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• S1.E1 ∙ Popcopy & Clayton Bigsby
• S1.E2 ∙ Tyrone Biggums At School & Wrap It Up Box
• S1.E3 ∙ Zapped & It's A Wonderful Chest
• S1.E4 ∙ Reparations & NY Boobs
• S1.E5 ∙ Great Moments In Hookup History & Ask A Black Dude
• S1.E6 ∙ Mad Real World & Ask A Gay Dude
• S1.E7 ∙ Real Movies & Wu-Tang Financial
• S1.E8 ∙ Tyrone Biggums's Intervention & Racist Hollywood Animals
• S1.E9 ∙ Blackzilla & Playa Haters' Ball
• S1.E10 ∙ Piss On You & The World's Greatest Wars
• S1.E11 ∙ Make-A-Wish & Fisticuff
• S1.E12 ∙ O'Dweeds & Trading Spouses
• S1.E13 ∙ The Best of Chappelle's Show: Volume 1 Mixtape
• S1.E14 ∙ The Best of Chappelle's Show: Volume 2 Mixtape