Season 1
S1.E1 ∙ Popcopy & Clayton BigsbyS1.E2 ∙ Tyrone Biggums At School & Wrap It Up BoxS1.E3 ∙ Zapped & It's A Wonderful ChestS1.E4 ∙ Reparations & NY BoobsS1.E5 ∙ Great Moments In Hookup History & Ask A Black DudeS1.E6 ∙ Mad Real World & Ask A Gay DudeS1.E7 ∙ Real Movies & Wu-Tang FinancialS1.E8 ∙ Tyrone Biggums's Intervention & Racist Hollywood AnimalsS1.E9 ∙ Blackzilla & Playa Haters' BallS1.E10 ∙ Piss On You & The World's Greatest WarsS1.E11 ∙ Make-A-Wish & FisticuffS1.E12 ∙ O'Dweeds & Trading SpousesS1.E13 ∙ The Best of Chappelle's Show: Volume 1 MixtapeS1.E14 ∙ The Best of Chappelle's Show: Volume 2 Mixtape
Season 2
S2.E1 ∙ Samuel Jackson Beer & Racial DraftS2.E2 ∙ Negrodamus & The Niggar FamilyS2.E3 ∙ White People Can't Dance & The Three DavesS2.E4 ∙ The Love Contract & True Hollywood Stories: Rick JamesS2.E5 ∙ True Hollywood Stories: Prince & Red Balls Energy DrinkS2.E6 ∙ The Internet & Moment In The Life Of Lil JonS2.E7 ∙ World Series Of Dice & Mooney On MoviesS2.E8 ∙ I Know Black People & Keeping It Real Goes WrongS2.E9 ∙ Oprah's Baby Daddy & Jury DutyS2.E10 ∙ Kneehigh Park & Making Da BandS2.E11 ∙ Mandela Boot Camp & The Time HatersS2.E12 ∙ Wayne Brady & Tyrone Biggums's Fear FactorS2.E13 ∙ Lil Jon On Lil Jon & Black BushS2.E14 ∙ The Best of Chappelle's Show: Season 2, Volume 1S2.E15 ∙ Music Jump-OffS2.E16 ∙ The Best of Chappelle's Show: Season 2, Volume 2 (except Rick James)