The 10 Greatest Sidekicks in Rap History

"You're one hit away."

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Complex Original

Image via Complex Original

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rap sidekick (n.), a lesser rapper, traditionally a hypeman or junior-most crew member, whose reputation is, or was, contingent upon a more prominent hip-hop figure.

That's our definition, at least. Fonzworth Bentley and DJ Jazzy Jeff aside, the unsung heroes we're commemorating here today are the hypemen, the hook geniuses, the vocalist homies who don't quite shine on their own, and maybe they'll never go platinum, but they put on for the big homie. For instance: Ma$e may have been the Notorious B.I.G.'s understudy, but Lil' Cease was Biggie's sidekick in the truest spiritual sense. This distinction is crucial.

A junior hypeman or freelance wiseguy often yields a youthful, exuberant contrast to the big homie's otherwise impenetrable aura; see Public Enemy, see Dipset, et al. As a tribute to lil homies worldwise, we've ranked the ten greatest sidekicks in rap history. The list spans two-and-a-half decades and a million Henny-soaked memories.

10. Shyne

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The big homie: Puffy 

Sometimes, sidekicks lead the rougher path through life and fame. In Shyne's case, a relationship with Puffy and Bad Boy Records made for a promising start to rap stardom, as well as that stardom's end. Shyne's self-titled debut yielded "Bad Boyz" and "Bonnie & Shyne," the two last true hits of the Bad Boy's "Commission" era. But as a skinny approximation of the Notorious B.I.G.'s distinctly obese vocals, Shyne wasn't quite built to last. On December 27, 1999, at Shyne's album release party in midtown Manhattan, Shyne pulled a gun and fired a few shots into the air. Puffy and Jennifer Lopez sped off via limousine escort. Shyne went to prison for 10 years, was released in 2009, then Immigration had him deported to Belize. Now Shyne lives in Tel Aviv and raps like Jerry Stiller hooked to morphine and a stretcher. That's one hell of a life. —Justin Charity

9. Gunplay

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The big homie: Rick Ross

One of the most surprisingly talented sidekicks of hip-hop lore; Gunplay is delightful if unhinged and is a frequently terrifying rapper. He was Rick Ross' right-hand man before MMG, going all the way back to Ross' first few breakout singles. Gunplay's never surpassed the success of “Hustlin'” and the promise of a second Triple C's album, but now that Ross is taking a backseat to let his team drive, maybe Gunplay's got another shot at driving a Maybach of his own. —Justin Charity

8. Tony Yayo

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The big homie: 50 Cent 

They may be 50 Cent's ace boons alike, but in the history of G-Unit, Lloyd Banks and Tony Yayo aren't quite equal. Banks dropped three albums and a fistful of hits. Yayo sat in prison during the Get Rich / Beg for Mercy era, and since 2007 he's roughed a few G-Unit adversaries, including Jimmy Henchman's teenage son. Given all that turmoil and all those subsequent court dates, it's understandable that Yayo only released one album and very few features beyond G-Unit's group output. As 50 Cent's goon, however, Tony Yayo is legend. And strong arm aside, Tony's "Yayo" dance in the music video for "So Seductive" in 2005 guaranteed his spot in this hypeman hall of fame. —Justin Charity 

7. Silkk the Shocker

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The big homie: Master P

Nepotism. It explains so much of (real-life) big brother Master P's successfully puppeteering the career flourish of a rapper who never once successfully located the beat. Which isn't to say that Silkk the Shocker didn't have a few legit smashes. He elbowed his way onto "Make 'em Say Ugh," a 1997 posse clusterfuck that still knocks despite the 17 subsequent years in which I should have outgrown this furious nonsense. Most of Silkk's solo, unaccompanied output wilts in comparison to his biggest hits with Master P, Trina, Mr. Magic, and Mystikal. Silkk's both a No Limit foot solider and a No Limit hero. He's blessed. Somehow. —Justin Charity

6. Juelz Santana

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The big homie: Cam'ron

One of the best backstage tales from Roc-A-Fella's reign is Juelz's recounting the session in which he, Cam'ron, and Jay Z recorded “Oh Boy,” Cam's first platinum rap single. While Cam and Jay were darting back and forth into the booth, one after another, trying to top each other's latest verses, Juelz sat sideline and struggled to come up with just his first four bars. Luckily, Santana's aborted verse made for a patriotic, showstopper hook, setting the precedent for Juelz's indispensable run as Dipset's hypeman/hookman hybrid. His solo career stalled, but Juelz is a Dipshit for life. —Justin Charity

5. Flavor Flav

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The big homie: Chuck D

He spent much of the past decade eclipsing Chuck D's pop cultural rep, but within hip-hop proper, Flavor Flav was the revolutionary, Public Enemy's comic relief, and the very model of a hypeman. Chuck's lead vocals were a blunt instrument of intimidation; Flav's chants and shouts to the crowd were similarly distinct as a sort of dancefloor joy despite violence and revolutionary scheming. Flavor Flav made Public Enemy funky, and fun. While Flav was never destined for a solo career, less expected was his launching a wave of hip-hop casting for reality television shows following the first season of Flavor of Love in 2008. Also, briefly, Flav co-founded three different chicken & rib restaurant ventures in Las Vegas, Detroit, and Iowa. They've all failed. "I give FLAV credit," Chuck D tweeted in 2011. "I rather him sell something most people EAT why does Popeye Bojangles and The Colonel get automatic blackfolk?" —Justin Charity

4. Spliff Star

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The big homie: Busta Rhymes

Next to Flava Flav there is no better hypeman than Spliff Star. Busta's best friend brought an energy that even the rapper couldn't top. Aside from Spliff's supporting role on stage, his best work was as Busta's co-star in game-changing videos. Would a joint like “Dangerous” even be viewed as a cinematic classic if it weren't for Spliff's brilliant portrayal as the villain? And he showed his worth back in 2008 when he was arrested for doing what weed carriers do: He got bagged in Sweden when police found an uncontrolled substance in his hotel room after a Busta show. The two remain friends which goes to show that a true sidekick never gets envious and always plays his role. Salute. —Angel Diaz

3. Lil' Cease

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The big homie: Notorious B.I.G.

Cease A Leo—consigliere to the greatest rapper of all time, the Notorious B.I.G. If there was ever a sidekick whose shout-outs way exceeded his potential, it was Lil' Cease at the height of Biggie's commercial dominance. While Lil' Kim and Ma$e were junior superstars compared to B.I.G., Cease was Biggie's true sidekick. The two survived Cease's crashing their new Lumina (fresh off the lot!) into a turnpike railing, an accident which crippled Biggie's leg for three months. Big ruined then-16-year-old Cease's one chance to meet Michael Jackson because, per Cease's account, Biggie didn't trust M.J. around kids. After Biggie's death in 1997, Cease and Kim grew apart, and the original Bad Boy crew never got quite right with one another. At least concede that Cease has a classic feature under his belt, Kim's "Crush On You," which was that jam back in '96. —Justin Charity

2. Memphis Bleek

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The big homie: Jay Z

“Your time is coming," Jay promised Bleek. "You're one hit away." While Kanye West, Cam'ron, and Beanie Sigel did indeed mine those platinum singles, alas, Bleek's stardom wasn't to be. Since 2005, Bleek's taken Roc-A-Fella's terminal drama and the cooling of his solo career prospects in stride, even as Sigel lashes out, and even though Bleek and Kanye were never quite close to begin with. As Jay's thug apprentice, however, Bleek was the best friend a man could ask for. Even after Roc-A-Fella's contentious disintegration, Bleek still tours with Jay Z, and he's apparently on good terms with Freeway and Young Chris. Bleek occasionally speaks on his relationship with Jay, Kanye, Dame Dash, and Sigel, sounding nothing but magnanimous. Maybe Bleek's indeed listed in Hova's will, right next to Blue Ivy. —Justin Charity

1. Proof

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The big homie: Eminem

Unlike Bleek, Yayo, or Flav, rapper Proof was a prince of Detroit and a cypher icon of the Hip Hop Shop on Seven Mile Road. Proof was a year younger than Eminem, yet Proof's hometown clout predates Eminem's global infamy. “He pushed me to become who I am," Eminem said in 2006. "Without Proof’s guidance and encouragement there would have been a Marshall Mathers, but probably not an Eminem and certainly never a Slim Shady."

Modern Eminem is a rare veteran megastar who, Rihanna aside, does often seem unaccompanied and detached from hip-hop culture. But the Eminem of “Bad Meets Evil,” Devil's Night, and 8 Mile was just one of a humble few Detroit rappers who were putting on for their friends and their city as much as they were goofing for the sake of a national audience. Royce Da 5'9'', Obie Trice, Proof, Eminem, and D12 were Detroit's moment in the sun, though the moment was fleeting. While Royce would eventually reconcile with Eminem and establish a certain level of success with Slaughterhouse, Proof was gunned down on 8 Mile Road in April 2006, at the age of 32. Below, this old MTV footage of Proof and Em freestyling from the driver's side of the white boy's whooptie is a sort of fraternal wonder, just two best friends cracking jokes to a camera and doing what they do best. —Justin Charity

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