Season 1: 2003

Episode Number	Musical Guest	Sketches performed
1. 1-1	none	Mitsubishi Commercial, Popcopy, Nat King Cole, Home Stenographer,
2. 1-2	Mos Def	Pretty White Girl Sings Dave's Thoughts, HBO: Real Sex Street Interview, Dave's Educated Guess Line, Wrap It Up, Tyrone Biggums Classroom Visit
3. 1-3	Talib Kweli	QVC, Roots outtakes, Zapped, It's a Wonderful Chest
4. 1-4	Busta Rhymes	iMac commercial, Dave on Donahue, New York Boobs, Reparations 2003
5. 1-5	Fat Joe	Roca Pads, Redman Potty Fresh, Great Moments in Hookup History, Ask a Black Dude, Inside Chappelle's Show Studio, Redman's Potty Fresh reprise
6. 1-6	David Broom	Third World Girls Gone Wild, The Dave Chappelle Story, Ask a Gay Guy, The Mad Real World
7. 1-7	Killer Mike	Great Moments in Hookup History, Real Movies (The Matrix/Pretty Woman), Wu Tang Financial, Ask a Black Dude, Channel 3 News - Jedi Sex Scandal
8. 1-8	Slum Village	Real Movies (Ghost/Half Baked), Frontline: Racist Hollywood Animals, Tyrone Biggums Crack Intervention, "What Men Want"
9. 1-9	The Roots	Life Like a Video Game, Blackzilla, Two-Minute Special, The Playa Hater's Ball
10. 1-10	GZA	History's Greatest Wars, R. Kelly's "Piss On You" music videos, Ask a Black Dude, Real Movies (Deep Impact)
11. 1-11	De La Soul	Headphones, Make a Wish, Crazy Camera
12. 1-12	Black Star	Trading Spouses, O'Dweeds, And-1 Videos, NBA players

Extra Episodes

Title	Airdate	Sketches performed
The Best of Chappelle's Show Volume 1 Mixtape	April 13, 2003	Roca Pads, Wu Tang Financial, Frontline: Clayton Bigsby
The Best of Chappelle's Show Volume 2 Mixtape	July 16, 2003	More highlight sketches from Season 1

Season 2: 2004

Episode Number	Musical Guest	Sketches performed
13. 2-1	none	Samuel Jackson beer, Campaign Advertisements, Better in Slow Motion, The Racial Draft
14. 2-2	DMX	WacArnold's, Black Gallagher, The Niggar Family, Negrodamus
15. 2-3	John Mayer, Questlove, Dave Chappelle	White People Dancing, Ribs Sleep-Aid, The 3 Daves
16. 2-4	Ludacris	The Love Contract, Charlie Murphy's True Hollywood Stories - Rick James
17. 2-5	Cee-Lo	Tron Carter - special "Law & Order" episode, Tyrone Biggums - Red Balls Energy Drink, Negrodamus, Charlie Murphy's True Hollywood Stories - Prince
18. 2-6	Anthony Hamilton	A Moment in the Life of Lil Jon, If the Internet Was a Real Place, When Keeping It Real Goes Wrong
19. 2-7	Kanye West, Common	A Moment in the Life of Lil Jon, Marijuana Commercial, Mooney on Movies, The World Series of Dice, When Keeping It Real Goes Wrong
20. 2-8	Erykah Badu	I Know Black People, When Keeping It Real Goes Wrong, I Know Black People
21. 2-9	Wyclef Jean	Sales Pitches, Dave Gets Oprah Pregnant, Jury Duty
22. 2-10	Snoop Dogg, Tyrone Biggums	Making the Band, Dude's Night Out, Kneehigh Park
23. 2-11	Kanye West, Mos Def, Freeway	Greatest Misses – Haters in Time, Holla Service, A Gay World, Nelson Mandela's boot camp
24. 2-12	Talib Kweli	The Wayne Brady Show, Tyrone Biggums - Fear Factor
25. 2-13	Big Boi	First Black Man to Use a White Toilet, A Moment in the Life of Lil Jon, Black Bush

Extra Episodes

Title	Sketches performed
The Best of Chappelle's Show Season 2: Volume 1	The Niggar Family, Samuel Jackson beer, Jury Duty, The Wayne Brady Show
Music Jump-Off	Chappelle shows highlights of music-related sketches and performances some of which were previously unaired
The Best Of Chappelle's Show Season 2: Volume 2	Charlie Murphy's True Hollywood Stories - Prince, Racial Draft, White People Dancing

Season 3 ("The Lost Episodes"): 2006

Episode Number	Musical Guest	Sketches performed
26.	none	Dave has $55 million, Hip-Hop News, Dave Gets Revenge, Tupac is still alive
27.	none	Black Howard Dean, Watching TV while having sex, The real side of Gary Coleman, Stereotype Pixies/Audience Feedback
28.	none	Black Monsters, "Minorities" in the News, Dave Meets Show Business: Merchandising, Lil' Jon in Love, Dave on MTV Cribs.