaloo Shrimp and Shabba Doo, as well as the synth funk-rap group Newcleus, not only did brisk business at mid-level venues but also sold out 20,000-seat arenas in Chicago and Philadelphia. Like the pioneering rock ‘n’ roll shows of the ’50s conceived by Cleveland radio DJ Alan Freed, the Fresh Fest proved that rap could be a serious and profitable art form. The rest is hip-hop history.

Gross: $3.5 million

Will Smith, a pioneering black nerd, helped raise and change rap music Smith’s music career reveals an artist who believed in an Afrocentric American dream based on ambition, hustle and black pride

It was 2017, and Will Smith’s career seemed to have come full circle.

That’s when a sneak peek video surfaced featuring the world-famous entertainer performing a hip-hop version of the theme from Aladdin, a Disney musical, which opens in movie theaters Friday, featuring Smith in the role of the genie. For fans, the tune conjured memories of Smith’s career-launching hit “Girls Ain’t Nothing But Trouble,” which sampled the theme from I Dream of Jeannie, a 1960s sitcom about a genie.

The coincidence was eerily appropriate. With four Grammys, six American Music Awards, four NAACP Image Awards and two Oscar nominations, Smith’s career has seemed like a magic carpet ride, almost as if a wizard granted his wish of becoming one of history’s most successful entertainers. But while his big-screen achievements have been exhaustively examined, Smith’s musical accomplishments have received shorter critical shrift. From PTA-approved hits such as “Parents Just Don’t Understand” and “A Nightmare on My Street” to party-starting jams such as “Summertime” and “Gettin’ Jiggy Wit It,” Smith’s songs are so cursedly simple that some might argue they’re undeserving of serious critical scrutiny. We’re here to argue otherwise.

Smith’s career has seemed like a magic carpet ride, almost as if a wizard granted his wish of becoming one of history’s most successful entertainers.

Take, for example, the aforementioned Aladdin rap. Like most songs from Smith’s canon, the tune is a bouncy urban jam with lyrics of nursery rhyme simplicity.

“One fine day the bazaar was at peace, when the guards started running through the Agrabah streets

They were lookin’ for a lad and a beast, ’cause they was nabbin’ some yeast

The thickest of thieves in the Wild, Wild East …”

Notice how Smith sets up a story, stoking your desire to learn more. From his very first 1980s hits, he has repeatedly woven fablelike narratives into his songs, a creative device that makes listeners hang onto his every word. In this regard, he has just as much in common with legendary country and western songwriters such as Hank Williams, Johnny Cash and Dolly Parton as with his rapping peers.

Next, note how the line “a lad and” is a subliminal reference to the title Aladdin, while the phrase “Wild, Wild East” alludes to Smith’s 1999 hit “Wild Wild West.” Rap music is a narcissistic genre in which artists’ skills are largely judged by the ingenuity of their boasts. In the Aladdin song, Smith triumphantly toots his own horn while never once name-checking himself, which makes him appear both humble and confident. That’s the kind of skill that helped the Philadelphia native nab the first best rap song Grammy Award in 1989.

The Aladdin promo music video harks back to Smith’s 1990s heyday, when he triumphantly sampled old rhythm and blues and TV theme song tunes packed with sentimental value (Aladdin samples Alan Menken’s theme from the 1992 animated version of the Middle Eastern folk tale). Smith’s rap also marks a return to the days when his songs were movie promotions, and it’s tempting to view his lucrative music career as a byproduct of his movie fame: safe-as-milk family entertainment concealed beneath a fashionable urban disguise. Indeed, Smith’s gentlemanly, glad-handing public image contrasts sharply with prevailing rap iconography, which has become so hard-nosed that most rappers wouldn’t be caught dead smiling in their promotional photos.

But a closer inspection of Smith’s music career reveals an artist who gambled on a personal belief in an Afrocentric American dream, one based on ambition, hustle, black pride and monogamy. His decidedly nerdy worldview has drawn its share of hilarious ridicule and attacks from peers, but in hindsight his ’90s hits now seem almost heroic in their contrarian niceness. What follows is an examination of Smith’s music career, an exploration that reveals how he remained true to his principles at the risk of being labeled a corporate sellout … and in the process became one of the best-selling hip-hop artists of all time.

The Plain Brown Rapper

It was 1988, and Smith was bombing.

Better known by his alias “The Fresh Prince,” Smith and musical partner DJ Jazzy Jeff were onstage at the Greek Theatre in Hollywood, California, opening for the Beastie Boys and Public Enemy. At the time, Smith and DJ Jazzy Jeff (real name Jeff Townes) were savoring the success of “Parents Just Don’t Understand,” the breakthrough single from their multimillion-selling album He’s the DJ, I’m the Rapper. They were 19-year-old millionaires, the darlings of radio and MTV. So why were they being jeered on a Los Angeles stage?

Despite their critics, DJ Jazzy Jeff (left) and The Fresh Prince (right) were the darlings of radio and MTV in 1988, savoring the success of their hit song “Parents Just Don’t Understand.”

Photo by Michael Ochs Archives/Getty Images

The reason was simple — Smith and Townes’ set was a disaster. This writer attended that night, and I recall being agog at Smith’s attempts to transform his performance into an interactive experience, appealing for audience participation as he emulated childhood games. Had smartphone cameras and YouTube existed back then, Smith and Townes might have become instant laughingstocks. Compared with the Beastie Boys’ beer-swilling rowdyism and Public Enemy’s fist-thrusting black militancy, Smith and Townes’ slapstick performance was embarrassingly naive and out of touch.

Other rappers might have taken the hostile crowd response as a cue to change course toward an edgier sound. But not Smith and Townes. They seemed creatively beholden to the early days of hip-hop, when the scene was dominated by boogie-down jams such as “I Can’t Live Without My Radio” and “Big Mouth.” As hip-hop legend William “Flavor Flav” Drayton told MTV in 1999: “I remember rap music. We used to party and dance off of it.”

But the dancing came to an abrupt halt in 1988. It was the final year of Ronald Reagan’s presidency, an eight-year term that saw black communities devastated by a federal escalation of the war on drugs. Nationwide, African American neighborhoods had watched in dismay as a blighting influx of crack cocaine gripped the areas where they lived. In mostly black South Central Los Angeles, police were using military-grade weaponry to confront young black suspects, while East Coast neighborhoods such as Roosevelt, New York, went from middle-class prosperity to abject desolation. “Mostly every household had somebody that was strung out,” said Public Enemy producer Hank Shocklee. “Even my brother had a brief moment being addicted, so it resonated very close to me.”

As if in response to Reagan’s hard-line conservatism, hip-hop got deadly serious. Hard-core rap subgenres that had been gestating underground suddenly began garnering widespread radio and consumer attention. Whether it was the political hip-hop of Public Enemy, the desperado “gangsta rap” of N.W.A. and Ice-T or the Afrocentric “conscious rap” of Gang Starr and the Jungle Brothers, 1988 marked a paradigm shift. Just as the Beatles proved rock music could make broader sociopolitical statements, rap’s Class of ’88 seized on hip-hop’s thematic potential, sowing the seeds of a musical revolution.

Into this chaotic musical fray entered Smith. His initial recordings helped transform rap into a lucrative crossover genre, yet he was already at risk of becoming a has-been. In 1989, he and Townes issued yet another collection of teen-targeted novelty tunes entitled And in This Corner …. The album and its spinoff singles flopped. “It was a tragedy,” Smith recalled in 2018. “[The album] went, like, double-plastic.”

The LP’s failure sent Smith into a downward spiral. Like many nouveau riche overnight successes, he had blown through his fortune while neglecting to pay his taxes, and now the IRS was knocking. “Being famous and broke is a s—– combination,” he would later say, “because you’re still famous and people recognize you, but they recognize you while you’re sitting next to them on the bus.”

Then, fate intervened. Hoping to keep his career afloat, Smith began appearing on The Arsenio Hall Show, a new late-night talk show that was an instant hit with the MTV generation. Backstage during one of his appearances, Smith was introduced to Benny Medina, who along with entertainment legend Quincy Jones was developing a sitcom about his childhood experience growing up with a wealthy Hollywood family. Smith aced his audition, and within months of its 1990 premiere, The Fresh Prince of Bel-Air was the top-rated sitcom of the year.

In one fell swoop, Smith was rescued from near irrelevance, and he would make the best of his second chance. Cautiously embarking on a movie career, he earned all-important Hollywood cred by starring in acclaimed, low-budget art house films such as Six Degrees of Separation and Where the Day Takes You. He was craftily starting with modest projects, methodically inching his way up the Hollywood ladder, demonstrating the shrewdness that would make him a megastar.

Triumph of the Will

It had been years since the sales disappointment of And in This Corner…, but now it was 1991 and Smith was appearing on a talk show touting the imminent release of his first single of the new decade. “May 20, we’ll be premiering our video,” he earnestly told Byron Allen. “We’ve been away for a while, and we’re coming at you spankin’ new.”

Will Smith (left) and Benny Medina (right) attend the premiere of Disney’s Aladdin at El Capitan Theatre on May 21 in Los Angeles. A chance meeting with Medina helped launch The Fresh Prince of Bel-Air, which changed the trajectory of Smith’s career.

Photo by Kevin Winter/Getty Images

The music video Smith alluded to was “Summertime,” a mellow head-bobber that deviated from the madcap mold of previous Fresh Prince/Jazzy Jeff tunes. Featuring a “slightly transformed” sample of Kool & The Gang’s seductive ’70s jam “Summer Madness,” Smith’s retooled version perfectly captured the soulful essence of a midsummer day in the ’hood.

“The temperature’s about 88
Hop in the water plug just for old time’s sake
Break to ya’ crib, change your clothes once more
Cause you’re invited to a barbecue that’s starting at 4
Sitting with your friends cause y’all reminisce
About the days growing up and the first person you kiss
And as I think back makes me wonder how
The smell from a grill could spark up nostalgia …”

Call it a comeback. “Summertime” dramatically reversed Smith’s flagging musical fortunes, selling more than 1 million copies and nabbing the Grammy for best rap performance by a duo or group. But for Smith, the single’s importance went beyond accolades and peer honors. “Summertime” seemed to establish a template for the rapper’s subsequent singles. He would eventually part ways with Townes, embarking on a solo career in which he would apply his rhymes to samples of R&B radio favorites from the post-Motown era, including tracks by Luther Vandross, Stevie Wonder, Sister Sledge, Roy Ayers Ubiquity and others.

His music evinced a sense of elegance and upward social mobility. While he wasn’t above sampling the occasional gutbucket stomp, his biggest singles were assembled mostly from R&B songs produced north of the Mason-Dixon Line, lavish funk hits that lent his music the upscale appeal of a Versace collection. Perhaps the best example of this was “Gettin’ Jiggy Wit It,” the gold-certified hit from Smith’s high-stakes 1997 solo debut album, Big Willie Style. The tune sampled “He’s the Greatest Dancer,” the disco classic that name-checks elite clothing brands such as Halston, Gucci and Fiorucci.

Smith’s musical choices couldn’t have been more perfectly timed. He was launching his solo career in the late ’90s, a period of tremendous economic growth and conspicuous consumption. To underscore the notion that he was a musical status symbol, he crammed Big Willie Style with broadly appealing, expensive-sounding samples. “Men in Black” appropriated Patrice Rushen’s luxurious ’80s shuffle “Forget Me Nots,” while subsequent singles “Miami” and “Just the Two of Us” borrowed from The Whispers’ “And The Beat Goes On” and Bill Withers’ satiny 1981 ballad “Just the Two of Us.” Yet, while his tony, aspirational music matched your Cartier ensemble, Smith’s songs were still down-home enough to be played at the neighborhood block party.

His music may have conveyed sophistication, but his lyrics were pure, old-fashioned hip-hop egomania. Big Willie Style found Smith boasting constantly about his boffo film career while flipping off his detractors (“Player haters been hatin’ all my playin’ for years / Now they seein’ they worst fears as I bathe in cheers”). Yet despite all his Tarzanlike chest-thumping, Smith was careful to promote himself as hip-hop’s resident straight arrow. Where his gangsta rap rivals were dismissing women as “b—-es” and worse, the females in Smith’s songs were “ladies” and “hot mamis.” He trumpeted the joys of fatherhood and celebrated his romance with soon-to-be wife Jada Pinkett (“Finally found a person, worthy of all / Instead of pushin’ me down, you want to cushion my fall / Your eyes could make the sun rise, all the birds sing / Seal it with a kiss, bind it with a ring”).

While his tony, aspirational music matched your Cartier ensemble, Smith’s songs were still down-home enough to be played at the neighborhood block party.

This reconciliation of bravado and gee-whiz humility is classic Smith, and he would be rewarded handsomely for his bluster. Boosted by its status as the theme song from the Smith movie of the same name, “Men in Black” topped singles charts throughout Europe and Australia, capturing the 1998 Grammy Award for best rap solo performance. By the time its initial sales run was through, Big Willie Style had moved 9 million copies, making it one of the best-selling hip-hop albums of all time. In the midst of gangsta rap’s blood-splattered heyday, Smith was topping the charts with obscenity-free songs about clubbing, chivalry … and himself.

Seizing on the momentum of his blockbuster performances in movies such as Independence Day and Bad Boys, Smith released his second solo album in 1999. Willennium spawned the debut single “Wild Wild West,” another movie tie-in featuring a sample of Stevie Wonder’s percolating single “I Wish.” The follow-up single “Will 2K” was built from The Clash’s 1983 funky post-punk classic “Rock the Casbah,” while “Freakin’ It” bummed its beat from Diana Ross’ ritzy disco classic “Love Hangover.” Though not quite the sales bulldozer its predecessor was, Willennium nonetheless penetrated Billboard‘s Top 5 and sold more than 5 million copies.

It doesn’t take an Einstein to see that Smith was trading on musical nostalgia to make his songs broadly appealing, but was that so bad? He had already proved with his movie career that he was a shameless, crowd-pleasing capitalist, so why would his music goals be any different? Black songwriters such as Rushen, Nile Rodgers and Kool & The Gang certainly weren’t complaining about Smith’s sentimental hip-hop — his samples were plumping their bank accounts. He was so good at tapping prime funk hits that an associate of mine described him as an “archivist,” a man who heedfully selects stylish baby boomer jams, then gently contemporizes them for posterity (and lucrative Gen X consumption). Asked about Smith and others sampling his songs, Kool & The Gang’s Robert Bell said, “We feel honored! People are listening to our music.”

Will Smith (left) and Tommy Lee Jones (right) in a scene from the film Men in Black in 1997. Smith’s single “Men in Black” captured the 1998 Grammy Award for best rap solo performance.

Photo by Columbia Pictures/Getty Images

But while millions were buying into Smith’s retrograde rap, others were calling him out. It was rumored that he didn’t write his own songs, although Smith’s collaborators attested to his lyric writing/composing skills. Others attributed his musical fame to his soaring movie career, while others criticized him for trafficking in “nonstop pop-rap clichés.” Worst of all, hip-hop purists viewed him as the grievous poster child for corporate rap, exhuming crossover R&B classics to stroke MTV and Top 40 radio programmers. “Just because a song was fun when I was a kid doesn’t mean the guy who made it isn’t a bit of a crossover clown and has made some of the most embarrassing singles of all time,” wrote one contributor on an online forum.

Comments like these would dog Smith throughout his heyday, making him one of rap’s most controversial artists, and you’d still be hard-pressed to find a hip-hop artist who drives purists crazier. Rap music had always prided itself on salting wounds, whether through its automated, minimalist sound, its uncompromising political stances or its embrace of outlaw stereotypes. But then along came Smith with his “nice, clean rap,” and some folks became unglued.

He was resented for not buying into the myth that black hooliganism is somehow authentic (or “real,” to use the parlance of the ’hood). Smith had chosen to become a symbol of the black middle class, a millions-strong group of gainfully employed, law-abiding African Americans who paid their taxes, maybe attended church on given Sundays, and preferred Calvin Klein and FUBU to gangbanger bandannas. His sampling of opulent funk was a subtle shout-out to a black bourgeoisie the media largely ignored. “It’s real important to have balance of the imagery,” Smith told Billboard magazine in 2005. “Yes, there are people who fire guns in the street, but there’s also doctors who go to work in those areas to feed their children.”

But Smith’s critics were raising even broader questions about crossover and hip-hop’s plagiaristic roots. Why was it a crime for Smith to tap the sentimental value of old funk and pop tunes? After all, The Sugarhill Gang established the cannibalistic rules for hip-hop in 1979 when they executed a verbatim lift of Chic’s “Good Times” for their tune “Rapper’s Delight,” the first rap tune of any consequence. Moreover, amid current debates about cultural appropriation, were rap acts such as Smith, Run-D.M.C. and Public Enemy conducting artistic larceny when they sampled white rock bands such as The Clash, Aerosmith and Slayer? Or were these and other rappers simply flipping the bird at segregationist radio programmers who persisted in compartmentalizing white and black music? Whatever the case, it seemed Smith was being held to a harder standard than many of his peers.

His detractors didn’t seem to take into account that sampling is a statement. During hip-hop’s hypercompetitive golden age, the best rap acts used samples partly as a way to align themselves with certain musicians, philosophies and movements. When Dr. Dre heavily sampled Parliament-Funkadelic on his 1991 magnum opus The Chronic, he was establishing an attitudinal connection between his own laid-back jams and George Clinton’s weed-scented stoner funk. Similarly, Smith’s appropriation of post-Motown R&B seemed like a rational choice, an honest reflection of his middle-class upbringing.

The son of a refrigeration engineer and a school administrator, Willard Carroll Smith II was a Baptist who attended a West Philly Catholic middle school. By all accounts, his was a grassroots upbringing that had little, if anything, to do with hoodlums and black militancy. He was 12 years old when his devoutly Christian grandmother discovered a book of his rhymes, many of them peppered with vulgarities. “Dear Will,” she wrote inside the notebook, “truly intelligent people don’t have to use words like this to express themselves. Please show the world that you’re as smart as we think you are.”

That scribbled rebuke changed Smith. “She made me realize that I wasn’t creating only for me,” he said in 2016. “The things I created were going to have an effect on her and were going to have an effect on everyone who came into contact with my artistry.”

Smith took his grandmom’s advice, and if one examines his music, one will discover a positivist philosophy encapsulated by the title track of his 2002 album Born to Reign:

“I believe in God, I believe in destiny

Not destiny in the sense of all of our actions being predetermined

But destiny in the sense of … our ability to choose who we are, and who we are supposed to be …”

He had molded himself into a massively popular polymath entertainer, a man so sure of his rapping dominance that he flamboyantly christened the 2000s the “Willennium.” His hip-hop future seemed bright and unstoppable.

Then he faded from the music scene.

The smartest dude

In 2005, after a three-year absence, Smith returned to the recording fold with an album entitled Lost and Found. Its cover featured Smith at the make-believe intersection of “West Philly” and “Hollywood” streets, an image that suggested he was at a musical crossroads. That notion was underscored by new songs in which he ditched his vintage funk samples for original beats. Although it spawned the Top 10 single “Switch,” the album ultimately sold 500,000 units, not even close to the performance of his multimillion-selling 1990s CDs.

Though he hasn’t released an album in nearly 15 years, Smith hasn’t vanished into obscurity. To the contrary, he’s leveraging his fame to become a digital influencer. He recently used his Instagram account (30 million followers and counting) to hawk branded merchandise, including a sold-out limited run of Fresh Prince of Bel-Air accessories. More than 5 million subscribers visit his YouTube channel to keep up with him and his family. Smith’s songs are still played across the broad spectrum of African American life: at the club, at parties, at backyard barbecues and family get-togethers. Get a real gangsta liquored up enough and he might confess that Smith jams like “Gettin’ Jiggy Wit It” and “Miami” are on his personal mixtape.

Smith is 50 now, and as he enters the elder statesman period of his career, his legacy seems more wide-ranging than many would imagine. He exists as a genre unto himself, a rapper whose austere lyrics and uncomplicated samples are unique in hip-hop. Although he’s never confessed to such, he was a pioneering black nerd well before the empowering phrase “blerd” was even coined. He played a role in unseating rock ’n’ roll as the favored music of youth worldwide, then helped raise rap music’s international stature by becoming a multimedia megastar.

He recently made a surprise guest appearance at Coachella, arguably the world’s most popular and lucrative music and arts festival. Popping onstage during his son Jaden’s performance, the old man reportedly stole the show, lending credence to his lifelong theory that nice guys finish first. “I’m trying to present … a more sound approach to survival,” he said in 2005. “It’s a more long-term approach based on intellect and skills that can’t be taken away from you.

“The smartest dude survives the best.”

DJ Jazzy Jeff, The Fresh Prince and a Grammy boycott that set the tone for three more decades of rap — and culture ‘Parents Just Don’t Understand’ was the first hip-hop song ever nominated for a Grammy

 

It was 1989. The scene: Los Angeles’ Shrine Auditorium. The host: Billy Crystal, who then was starring in films such as Memories of Me and When Harry Met Sally. The event was the 31st Annual Grammy Awards. George H.W. Bush had recently been sworn in as president of the United States, and the Gulf War would soon be looming. In the last year of the 1980s, pop ruled the Billboard charts but hip-hop continued its rise in sales and its impact on culture. Pioneers such as Public Enemy, Heavy D, 2 Live Crew, The Beastie Boys, Queen Latifah, Big Daddy Kane, De La Soul, Special Ed, 3rd Bass, Boogie Down Productions and more were changing music and the music industry.

That night though: Bobby McFerrin, would-be 10-time Grammy winner, won song of the year and record of the year for “Don’t Worry Be Happy.” The song was McFerrin’s only No. 1 hit and had a layer of controversy attached, as it had been used by the Bush presidential campaign in 1988 without the permission of McFerrin. In protest, McFerrin for years removed the song from his concert set lists. The televised broadcast of the Grammys also featured what would become a legendary performance by Whitney Houston — she sang her “One Moment in Time” against a montage backdrop from Team USA highlights of the ’88 Olympics.

But it’s what didn’t happen during the televised broadcast of the 31st Grammy Awards that made the 1989 event even more memorable. DJ Jazzy Jeff & The Fresh Prince, aka Jeff Townes and Will Smith, who had been nominated for the first-ever best rap performance Grammy for their hit crossover single “Parents Just Don’t Understand,” were not there to pick up their award. When it had been decided that the only rap award would be announced during the nontelevised portion of the show, hip-hop had its own decisions to make. “We chose to boycott,” Smith said at the time. He called the idea of the afternoon award a “slap in the face. … You go to school for 12 years, they give you your diploma and they deny you that walk down the aisle.”

Besides Jeff and Will, the other first rap Grammy nominees were:

All of these songs had been released one, two or, in the case of “Push It,” even three years before. Hip-hop by 1989 was going through a transformation. The anger was no longer mostly underground but rather more out front. Public Enemy would release its critically acclaimed Fear of a Black Planet in 1990, and the cracks in the foundation of revolutionary supergroup N.W.A. were beginning to show.

DJ Jazzy Jeff & The Fresh Prince were in a playful, more mainstream rap lane that included MC Hammer and his diamond 1990 Please Hammer, Don’t Hurt ’Em. “Parents Just Don’t Understand” peaked at No. 12 on Billboard’s pop singles chart, but it was the building momentum that DJ Jazzy Jeff & The Fresh Prince saw on one of their first big tours that cemented for the West Philly duo what everyone else was seeing. “We were on the road, so we had no idea how the record was doing on the radio,” Jazzy Jeff said in Brian Coleman’s Check the Technique: Volume 2: More Liner Notes for Hip-Hop Junkies. “I remember one night … Will did the first verse and then did the first line of the second verse, but told the crowd to finish it. And I thought, Oh, no, this could be the biggest disaster in the world! But … 20,000 people finished the verse.”

Rap was still considered a fringe force, fighting not only for its place at the Grammy Awards but also for acceptance as a respected musical genre.

MC Hammer’s massive sales numbers, though, were the exception at the time for hip-hop, not the rule. Rap was still considered a fringe force, fighting not only for its place at the Grammy Awards but also for acceptance as a respected musical genre. It was just that fight and the almost constant controversy surrounding hip-hop that fueled its ascent to being the most popular musical genre in the world.


The news started out great. The National Academy of Recording Arts and Sciences (NARAS) had announced that rap would have its own official category. “The excitement was through the roof,” said Jazzy Jeff. “It was validation for the culture.” But when the news quickly turned bittersweet, Russell Simmons and Lyor Cohen of Def Jam Recordings led a boycott of the 1989 Grammys. Joining them were the Fresh Prince and Jazzy Jeff along with Salt-N-Pepa, Public Enemy, Ice-T and others. Def Jam spokesman Bill Adler’s press release said that NARAS was “ghetto-izing” rap. The boycotting group even held a “Boycott the Grammys” party on the night of the broadcast.

The show wasn’t an all-out rap boycott, however. JJ Fad attended, as did Kool Moe Dee, who presented the embattled best rap performance award at the pre-show, saying, “On behalf of all MCs, my co-workers and fellow nominees — Jazzy Jeff, J.J. Fad, Salt-N-Pepa and the boy who’s bad — we personify power and a drug-free mind, and we express ourselves through rhythm and rhyme. So I think it’s time that the whole world knows rap is here to stay.”

The “boy who’s bad” refers to his rival LL Cool J. Years later, Moe Dee told The New York Times that he believed a better strategy than boycotting would have been for all the artists to show up and “make our case in that space where the world was watching.” Except, of course, that world wouldn’t have been watching the nontelevised version of the show.

One person who did agree with the boycott and believed it ultimately helped the duo cement their place in hip-hop was one of the producers of “Parents Just Don’t Understand,” Ruffhouse Records founder Joe “The Butcher” Nicolo. “It was important to make that stand,” said Nicolo. “I actually thought it would help them. They weren’t bowing down to the Grammy gods, and people respect you for that.”

Not even a Grammy slight could take the shine off “Parents Just Don’t Understand.”

Rap duo DJ Jazzy Jeff and the Fresh Prince perform onstage at Nassau Coliseum on August 12, 1988 in Uniondale, New York.

Al Pereira/Michael Ochs Archives/Getty Images

Also supporting the boycott was DJ Jazzy Jeff & The Fresh Prince’s A&R representative at the time, “Tokyo Rose,” aka Ann Carli. “I supported the boycott,” recalled Carli. “Jive Records was always very supportive of artists.”

The stance taken by Smith and Townes in 1989 is difficult to imagine now. At the 58th Grammy Awards in 2016, Kendrick Lamar’s To Pimp A Butterfly was nominated for album of the year. And while the album didn’t win, it was a reminder that rap music is no longer a fringe genre but rather the most important and influential music in the world. But for every Kendrick moment, there is another example where what Smith, Townes and others fought for seems to be all but forgotten — like at the 57th Grammy Awards in 2015, where no rap awards were presented on the televised broadcast for the first time in 25 years.

Looking back on the protest in 2016, Jazzy Jeff (at this point with four Grammy nominations and two wins) said he felt that he and Smith (at this point with eight Grammy nominations and four wins) represented the culture well and ultimately had an impact. “We … were very, very young and thrust into a position with the eyes of the world on us,” he said. “And to see somebody like Kendrick … it just makes you proud.”

Not even a Grammy slight could take the shine off “Parents Just Don’t Understand.” Its success, and how it sparked the duo’s careers and the meteoric rise of Smith as a Hollywood heavyweight, is stunning. Carli recalled shooting the video for the single, which was done in one 18-hour shoot, and then watching the footage with director Scott Kalvert.

“Holy crap, the camera loves [this kid],” Carli remembers saying. “He’s so incredibly expressive, and he’s selling the story. I called my boss and I said … ‘You know, this kid is going to be a movie star. I think he can be as big as Eddie Murphy.’ ” Carli then proceeded to call Simmons, who managed the duo at the time, to share her feelings about the budding star. Famously, Simmons told Carli that he might be as big as Malcolm-Jamal Warner, but not Eddie Murphy.

Except for Lil Yachty as someone who presents a similar youthful, colorful vibe, Carli doesn’t see many who compare to DJ Jazzy Jeff & The Fresh Prince in today’s current rap climate. “They had a real love and understanding of the genre,” said Carli. “These young rappers don’t seem to have a knowledge and appreciation for the history and the shoulders they’re standing on. … Still to this day, Will is where he is because of his self-confidence, talent and, as Quincy Jones would say, his ‘ass power’… he sticks in the chair until it’s done.”

But as the 60th Grammy Awards approach, the best rap performance award features a class of nominees who each represent something special and also build on the foundation of what DJ Jazzy Jeff & The Fresh Prince and their peers did three decades ago:

  • Kendrick Lamar: The collective spirit of the West Coast
  • Jay-Z: A connection to four different decades of rap
  • Migos: The youthful spirit of the genre today
  • Big Sean: The holding of lyrics in high regard
  • Cardi B: A new rap superstar

Daily Dose: 9/14/17 Is President Trump becoming a team player?

All right, kiddos, if you missed it, I made my second appearance on Around The Horn on Wednesday. I’ll be on again Thursday, so that’s fun too. Tune in, 5 p.m. on ESPN.

Wednesday night was a doozy at Fenway Park. Some people unfurled a sign reading “Racism is as American as baseball,” not a particularly controversial topic. But because it was on the field of play, it had to be removed immediately. Well, let’s just say this was a little awkward overall, considering where this went down. You might recall that a fan yelled racial slurs at Adam Jones there, and, yanno, it’s Boston. We’re not quite clear on who is responsible, but who cares. The message is accurate.

When you’re a black boy, certain things are expected of you. You’re expected to be smart, but not so smart that you make people feel dumb. You’re expected to be tough, but not so tough that if someone insults you, you clap back. You’re expected to be strong, but not so strong that if challenged you actually hurt someone. It’s a vicious form of programming that in turn creates an emotional scale that makes it nearly impossible to emote effectively when something goes wrong. It’s not easy for a grown man to learn to cry.

Nobody knows what President Donald Trump is doing. After a pretty tenuous relationship with the Democrats, suddenly he’s decided to work with them. Now that he’s in such a quandary with the Deferred Action on Childhood Arrivals program, he has to do something. The problem is that he played this backward politically. By first saying that he would rescind it before using it as a piece of negotiation, he’s compromised his own position. In short, it looks like he’s caving because he finally figured out that, hey, “this is how politics works.”

If you’ve ever seen Last Chance U, you know how serious it is. Basically, it’s about football players who’ve had trouble staying around programs for one reason or another in their careers, but sometimes it doesn’t work out. Now, two of the brothers featured in the show are being charged in connection with a stabbing in Tennessee. The two didn’t have the easiest upbringing, but seeing it come to this is heartbreaking. They weren’t the only ones charged in the situation.

Free Food

Coffee Break: If you’re a real Beastie Boys fan, you know that Adam “MCA” Yauch insisted that the band’s music never be used to sell products. So when he died, it was one of the legacies that he left behind. But, also, Mike D and Ad Rock have made exceptions since his death and have recently made another. That’s their choice, I guess.

Snack Time: Good news, NFL fans: Games are actually getting shorter! Oh, you had no idea that was even part of the plan, and you didn’t even notice? That’s probably a good thing too.

Dessert: Here’s a video of Yung Joc in a dress. That is all.

 

Chuck D, B-Real and Tom Morello’s Prophets of Rage arrive just in time to front the musical resistance The rap-rock supergroup is ready to meet all challenges

Chuck D was adamant. The legendary Public Enemy rapper had consented to a phone interview to discuss his latest project, the rap/rock supergroup Prophets of Rage featuring members of Cypress Hill and Rage Against the Machine. But no sooner had the interview begun than Chuck firmly stated that he would only discuss his new group. Presumably, that meant no questions about Public Enemy’s new album, Nothing is Quick in the Desert, nor the recent lawsuit filed against Public Enemy by the group’s iconic hype man, Flavor Flav.

“Right now, my head is propped up trying to remember these words for the next gig,” Chuck D explained from his Boston hotel room, where Prophets of Rage were set to perform at the Paradise Rock Club. “That’s my hardest obstacle right now. Not writing, not recording, but remembering the new songs that I wrote.”

But the tension eased to the point that Chuck D revealed a surprisingly self-deprecating sense of humor, like when the rapper admitted to enjoying splitting interview duties with bandmate Tom Morello. (“Backing him up on interviews allows me to be funny and dumb sometimes, which is good,” he said, laughing.) During another point in the interview, Chuck D got excited confessing his unabashed love for Dollar General stores. “I’m in there all the time!” he exclaimed. “It’s the only place people can come in and get bags and bags of s— for $20. You can’t pass up the deals!”

With superherolike timeliness, Prophets of Rage seemed to arrive just in time to front the musical resistance.

Such humorous asides are in contrast to the recriminations featured on Prophets of Rage, the self-titled album by the band Chuck D recently co-founded with Cypress Hill rapper B-Real, Public Enemy turntablist DJ Lord, and Rage Against the Machine’s Morello (guitar), Tim Commerford (bass) and Brad Wilk (drums). Slated for a Sept. 15 release, the album distills the best of its members’ respective bands, with Morello’s steely guitar riffs hearkening back to the late ’70s heyday of classic rock. Whether rapping about homelessness (“Living on the 110”), marijuana legalization (“Legalize Me”) or President Donald Trump administration (“Hail to the Chief”), Chuck D and B-Real’s vocals lend authentic hip-hop gravitas to the proceedings.

While Prophets of Rage sounds effortless and unforced, Chuck D suggests he and his bandmates feel big-time pressure to deliver. “On paper, this band looks like a no-brainer … so the biggest thing is being able to live up to that,” he said. “We had some mountains to climb performancewise and recordingwise, and it was our goal and obligation to climb those mountains.”


According to Newtonian physics, for every action there is an equal and opposite reaction. That would be a scientific way of explaining the dramatic emergence of Prophets of Rage, a band named after a classic Public Enemy song. In keeping with the revolutionary legacies of their original bands, Prophets of Rage answered the Trump campaign by staging guerrilla performances outside the Republican National Convention in Cleveland. The band then heralded its arrival with a five-song EP entitled The Party’s Over, featuring rocked-up covers of songs by the Beastie Boys, Public Enemy and more. With superherolike timeliness, Prophets of Rage seemed to arrive just in time to front the musical resistance.

But alas, Chuck D is a reluctant caped crusader. “You don’t wish for the world to be f—ed up just so you can be a great band,” said the Hall of Fame MC. “We travel the world to reflect the world’s issues, and to see if we can tie it all together in a concise story. Instead of this belief that a problem has got to be in the United States for you to [care], we say, ‘Here are problems in Sierra Leone or Myanmar that you should also be aware of and have concerns about.’ And if somebody doesn’t get it in Arkansas, or lower Manhattan, or Los Angeles, you say, ‘I’m trying to give you some education, if you give a f—.’ ”

To get that message across, Chuck D knew Prophets of Rage had to compose compelling original songs that rivaled their past works. Toward that goal, he, Morello and B-Real teamed with producer Brendan O’Brien and put noses to the grindstone. The funk-inflected rock songs that eventually materialized forced Chuck to rethink his place within the band. Ultimately, the rapper elected to take a back-seat role, providing counterpoint to predominant rapper B-Real, much in the way that Flavor Flav counterpoints Chuck D in Public Enemy.

“You don’t wish for the world to be f—ed up just so you can be a great band.” — Chuck D

“When B-Real came into the picture, it clicked for me,” Chuck said. “I knew my role wouldn’t be as somebody upfront, but rather as somebody that’s kind of in the shadows. I relished the opportunity to do something different.”

The Prophets’ ideological agenda was articulated on the song “Unf— the World,” wherein the band urges listeners to agitate for positive social and political change (Stand up and rise like the tide/ … no fear, bear witness!). The song title was created by guitarist Morello, whose unflagging faith in grass-roots activism has earned him a reputation as one of rock’s most outspoken and knowledgeable musicians. “Tom has this clear belief that the world won’t fix itself,” Chuck D said. “You’ve got to get up to make these changes.”

Like bandmate Morello, Chuck D has made social uplift a lifelong goal. The rapper surfaced 30 years ago with Public Enemy’s game-changing debut album, Yo! Bum Rush the Show. A veritable explosion of automated rhythm, artful sampling and taunting rhyme, the album poised Chuck D as agitator-in-chief, his clarion voice penetrating the musical bombast like a civil defense siren. Subsequent albums — most notably 1988’s It Takes A Nation of Millions to Hold Us Back and 1990’s Fear of a Black Planet — found the group making good on its initial potential. Public Enemy’s increasingly Afrocentric, conspiratorial stance was illustrated in the band’s stark logo: a black man caught in the crosshairs of a gun’s telescopic sights.

Today, Public Enemy is in the Rock & Roll Hall of Fame, and the group’s first three albums rank among Rolling Stone magazine’s 500 Greatest Albums of All Time. It remains to be seen whether Prophets of Rage will be received as warmly as Chuck D’s past work, but for now the rapper just seems proud to have made a recording that meets his discerning standards.

“I don’t go into the making of any record saying, ‘This record is gonna be what it’s gonna be,’ ” Chuck D said. “I know that when I made It Takes a Nation … with my guys, we knew nothing was like it. So that was our advantage. With [Prophets of Rage], I know there hasn’t been a lineup this significant in its combination of rap, rock and turntablism. … So this record is a reflection of the challenge that we experienced in getting together and pulling it off. I think we met that challenge.”