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- 1Jerry Seinfeld / David BowieOctober 2, 1999
- 2Heather Graham / Marc AnthonyOctober 16, 1999
- 3Norm Macdonald / Dr. Dre, Snoop Dogg, and EminemOctober 23, 1999
- 4Dylan McDermott / Foo FightersNovember 6, 1999
- 5Garth BrooksNovember 13, 1999
- 6Jennifer Aniston / StingNovember 20, 1999
- 7Christina Ricci / BeckDecember 4, 1999
- 8Danny DeVito / R.E.M.December 11, 1999
- 9Jamie Foxx / Blink-182January 8, 2000 · 8.5
- 10Freddie Prinze Jr. / Macy GrayJanuary 15, 2000
- 11Alan Cumming / Jennifer LopezFebruary 5, 2000
- 12Julianna Margulies / DMXFebruary 12, 2000
- 13Ben Affleck / Fiona AppleFebruary 19, 2000
- 14Joshua Jackson / *NSYNCMarch 11, 2000
- 15The Rock / AC/DCMarch 18, 2000
- 16Christopher Walken / Christina AguileraApril 8, 2000
- 17Tobey Maguire / SisqóApril 18, 2000
- 18John Goodman / Neil YoungMay 6, 2000
- 19Britney SpearsMay 13, 2000 · 9.0
- 20Jackie Chan / Kid RockMay 20, 2000