| 1x01 | Jan. 22, 2003 | Ep. #101 | | 1x02 | Jan. 29, 2003 | Ep. #102 | | 1x03 | Feb. 05, 2003 | Ep. #103 | | 1x04 | Feb. 12, 2003 | Ep. #104 | | 1x05 | Feb. 19, 2003 | Ep. #105 | | 1x06 | Feb. 26, 2003 | Ep. #106 | | 1x07 | Mar. 05, 2003 | Ep. #107 | | 1x08 | Mar. 12, 2003 | Ep. #108 | | 1x09 | Mar. 19, 2003 | Ep. #109 | | 1x10 | Mar. 26, 2003 | Ep. #110 | | 1x11 | Apr. 02, 2003 | Ep. #111 | | 1x12 | Apr. 09, 2003 | Ep. #112 | | 1x13 | Apr. 16, 2003 | The Best of Chappelle's Show: Volume 1 Mixtape | | 1x14 | Jul. 16, 2003 | The Best of Chappelle's Show: Volume 2 Mixtape |
| 2x01 | Jan. 21, 2004 | Ep. #201 | | 2x02 | Jan. 28, 2004 | Ep. #202 | | 2x03 | Feb. 04, 2004 | Ep. #203 | | 2x04 | Feb. 11, 2004 | Ep. #204 | | 2x05 | Feb. 18, 2004 | Ep. #205 | | 2x06 | Feb. 25, 2004 | Ep. #206 | | 2x07 | Mar. 03, 2004 | Ep. #207 | | 2x08 | Mar. 10, 2004 | Ep. #208 | | 2x09 | Mar. 24, 2004 | Ep. #209 | | 2x10 | Mar. 25, 2004 | Ep. #210 | | 2x11 | Mar. 31, 2004 | Ep. #211 - Greatest Misses | | 2x12 | Apr. 07, 2004 | Ep. #212 | | 2x13 | Apr. 14, 2004 | Ep. #213 | | 2x14 | Apr. 21, 2004 | The Best Of Chappelle's Show Season 2 (Except for Rick James), Volume One | | 2x15 | Apr. 27, 2004 | Music Jump-Off | | 2x16 | May. 03, 2004 | The Best Of Chappelle's Show Season 2 Volume Two |
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