1/3/26 O&A NYC THE MORNING FUNNIES: Clayton Bigsby, the World’s Only Black White Supremacist – Chappelle’s Show

Clayton Bigsby is a fictional character portrayed by Dave Chappelle in the series premiere of Chappelle’s Show in 2003. He is depicted as a blind, Black man living in a secluded community who, having never seen himself, mistakenly believes he is white and becomes a prominent white supremacist author.

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12/30/25 O&A NYC THE MORNING FUNNIES: Dave Gets Oprah Pregnant – Chappelle’s Show

After Oprah Winfrey calls to tell Dave Chappelle he is the father of her child, Dave immediately quits his job and begins living an outrageously extravagant lifestyle as “Oprah’s Baby Daddy”.

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2/27/25 O&A NYC THE MORNING FUNNIES: The Best Of I Know Black People – Chappelle’s Show

Dave Chappelle assembles a diverse group of contestants to find out how much they know about African-American Culture on I Know Black People. Continue reading

2/24/25 O&A NYC THE MORNING FUNNIES: History Lessons – Chappelle’s Show

Chappelle’s Show made history come alive. Dave Chappelle takes us on a journey introducing the comical side of Black History Month. Continue reading

6/7/22 O&A NYC THE MORNING FUNNIES: Dave Gets Oprah Pregnant – Chappelle’s Show

Dave quits his job at Chappelle’s Show after Oprah informs him she’s pregnant with this child. (Contains strong language.)
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9/10/19 O&A NYC THE MORNING FUNNIES: Chappelle’s Show – Celebrity Trial Jury Selection

Dave sounds off during the jury selection for a few high-profile court cases.
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5/1/19 O&A NYC THE MORNING FUNNIES: The Best of Tyrone Biggums- Chappelle’s Show

Chappelle’s Show Tyrone Biggums, our favorite Crackhead, faces his friends in an intervention, talks to kids about the wonders of drugs, hawks an energy drink called Red Balls and competes on “Fear Factor.” 
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1/10/19 O&A NYC THROWBACK THURSDAY: Chappelle’s Show – R. Kelly’s Piss on You

Chappelle’s Show wasn’t above going low-brow, and Dave’s spoof on R.Kelly’s salacious legal battle was quite the topic to take aim at (no pun intended, of course). Becoming just as famous as the song it was based on (Ignition Pt. 2), Piss On You proved that Chappelle had a pretty bad ass R. Kelly impression, and he could carry a tune too. Drip, drip drip! Continue reading