The 30 Worst Fall-Offs in Rap History

The 30 Worst Fall-Offs in Rap History

The bigger they are, the harder they fall, and no one sits higher than a rapper at the top of his (or her) game. But what might seem like an endless joyride can come crashing down at any time, due to label issues or changing tastes, even something as trivial as a dumb outfit.

While these acts may be gone, they will never be forgotten; we celebrate their peaks and, when it comes to valleys, we reminisce over them. 

30. Charles Hamilton

Interscope Records, the most prominent rap label in the 2000s and home to Dr. Dre, Eminem, and 50 Cent, had finally found the next cornerstone to their franchise, a formerly homeless young man from Harlem named Charles Hamilton. Charles seemed to have all the pieces in order: a very interesting story and point of view, the same powerhouse lawyer as 50 and Eminem, the same A&R who was involved with Kanye and Soulja Boy, a co-sign from DJ Skee, a viral video where he held his own freestyling with Game and Ye, a rapidly growing buzz online, and what many labeled sheer genius.

After releasing two handfuls of mixtapes during the summer of 2008, and on the eve of debuting music from his first album, a series of events over the course of just a few months caused the house of cards to fall apart. Charles claimed he was dating Rihanna. Charles lost in a rap battle at Penn State. On camera. Charles made fun of his girlfriend's abortion and she punched him in the face. On camera. Charles gave J.Dilla executive producer credit on his album, having had no discussion with Dilla's family or estate, and stirred up a great deal of anger from the city of Detroit.

Charles was dropped from Interscope. Charles was arrested in Ohio. Charles took to a wheelchair and was hospitalized for mental reasons. Four years (and an Internet lifetime) later, Charles is attempting a comeback. On his own.

29. Jungle Brothers

By the late 1980s, the Native Tongues movement had reached critical peak, stretching outward from the suburb to suburb. (Weird that such an Afrocentric movement attracted such a white following.) The Jungle Brothers were forebears of hip-house, their single "I'll House You" becoming popular on Club MTV, urban radio, and college campuses.

Straight Out the Jungle, their debut album, got high marks from everyone including Robert Christgau, who compared their output to "an early Bambaataa jam with comic timing." Their second album somehow managed to earn even higher marks from critics, but fell way, way short when it came to sales.

And then, when submitting songs for their third album, 1993's J. Beez with the Remedy, Warner Bros. consistently rejected everything the Jungle Brothers offered up, deeming their sounds too experimental. So, you end up with a product that's too straight-forward for anyone to really grasp onto and, unsurprisingly, no one bought it. So they got dropped by Warner and picked up by the much smaller Gee Street Records, which is why you never heard from them again.

28. Kool Keith

As one of the Ultramagnetic MCs, Kool Keith's rhymes were already different from the rest: "Their rhymes are pathetic, they think they copacetic," as he said on 1988's "Ego Trippin'." Four LPs later, Kool Keith stepped out on his own, releasing 1996's Dr. Octagonecologyst, his concept album earning hyperbolic praise from all corners. 

He was abstract and funny; surreal and explicitly pornographic. (I mean, check the title.) Pitchfork and ego trip both said that it was one of the best albums of the 1990s, the pinnacle of horrorcore.

But ever since, instead of being more pointed and assured, he's become just plain weird, spiraling into his own headspace. (Self-indulgent is a term that could apply here.) And so his albums keep coming, but no one cares anymore. Kool Keith probably never intended to be popular, but he also couldn't have wanted to be ignored.

27. Canibus

In the mid-1990s, Canibus was heralded as THE up-and-coming rapper to watch, after a legendary cypher with members of Wu-Tang, a co-sign from Wyclef Jean, and a verse on LL Cool J's "4,3,2,1" alongside Redman, Method Man, and DMX.

LL took great exception to Canibus' opening line, "Yo LL, is that a mic on your arm? Let me borrow that," and went in on a rapper—seemingly Canibus—during his own closing verse.

The beef escalated into vicious verbal attacks through songs, including the first single from Canibus' Wyclef-produced debut album, Can-I-Bus. A ton of critical poo-pooing, a gold-flaked spray-tan, and almost twenty years later, the very-lyrically gifted Canibus is but a footnote in LL Cool J's IMDB profile.

26. The Pharcyde

An alternative hip-hop group reigning from Los Angeles, The Pharcyde (Imani, Bootie Brown, Slimkid3, and Fatlip) were first a group of dancers, who were only seriously rapping for about a year by the time they recorded their first demo in 1991. They linked up with producer J-Swift and the record label Delicious Vinyl for their debut album, Bizarre Ride II The Pharcyde, which included the crossover success, "Passin' Me By."

But soon enough, the ride turned into a Behind The Music episode, with J-Swift's crack addiction, group infighting, low record sales, and the bitter departures of Fatlip and Slimkid3. Ego over collaborative art may seem backwards, but that's what The Pharcyde was, as evidenced in their Spike Jonze-directed music video for "Drop."

25. Boot Camp Clik

Boot Camp Clik, the supergroup Voltron'd together out of Brooklyn emcees, was a breath of cigarette air in the 1990s. There were assorted pieces: members from Smif-N-Wessun, Heltah Skeltah, Originoo Gunn Clappaz and Black Moon, fastened with staples and rubber bands. As separate entities, they were each buzzing: "How Many MC's...", "Sound Bwoy Bureill" and "I Got Cha Opin (Remix)" are all still played in New York.

The crew teamed up once before "Headz Ain't Redee" off of the New Jersey Drive soundtrack, those two songs setting all of the hype in motion. (It's a well-known story that Tupac invited label head Dru Ha, Black Moon's Buckshot and the guys from Smif-N-Wessun out to L.A. to record with him.)

But when the entire Boot Camp Clik tried to do a full-length project together, in 1997, they could never capitalize; some blame it on the fact that they went with live instrumentation instead of their reliable production team Da Beatminerz. Then there were label problems and personnel problems and problem problems. They recorded some more together, but it seems like they blew their first and only shot.

24. Onyx

Onyx came out of Queens, seemingly on a tireless mission to break necks, heads and eardrums. "Slam" put them at the top of the charts, the hard-hitting hardcore grumbler somehow performing better on Billboard with pop audiences than hip-hop/R&B crowds. (Their album was called Bacdafuckup—who would've thought?)

They continued to put out minor hits throughout the 90s and early 2000s, but emcees Sticky Fingaz and Fredro Starr mostly stayed in the picture by acting in front of the cameras. While that might not sound so bad, just take a second to remember the short-lived TV show Dance 360, a pathetic mid-morning breakdance competition where Fredro played second banana to Kel Mitchell. Yes, of Good Burger fame.

23. Shyne

In the late 1990's Shyne was supposed to be the next in a solid line of Bad Boy success stories. Puff Daddy (Diddy) had deftly guided the careers of Craig Mack, The Notorious B.I.G., Ma$e and others to great heights, but this new young gun, Shyne, was to top them all. And he came out guns blazing, on tracks like "Bad Boyz" and "Bonnie and Shyne," with some critics, for better or worse, comparing his vocal stylings to Biggie.

But the train went off the tracks when on December 27, 1999, Shyne accompanied Puff and his then-girlfriend Jennifer Lopez to Club New York. Three people were injured in a shooting that Shyne was charged with; Diddy and J.Lo got off. Shyne went on to spend eight years in jail, convicted of attempted murder, assault, and reckless endangerment.

His musical ambitions obviously never came to fruition, with a few short-lived post-Bad Boy record deals. Today, Shyne resides overseas, his rapping style is best described as "hurting," and has only gotten attention for the many figurative shots he's taken at Diddy, 50 Cent, Rick Ross, and others. Much like Biggie, Shyne's career was ended far too early.

22. House of Pain

The rap group House of Pain—Everlast, Danny Boy, and DJ Lethal—released their debut album, House of Pain, in 1993. It contained the super-smash-mega-hit song, "Jump Around," which reached No. 3 on the US singles charts, No. 6 in Ireland, and No. 8 in the United Kingdom.

Songs off their follow-up album received little radio rotation, and sales numbers echoed that; a break-up followed not long after. House of Pain may not have had longevity, but "Jump Around" sure did—there's not a sports arena in the country where the song is not played to this day.

21. Young Buck

G-Unit started with 50 Cent, Lloyd Banks, and Tony Yayo. A combination of hubris and label pressure from Interscope's Jimmy Iovine led the imprint to expand to the West for Game; the South, Young Buck. (Game clearly, uh, didn't work out.) Buck was more reliable and less prone to craziness: he stuck by the mercurial 50 through beef after beef; he made some good records that sold well (one platinum!).

But then, in 2007, Buck made some statements that led 50 to think he wasn't being loyal, giving Fif the reason he needed to kick the Tennessean out of the group. Egad! So, then there was a flurry of diss records between ex-employee and onetime boss, which wasn't that interesting until 50 released an audio recording of Young Buck crying on the phone, begging to be let into G-Unit again. Buck claimed the recording was doctored, but it didn't matter: people had long before tuned out.

20. Lil' Kim

People might think it's Nicki's fault that Lil' Kim is on this list, but her downfall started way before Ms. Minaj ever put a wig or even a British accent on. Coming onto the scene in the mid-90s, Kim was a bitch of the finest pedigree: sex, smarts and Biggie's rhymes (literally). She went platinum, won Grammys, and had a course taught about her at Syracuse University.

But then she went to prison in 2005; Atlantic pushed her album out while she was behind bars, and it flopped. Dancing with the Stars, reality shows and her label dropping her: none of it helped. And that was before she started pulling Nicki's weave out of jealousy, before she made people pay for a mixtape that never arrived, and before her plastic surgery became a go-to joke for lazy comedians. That being said, Nicki's heavy-handed swagger-jack certainly didn't help.

19. Black Sheep

Ah, Dres and the other guy...they seem to be the forgotten duo of the Native Tongues clique. To put it quite literally (which is super-unfortunate): they are the black sheep of that time and that place. But for a moment, they were the future: their first release, A Wolf in Sheep's Clothing, is considered a classic by many, one of the best debut rap albums ever. It went gold off of the strength of three Top 10 hit singles on rap radio ("Flavor of the Month," "The Choice is Yours," "Strobelite Honey"), as well as solid word-of-mouth.

Everything looked bright, until it didn't: their follow-up, Non-Fiction, only peaked in the triple-digits on the Billboard 200 chart, and then they were gone. Their legacy, too, has been tarnished: people now think of the staple "The Choice is Yours" because Kia Motors took the song, animated some dancing guinea pigs, and made a Super Bowl commercial out of it. This was all against Black Sheep's wishes, for what it's worth, which is not much.

18. Foxy Brown

Inga Marchand was once the toast of the rap town: she was a platinum-selling artist at 18, she was a protégé of Jay-Z, and considered lyrically gifted enough to be a part of the supergroup The Firm. But any musical success for the sexy Brooklynite was undermined by her attitude, a myriad of assault charges, and most notoriously, the almost-complete loss of her hearing for over a year, during which she refused to wear a hearing aid. In a very short amount of time, Foxy went from the baddest female rapper to the baddest female rapper.

17. EPMD

Erick Sermon and Parish Smith once formed one of the most influential rap groups ever, Long Island's own, EPMD. Their sample-driven songs and back-and-forth rhyming schemes blended together to make classic albums like Strictly Business and Unfinished Business.

But record label business—messy contracts, distribution, and management—led to the group's downfall...well, that coupled with the time that Parish Smith's house was robbed, and one of the burglars said that Erick Sermon paid them to commit the crime.

Tensions, not surprisingly, grew, and EPMD was no longer. Over the last 20 years, there have been reconciliations and break-ups, recordings and near-death experiences, but never success like the late 1980s brought.

16. Slick Rick

Throughout the mid-80s, Slick Rick—eyepatched and accented—appeared all over MTV's airwaves, rapping "La Di Da Di" and "The Show." He dripped gold and fur, an opulent man in a time of extravagance. In 1990, though, it all ended. Rick the Ruler shot two men (one of them his cousin-slash-bodyguard) in revenge for an attempted shooting on his own life.

Prison can stop a career arc real quick, though not in this case: four years after his release, he put out his fourth album—1999's The Art of Storytelling—which quickly went gold. No, it wasn't the shooting or jail that did him in, but rather the deportation issues that stemmed from it. For years, Slick Rick battled the feds over whether he could live and work in this country, biding his time in Rikers while it was all figured out. (In 2008, New York's governor David Paterson pardoned his murder, which has allowed him to stay.)

15. Vanilla Ice

Vanilla Ice, born Robert Van Winkle, took the world by storm in 1990 with his track, "Ice Ice Baby." Not only was he the first commercially successful white rapper, he was the most successful rapper, period, having gone straight to the top of the Billboard charts and selling 11 million copies. His very-white look, his commercial achievements, his dancing, his seemingly struggle-free upbringing, his over-the-top lifestyle, his run-in with Suge Knight, his drug abuse, his suicide attempt, his new grunge-inspired looks, and his refusal to acknowledge the past all played a part in his undoing.

Today, he's rebounded to be an accomplished real estate builder and developer, as seen on his DIY-Network show, The Vanilla Ice Project.

14. Cypress Hill

Cypress Hill, South Gate, California-born weed-friendly rap group were in the early 1990'\s arguably the biggest name in hip-hop. In 1993, their second full-length, Black Sunday, debuted at the top of the Billboard charts, which was at that time the highest charted position for a rap album. Even more impressive, their first album, Cypress Hill, was still in the top ten—also a first for hip-hop. Black Sunday went on to go triple-platinum, thanks to the success of their monster song, "Insane in the Brain."

The following couple of decades have seen the group appear regularly in High Times magazine, though never high on the charts.

13. KRS-One

KRS-One, one-half of the famed Boogie Down Productions, is celebrated as one of the keepers of hip-hop, the embodiment of each of the four elements of the culture. Remembered for cutting down MC Shan with his song "South Bronx," as well as the seminal album Criminal Minded, KRS went on to lead the Stop the Violence Movement and continue to preach the gospel of hip-hop.

Commercially though, KRS' relevance took a dip in the early-to-mid 1990s, as he explored different musical collaborations and spoke more openly about religion and politics. In 2008, BET presented KRS-One with a Lifetime Achievement Award—an honor typically is given at the end of one's career.

12. Raekwon

How do you follow up one of the most celebrated solo debuts ever? How can you top a classic album? Where do you go from the critical apex? In Raekwon's case, the Wu-Tang member took 15 years after Only Built For Cuban Linx... to put out a proper sequel. Let's just say that the music Rae produced in that decade and a half may have happened, but it definitely wasn't remembered.

11. A Tribe Called Quest

A Tribe Called Quest's albums The Low End Theory and Midnight Marauders are considered sacrosanct, debated on the daily, as to which one is more perfect. In so many hip-hop heads' minds, Q-Tip, Phife Dawg, Ali, and Jarobi could do no wrong. Unfortunately, the same sentiment wasn't shared within the group.

As was revealed in Michael Rappaport's documentary, Beats, Rhymes & Life: The Travels of A Tribe Called Quest, when Phife moved to Atlanta after the completion of Marauders, things done changed musically and personally. After they put out Beats, Rhymes and Life in 1996, Phife contends that Q-Tip decided himself that the group had gone as far as it could go; and that was that. ATCQ later reconciled and toured (which begat the documentary), but have yet to record another album.

10. Eazy-E

Eazy-E originally just owned the label; his rhymes were largely written for him by Ice Cube and MC Ren. And yet he grew into one of the most compelling rappers of the 1980s, his high-pitched voice somehow able to sell both humor and reckless menace. On his Eazy-Duz-It and NWA's Straight Outta Compton, Eazy and his friends portrayed gangland L.A. as an exaggerated wonderland, where women were playthings as much as guns and 40s. They found quick success, their gritty street tales crossing over to the suburbs.

But with money came problems. Ice Cube left the group; his "No Vaseline" is a withering diss track, in which he calls out the remaining members of NWA—and Eazy especially—for being frauds. (A sample line? "I kept on stomping while y'all motherfuckers moved straight outta Compton.") The rest of the group escaped Eazy's grip soon after, aided by Suge Knight and company, and his fortunes dropped quicker than a 6-4. Eazy never got the chance to rebuild, as he died soon after, in 1995. 

9. LL Cool J

It's especially sad to watch LL Cool J fall off, considering he built what so many stand upon. That was him in the Kangol and adidas; that was him screaming "Don't call it a comeback/I been here for years!" in 1991. "Doin It" and "Loungin" still sound fresh today, but that was over a decade and a half ago; somehow, LL's still aiming for middle school girls' ears like a wet willy. (He also appeals to moms, though no one in between. Might have something to do with the lip-licking.) Now he's got one foot in corny and the other in irrelevant: he recorded a song based around the CBS show NCIS, and recently put out another called "Ratchet." Someone tell this old man to grow up.

8. Big Daddy Kane

Thanks to songs like "Raw" and "Ain't No Half Steppin", Big Daddy Kane emerged in the late 1980s as one of the leaders of the hip-hop pack, showing off his fast-rapping and his unique fashion style. In the early 90s, Kane was gracious enough to bring Jay-Z on tour and let him show off on stage during costume changes. And while Kane won a Grammy Award in 1991, he was already on a commercial downswing by the time he showed off his "skills" in Playgirl Magazine and Madonna's Sex book; he never got it up again, so to speak.

7. Ice Cube

Ice Cube, known for his deadly rhymes and vicious scowl (literally the face of gangsta rap), was the meanest of the N.W.A. bunch, and a further force to be reckoned with once he went solo in December 1989. His albums AmeriKKKa's Most Wanted, Death Certificate, and The Predator were as stylized as they were controversial, and his multi-platinum sales set him on a course to dominate the musical world...until his audience moved on in 1994.

Perhaps seeing the winds changing, Cube shifted into the world of film, where slowly but surely, his starring roles became family friendly and family friendlier in flicks like "Are We There Yet?" Associated today way more with his acting than his rapping, it's like new Cube killed old Cube—most likely with kindness.

6. DMX

If rap sheets were Billboard lists, then DMX would be running the game today. Alas. DMX's journey from the top to crack rock bottom began in 2004, when he showed up at JFK airport pretending to be a federal agent in order to get through security. (Unsurprisingly, he was in possession of drugs and guns, though not his marbles.) X had legal problems going back as far as 1998, but somehow his rape and assault charges got dismissed; this was when the tide turned.

After that, every month there seemed to be another news item about DMX doing something wrong. For a time, the only constant was that DMX was in jail, somewhere. Finally out of prison, it's too bad that his music isn't connecting with anyone. He's more likely to be on the radio to make fun of Drake than to have his songs played.

5. No Limit

Hip-hop was at its commercial (if not critical) peak in 1998, and no outfit was bigger than No Limit. Master P built an empire, free of major label backing, becoming a gazillionaire in the process. His albums were movies, with casts of dozens of artists: Silkk Tha Shocker, Mystikal, Lil' Romeo, Mia X, Fiend, C-Murder, just to name a few (seriously). Snoop also signed over there, briefly. Master P was putting out movies, with his signees getting screen time; each was accompanied by a requisite soundtrack album. It was synergy at its finest.

But then everything got overextended: Master P was a WCW wrestler for a little bit, and he kept trying out for NBA teams. Mystikal left for Jive and got a No. 1 album; new artists (including a very young Curren$y) weren't hitting the way they were supposed to. In 2003, the label filed for bankruptcy—No Limit had reached its credit limit.

4. Nelly

Nelly (born Cornell Haynes, Jr) single-handedly put the Midwest on the map in 2000, with the single "Country Grammar," off the album of the same name. That first single (which peaked at No. 7 on the charts), along with "E.I.," "Ride Wit Me," and "Batter Up," shot the album past 9 million records sold. His next album, Nellyville, debuted at number one and has gone over 10 times platinum, thanks to "Hot in Herre," "Air Force Ones," and "Dilemma feat. Kelly Rowland."

Nelly won Grammys, started dating Ashanti (who at the time was on fire), designed a women's jeans line, had an energy drink, and put his hometown people, The St. Lunatics, on. But as is the case for those generally used to the top, it's a long fall. Sweat and Suit still managed to debut at No. 1 and No. 2, but Brass Knuckles, and 5.0 came and went, and by nearly a decade after he ran the music world, it seemed as if Nelly lost his Pimp Juice. Today, people know Nelly as the first Flo Rida.

3. Death Row

The outfit of Death Row Records was always expanding. First, Suge Knight poached Dr. Dre and The DOC from Priority Records. That foundation allowed for the recruitment of Snoop, Warren G, Nate Dogg, The Dogg Pound, 2Pac, Daz Dillinger, Kurupt, Sam Sneed and on and on until MC Hammer was signed, long after his prime. They weren't just a label; for a time, they were the label: The Chronic, Doggystyle, All Eyez On Me...it almost feels belittling to list them all.

Death Row's downfall happened in three shifts. First, Sam Sneed was jumped in a meeting with Suge and Pac, since he had too many East Coast rappers in his "Lady Heroin" video; sensing something wrong, some (including The D.O.C.) ripped up their contracts and fled the label. After an argument over credits with 2Pac, Dr. Dre left to form Aftermath Entertainment. And then Tupac got murdered. No longer wanting to be associated with a sociopath like Suge Knight, everyone else rightfully got out of there.

2. Ja Rule

In the early 2000s, you couldn't go anywhere without hearing Ja Rule sing-rapping. The rapper born Jeffery Atkins, who at one time was spitting alongside Jay-Z and DMX, shifted lanes and just-about single-handledly took hip-hop pop, thanks to his collaborations with Ashanti, Jennifer Lopez, and Christina Milian. But it honestly wasn't the lightweight fare that took its toll on Ja, it was the emergence of his real-life enemy, 50 Cent.

50 emerged like a buzz saw in 2003, with two goals: to become the biggest artist in the world, and to destroy Ja Rule, and not necessarily in that order. Ja, who 50 blamed partly for the shooting that almost killed him, went from karaoke favorite to perpetually mocked, and never recovered artistically. He's currently serving jail time for tax evasion.

1. MC Hammer

Everyone knows this story: MC Hammer danced his way to the top of the charts, made a ton of money and then pissed it all away by attempting to employ half of Oakland while on tour. (Who would've thought that the backlash would come so quickly?) MC Hammer's brand of swishy-Pepsi-rap was no match for the gun-toting hyper-realism that soon assaulted the airwaves, so he had to change his image and sound.

In 1994, his "Pumps N a Bump" video came out, and—while Hammer was more...aggressive—he was wearing a Speedo and thrusting and yuck. Not the best way to win over hardcore fans! He dissed A Tribe Called Quest, Run–D.M.C. and Redman; his more-mainstream followers deserted him. So, he signed to Death Row Records. Once again, it read inauthentic. He wasn't even on the ropes; he was on the floor. He became a punchline for The Simpsons, a sob story on Behind the Music. He only became 'a thing' more recently once Twitter suggested that people follow him, for some indiscernable reason.