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• S2.E1 ∙ Samuel Jackson Beer & Racial Draft
• S2.E2 ∙ Negrodamus & The Niggar Family
• S2.E3 ∙ White People Can't Dance & The Three Daves
• S2.E4 ∙ The Love Contract & True Hollywood Stories: Rick James
• S2.E5 ∙ True Hollywood Stories: Prince & Red Balls Energy Drink
• S2.E6 ∙ The Internet & Moment In The Life Of Lil Jon
• S2.E7 ∙ World Series Of Dice & Mooney On Movies
• S2.E8 ∙ I Know Black People & Keeping It Real Goes Wrong
• S2.E9 ∙ Oprah's Baby Daddy & Jury Duty
• S2.E10 ∙ Kneehigh Park & Making Da Band
• S2.E11 ∙ Mandela Boot Camp & The Time Haters
• S2.E12 ∙ Wayne Brady & Tyrone Biggums's Fear Factor
• S2.E13 ∙ Lil Jon On Lil Jon & Black Bush
• S2.E14 ∙ The Best of Chappelle's Show: Season 2, Volume 1
• S2.E15 ∙ Music Jump-Off
• S2.E16 ∙ The Best of Chappelle's Show: Season 2, Volume 2 (except Rick James)