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
28. Kool Keith
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
25. Boot Camp Click
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.
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
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
19. Black Sheep
18. Foxy Brown
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
14. Cypress Hill