Regrettably, Dave Chappelle's presence on the Comedy Central Network, home to his syndicated series Chappelle's Show, has dwindled since his unforeseen sabbatical to South Africa in 2005. During an ever-impressionable two-year run, Chappelle reached an apex akin to the Raw and Delirious years of Eddie Murphy's tenure as stand-up comedy's premier act. Much like Murphy, Chappelle thrived off personifying a gamut of celebrities via impeccable impersonation (see Prince, Rick James, Tiger Woods, R. Kelly, etc.). At his peak, Chappelle's comedic genius was rooted in racially charged satire---his multi-faceted sketches insightfully exposed various realms of society for the stereotypes it perpetuates. In all, Chappelle portrayed a slew of memorable characters that dominated every college male's Wednesday night viewing schedule. Chappelle's Show: it was racy, it was offensive, but damn, was it ever brilliant. Presented here is Chappelle at his best.
5. Tron
Rather than expose his dastardly drug dealing persona to the general public, our man Tron opted to 'plead the fif.' This character peaked by means of a beautifully contrived Law and Order parody, but not before shining in the Reparations and Mad Real World skits. Clackity-clack!
4. Tyrone Biggums
5. Tron
Rather than expose his dastardly drug dealing persona to the general public, our man Tron opted to 'plead the fif.' This character peaked by means of a beautifully contrived Law and Order parody, but not before shining in the Reparations and Mad Real World skits. Clackity-clack!
4. Tyrone Biggums
The very idea of a disgruntled black bum portraying a super hero (Will Smith in Hancock) is utterly laughable when you consider Tyrone's ability to lift a bus over his head under the influence of Red Balls. "It's cocaine in a can, baby!" Biggums sealed his fate as a top Chappelle persona through his hysterical performance on a mock episode of Fear Factor. Priceless!
3. Rick James
3. Rick James
The character that spawned a revolution. "I'm Rick James, bitch" infiltrated our lexicon the very moment it was uttered. Chappelle's rendition of Superfreak was so ludicrously outrageous, you simply had to applaud his ability to take James to an entirely new extreme. Furthermore, this was the skit that introduced Chappelle fans to the outlandish antics of one Charlie Murphy.
2. Black Bush
2. Black Bush
By means of this character, Chappelle hilariously summed up the lunacy that was the Bush administration. Black Bush is further complemented by the likes of the Black CIA, Black Tony Blair (played by the ultra-talented Jamie Foxx), and a random Cabinet member munching on some popcorn chicken. Red Rocks! YEAH, YAY!
1. Silky Johnson
1. Silky Johnson
Charlie Murphy's Buck Nasty and Ice T's Master of Ceremonies delivered minor chuckles at the Player Haters Ball, but Silky Johnson put the skit over the top, with superb cracks on Rosie O'Donnell and P Diddy, not to mention the oration of a classic acceptance speech upon winning Player Hater of the Year for calling in a bomb threat to the Special Olympics. Now that's hatred to the fullest! Hate, hate, hate, hate, hate!