The 40 Biggest Hip-Hop Moments in Pop Culture History

19. Chappelle's Show Airs the First Lil Jon Skit

Date: February 25, 2004

The Moment: On the second season, in the sixth episode of what was quickly catching fire as the hottest comedy show of the new decade, Dave Chappelle aired a sketch of himself, as rapper-producer of the moment, Lil Jon, living a day in Lil Jon's life.

The Impact: "I'm Rick James, bitch," might've been the Chappelle's Show line that everyone knew, but for those who listened to rap, who knew Lil Jon's mannerisms by way of videos or interviews, this was the greatest of Chappelle's impersonations: comically over-exaggerated, painfully topical, and a hilariously accurate. In other words, pitch-perfect.

It lent the show further credibility with both casual and slightly more devoted hip-hop fans. With Questlove as house DJ, and acts like Kanye West, Talib Kweli, Big Boi, Common, Snoop Dogg, and Mos Def either performing tracks or acting in sketches, Chappelle was able to connect with all levels of rap fandom. More importantly, it proved that rappers could take a joke: Lil Jon later appeared on Chappelle's Show as himself, with Chappelle and Lil Jon playing Lil Jon, in what turned out to be one of the show's greatest moments.

The Upshot: 2004 turned out to be Lil Jon's most successful year, and his distinct voice and production reigned over popular rap through 2005, fading off in the mid-to-late aughts. The second season of Chappelle's Show became one of the most critically-acclaimed bodies of work in comedy, but Chappelle later walked away from a $50 million dollar deal while taping the third season, citing a spiritual, psychological, and philosophical burnout.

Over seven years later, and Chappelle's still only doing standup routines here and there, as the world waits for his great return. Lil Jon's still releasing music with popular acts, though he's not as prolific as he once was. He did, however, return to TV on The Celebrity Apprentice, making it all the way to the show's Final Four before losing.

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