Episodes
See also: List of Saturday Night Live episodes| # | Host(s) | Musical guest(s) | Original airdate | |
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| 447 | 1 | Cameron Diaz | The Smashing Pumpkins | September 26, 1998 |
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Jonathan Richman and Tommy Larkins, who performed musical interludes in Diaz's film There's Something About Mary, made a cameo appearance after a sketch. Steve Martin and Dan Aykroyd reprise their roles as The Festrunk Brothers (a.k.a. "The Wild and Crazy Guys") during the Roxbury Guys sketch. John Goodman made a cameo appearance as Linda Tripp during the cold open. Jimmy Fallon, Horatio Sanz and Chris Parnell's first episode as cast members. The Smashing Pumpkins performed "Perfect". |
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| 448 | 2 | Kelsey Grammer | Sheryl Crow | October 3, 1998 |
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Shaquille O'Neal (who was originally chosen to be the host, but backed out) appeared in two sketches: "Big Bernard," about an overgrown man who comes home late and receives a spanking by his father (played by Tracy Morgan), and "Morning Latte" as himself. Guest appearances by Hal Linden, Christine Baranski, and Patti Lupone. Sheryl Crow performed "My Favorite Mistake". |
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| 449 | 3 | Lucy Lawless | Elliott Smith | October 17, 1998 |
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Chucky, the possessed doll from Bride of Chucky and related films, made a guest appearance on "Weekend Update." Judge Judy appeared as herself in a sketch in which she is being mocked by Cheri Oteri. Elliott Smith performed "Waltz #2." |
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| 450 | 4 | Ben Stiller | Alanis Morissette | October 24, 1998 |
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Yankee players David Cone, Chili Davis, Tino Martinez, Graeme Lloyd, and David Wells appeared in the opening monologue. Alanis Morissette performed "Thank U" and "Baba". |
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| 451 | 5 | David Spade | Eagle-Eye Cherry | November 7, 1998 |
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Brad Pitt appeared in the cold opening where David Spade visits his therapist (played by Pitt) about his overwhelming fame. Former cast member Chris Rock cameoed in a Mango sketch as an admirer of a new dancer named Kiwi (played by David Spade). Eagle-Eye Cherry performed "Save Tonight". |
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| 452 | 6 | Joan Allen | Jewel | November 14, 1998 |
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Jewel performed "Hands" and "Down So Long". John Goodman made a cameo in a Suel Forrester Sketch. |
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| 453 | 7 | Jennifer Love Hewitt | Beastie Boys | November 21, 1998 |
| Beastie Boys performed "Three MC's and One DJ" and "Sabotage". As well, Beastie Boy Adam Horovitz made a cameo appearance during the Spartan Cheerleaders sketch as Jennifer Love Hewitt's character's boyfriend. | ||||
| 454 | 8 | Vince Vaughn | Lauryn Hill | December 5, 1998 |
| Lauryn Hill performed "Doo Wop (That Thing)" and "Ex-Factor." | ||||
| 455 | 9 | Alec Baldwin | Luciano Pavarotti Vanessa Williams Philadelphia Boys Choir & Chorale |
December 12, 1998 |
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John Goodman had a cameo appearance during Baldwin's monologue and in the "Bill Brasky" sketch featuring Goodman, Will Ferrell, and Alec Baldwin as the drunken businessmen. Luciano Pavarotti and Vanessa Williams performed "Adeste Fideles." As well, Vanessa Williams appeared as a Kwanzette during Weekend Update while Tim Meadows sings a song about Kwanzaa. |
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| 456 | 10 | Bill Paxton | Beck | January 9, 1999 |
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Titanic director James Cameron had a pre-recorded cameo in a sketch parodying his film. Debbie Matenopoulos appeared as herself in a parody of The View. Beck performed "Nobody's Fault but My Own" and "Tropicalia." |
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| 457 | 11 | James Van Der Beek | Everlast | January 16, 1999 |
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Darrell Hammond imitated an absent Don Pardo as announcer, particularly in a two-part running gag where Don Pardo (Darrell Hammond) tries to seduce Van Der Beek. Everlast performed "What It's Like." |
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| 458 | 12 | Gwyneth Paltrow | Barenaked Ladies | February 6, 1999 |
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Ben Affleck cameoed in Paltrow's opening monologue. Barenaked Ladies performed "It's All Been Done." This episode was submitted for Emmy consideration for 1998-1999 season. |
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| 459 | 13 | Brendan Fraser | Busta Rhymes The Roots |
February 13, 1999 |
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Former SNL writer/featured player Tom Davis appeared in the monologue. Other cameos include George Plimpton (after the "Shut Up and Enjoy the Ozzy" sketch) and John Goodman (as Linda Tripp during the cold open). Busta Rhymes performed "Gimme Some More" and "Tear da Roof Off." |
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| 460 | 14 | Bill Murray | Lucinda Williams | February 20, 1999 |
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Former castmember (and co-star of Caddyshack) Chevy Chase appeared in the "Quotable Caddyshack" sketch to re-enact his one scene with Bill Murray. Stephanie Seymour cameoed in the cold open. Lucinda Williams performed "Can't Let Go" and "2 Kool 2 Be 4-gotten." |
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| 461 | 15 | Ray Romano | The Corrs | March 13, 1999 |
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Romano's Everybody Loves Raymond co-stars, Peter Boyle and Doris Roberts, made cameo appearances during the monologue, in which Boyle discussed his time as host in the 1970s and Roberts discussed her role in My Giant. The Corrs performed "What Can I Do?" and "So Young." |
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| 462 | 16 | Drew Barrymore | Garbage | March 20, 1999 |
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Edward Norton cameoed in a VH1 commercial parody as Daryl Dragon. Garbage performed "Special" and "When I Grow Up." |
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| 463 | 17 | John Goodman | Tom Petty & the Heartbreakers | April 10, 1999 |
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Writer and future cast member Tina Fey appears as a fake audience member interrupting the host. Tom Petty & The Heartbreakers performed "Swingin'" and "Room at the Top." |
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| 464 | 18 | Cuba Gooding, Jr. | Ricky Martin | May 8, 1999 |
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Monica Lewinsky made a special appearance in the cold open where Bill Clinton (played by Darrell Hammond) imagines life after his Presidency, and in a sketch with Tim Meadows' Ladies Man character. John Goodman makes a voice only guest appearance. Ricky Martin performed "Livin' La Vida Loca." |
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| 465 | 19 | Sarah Michelle Gellar | Backstreet Boys | May 15, 1999 |
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David Boreanaz, Howie Dorough from the Backstreet Boys, and Seth Green cameoed in the recurring sketch, "Tiger Beat's Ultra Super Duper Dreamy Love Show." Backstreet Boys performed "I Want It That Way" and "All I Have to Give." |
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