Episodes
| Number | Name | Air date |
|---|---|---|
| 1 | Jerry Seinfeld/David Bowie | 10/02/1999 |
| 2 | Heather Graham/Marc Anthony | 10/16/1999 |
| 3 | Norm MacDonald/Dr. Dre | 10/23/1999 |
| 4 | Dylan McDermott/Foo Fighters | 11/06/1999 |
| 5 | Garth Brooks | 11/13/1999 |
| 6 | Jennifer Aniston/Sting | 11/20/1999 |
| 7 | Christina Ricci/Beck | 12/04/1999 |
| 8 | Danny DeVito/R.E.M. | 12/11/1999 |
| 9 | Jamie Foxx/Blink 182 | 01/08/2000 |
| 10 | Freddie Prinze Jr./Macy Gray | 01/15/2000 |
| 11 | Alan Cumming/Jennifer Lopez | 02/05/2000 |
| 12 | Julianna Margulies/DMX | 02/12/2000 |
| 13 | Ben Affleck/Fiona Apple | 02/19/2000 |
| 14 | Joshua Jackson/N*Sync | 03/11/2000 |
| 15 | The Rock/AC/DC | 03/18/2000 |
| 16 | Christopher Walken/Christina Aguilera | 04/08/2000 |
| 17 | Tobey Maguire/Sisqo | 04/18/2000 |
| 18 | John Goodman/Neil Young | 05/06/2000 |
| 19 | Britney Spears | 05/13/2000 |
| 20 | Jackie Chan/Kid Rock | 05/20/2000 |
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