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- OverviewOct 2, 1999-May 20, 200020 episodesEpisodes20. S25 E20 May 20, 2000
- Host: Jackie Chan. Music guest: Kid Rock.
- 19. S25 E19 May 13, 2000
- Britney Spears.
- 18. S25 E18 May 6, 2000
- Host: John Goodman. Music guest: Neil Young.
- 17. S25 E17 Apr 15, 2000
- Host Tobey Maguire; Sisqo.
- 16. S25 E16 Apr 8, 2000
- Host Christopher Walken; Christina Aguilera.
- 15. S25 E15 Mar 18, 2000
- The Rock; band AC/DC.
- 14. S25 E14 Mar 11, 2000
- Host: Joshua Jackson. Music guest: NSYNC.
- 13. S25 E13 Feb 19, 2000
- Host: Ben Affleck. Music guest: Fiona Apple.
- 12. S25 E12 Feb 12, 2000
- Host: Julianna Margulies. Music guest: DMX.
- 11. S25 E11 Feb 5, 2000
- Host Alan Cumming; musical guest Jennifer Lopez.
- 10. S25 E10 Jan 15, 2000
- Freddie Prinze Jr.; musical guest Macy Gray.
- 9. S25 E9 Jan 8, 2000
- Host Jamie Foxx; musical guests Blink 182.
- 8. S25 E8 Dec 11, 1999
- Host: actor Danny DeVito. Music guest: R.E.M.
- 7. S25 E7 Dec 4, 1999
- Host: actress Christina Ricci. Music guest: Beck.
- 6. S25 E6 Nov 20, 1999
- Host Jennifer Aniston; musical guest Sting.
- 5. S25 E5 Nov 13, 1999
- Host: Garth Brooks. Music guest: Chris Gaines (portrayed by Garth Brooks).
- 4. S25 E4 Nov 6, 1999
- Host: Dylan McDermott. Music guest: Foo Fighters.
- 3. S25 E3 Oct 23, 1999
- Host Norm Macdonald; musical guests Dr. Dre, Snoop Dogg, Eminem.
- 2. S25 E2 Oct 16, 1999
- Host Heather Graham; musical guest Marc Anthony.
- 1. S25 E1 Oct 2, 1999
- Host Jerry Seinfeld; musical guest David Bowie.
