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- 1Cameron Diaz / The Smashing PumpkinsSeptember 26, 1998
- 2Kelsey Grammer / Sheryl CrowOctober 3, 1998
- 3Lucy Lawless / Elliott SmithOctober 17, 1998
- 4Ben Stiller / Alanis MorissetteOctober 24, 1998
- 5David Spade / Eagle-Eye CherryNovember 7, 1998 ยท 8.5
- 6Joan Allen / JewelNovember 14, 1998
- 7Jennifer Love Hewitt / Beastie BoysNovember 21, 1998
- 8Vince Vaughn / Lauryn HillDecember 5, 1998
- 9Alec Baldwin / Luciano PavarottiDecember 12, 1998
- 10Bill Paxton / BeckJanuary 9, 1999
- 11James Van Der Beek / EverlastJanuary 16, 1999
- 12Gwyneth Paltrow / Barenaked LadiesFebruary 6, 1999
- 13Brendan Fraser / Busta Rhymes & The RootsFebruary 13, 1999
- 14Bill Murray / Lucinda WilliamsFebruary 20, 1999
- 15Ray Romano / The CorrsMarch 13, 1999
- 16Drew Barrymore / GarbageMarch 20, 1999
- 17John Goodman / Tom Petty & the HeartbreakersApril 10, 1999
- 18Cuba Gooding Jr. / Ricky MartinMay 8, 1999
- 19Sarah Michelle Gellar / Backstreet BoysMay 15, 1999