| Number | Name | Air date |
|---|---|---|
| 1 | Rob Lowe/Eminem | 10/07/2000 |
| 2 | Kate Hudson/Radiohead | 10/14/2000 |
| 3 | Dana Carvey/The Wallflowers | 10/21/2000 |
| 4 | Charlize Theron/Paul Simon | 11/04/2000 |
| 5 | Calista Flockhart/Ricky Martin | 11/05/2000 |
| 6 | Tom Green/David Gray | 11/18/2000 |
| 7 | Val Kilmer/U2 | 12/09/2000 |
| 8 | Lucy Liu/Jay-Z | 12/16/2000 |
| 9 | Charlie Sheen/Nelly Furtado | 01/13/2001 |
| 10 | Mena Suvari/Lenny Kravitz | 01/20/2001 |
| 11 | Jennifer Lopez | 02/10/2001 |
| 12 | Sean Hayes/Shaggy | 02/17/2001 |
| 13 | Katie Holmes/Dave Matthews Band | 02/24/2001 |
| 14 | Conan O'Brien/Don Henley | 03/10/2001 |
| 15 | Julia Stiles/Aerosmith | 03/17/2001 |
| 16 | Alec Baldwin/Coldplay | 04/07/2001 |
| 17 | Renee Zellweger/Eve | 04/14/2001 |
| 18 | Pierce Brosnan/Destiny's Child | 05/05/2001 |
| 19 | Lara Flynn Boyle/Bon Jovi | 05/12/2001 |
| 20 | Christopher Walken/Weezer | 05/19/2001 |
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