The 25th season started on September 25, 1999 and ended on May 20, 2000 with 20 regular episodes plus a 25th Anniversary Special. The special looked back at the series’ highlights during its first quarter-century. The entire cast from last season returned for another year. Jimmy Fallon, Chris Parnell and Horatio Sanz were all promoted to repertory status, with the cast otherwise unchanged at the start of the season. As the season progressed, the show added two new cast members. Rachel Dratch, recruited from Chicago’s The Second City, where she was head writer Tina Fey’s comedy partner, joined the show in the episode hosted by Norm Macdonald. Towards the end of the season, Maya Rudolph of The Groundlings joined the show, starting with the episode hosted by John Goodman.
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Episode 1
Jerry Seinfeld/David Bowie
Sketches include ""Ross Perot,"" ""Morning Latte,"" ""Mary Katherine Gallagher,"" ""Action 8 News Watch,"" ""Oz,"" and ""Alive or Dead?""
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Episode 2
Heather Graham/Marc Anthony
Sketches include ""Al Gore and George W. Bush,"" ""The Zimmermans,"" ""The Ladies' Man,"" ""Hans and Franz,"" ""VH1 Net Aid,"" ""Dog Show, and ""Blair Witch Parody.""
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Episode 3
Norm MacDonald/Dr. Dre
Sketches include ""Rudy Giuliani,"" ""Martha Stewart Living,"" ""Yankees History,"" ""Celebrity Jeopardy,"" ""NBC Crosstalk,"" ""Larry King,"" ""Michael Jaxon,"" and ""Inside the Actor's Studio.""
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Episode 4
Dylan McDermott/Foo Fighters
Sketches include ""The Practice,"" ""The Jim Gray Show,"" ""Early Show,"" ""The Culps,"" ""Who Wants to Be a Millionaire?,"" ""Mango,"" ""Colette Reardon,"" ""State Lotto Drawing,"" and ""Disbelieving Mom.""
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Episode 5
Garth Brooks
Sketches include ""Gun Convention,"" ""James Bond,"" ""Hickory Farms Audio Visual Project,"" ""Tracy Morgan and Garth Brooks,"" ""Warner Lambert/America Home Products Merger,"" ""Express Flowers,"" ""Mango,"" ""Devil Can't Wrte No Love Songs,""…
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Episode 6
Jennifer Aniston/Sting
Sketches include ""Who Wants to be the President?,"" ""Pretty Living,"" ""Nick Burns,"" ""Mr. Peepers,"" ""Pokémon Parents,"" and ""Roberta.""
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Episode 7
Christina Ricci/Beck
Sketches include ""Bill Clinton,"" ""Spartan Cheerleaders,"" ""So This is Channukah,"" ""Who Wants to Eat?,"" ""Taxi Cab Confessions,"" ""Goth Talk,"" ""Sally Jesse Raphael,"" and ""Tribute to Madeline Kahn.""
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Episode 8
Danny DeVito/R.E.M.
Sketches include ""Tom Brokaw and Arnold Schwarzenegger,"" ""Delicious Dish,"" ""Mango,"" ""Boston Teens,"" ""The Ladies' Man,"" ""Rockette's Auditions,"" and ""Not My Baby!""
- Episode 9 Jamie Foxx/Blink 182 Live from New York, it's...Darrell Hammond Sketches include: Hillary's Departure, Hamburger Helper Anti-Bacterial, Puff Daddy and J.Lo in Therapy, The Prisoners, A Message From John Goodman, Nick Burns, Backstage SNL:…
- Episode 10 Freddie Prinze Jr./Macy Gray Live from New York, it's...a singing Chris Kattan Sketches include: NBC Special Report: Elian Gonzales, Colonel Belmont's Old-Fashioned Horse Glue, Who Wants To Be A Millionaire?, Boy Band Blowout 2000,…
- Episode 11 Alan Cumming/Jennifer Lopez Live From New York, it's...Chris Parnell! Sketches include: ""Breakfast in New Hampshire,"" ""Uncle Jemima's Down Home Mash Liquor,"" ""VH-1's Fried Chicken Fields Forever,"" ""The Culps,"" ""Dog Show,"" ""The Heat Is…
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Episode 12
Julianna Margulies/DMX
Sketches include ""Bill and Hillary Clinton,"" ""Regurgitating Family,"" ""E! News Daily,"" ""Simma Da Na,"" ""Crocodile Hunter,"" ""Erectile Dysfunction/Tootsie Roll Add,"" ""Jessica Simpson,"" and ""Bloder Brothers.""
- Episode 13 Ben Affleck/Fiona Apple Sketches include ""Peanuts,"" ""Mango,"" ""Party,"" ""Frett's Film Forum,"" ""Fanatic,"" ""The Zimmermans,"" ""Cop Training,"" and ""Who Wants to Be Groped by an $11,000-aire?""
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Episode 14
Joshua Jackson/N*Sync
Sketches include ""Tom Brokaw, Bernard Shaw, and Ted Koppel,"" ""Replacing Kathie Lee Gifford,"" ""Wedding Singers,"" ""7 Degrees Celcius,"" ""Frat Boys,"" ""Book Discussion,"" ""Colette Reardon,"" and ""Threesome.""
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Episode 15
The Rock/AC/DC
Live From New York, it's...Vince McMahon Sketches include ""Backstage SNL: Vince McMahon Warns the Wrestlers,"" ""The Ladies' Man,"" ""Mr. Peepers' Father,"" ""Morning Latte,"" ""Nicotrel/WWF Wrestlers Beat Up Chris Parnell,"" ""The…
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Episode 16
Christopher Walken/Christina Aguilera
Live from New York, it's...Dana Carvey (as George Bush, Sr.) Sketches include ""George Bush and Son,"" ""Behind the Music: Blue Oyster Cult,"" ""Elian Gonzalez Musical,"" ""The Continental,"" ""Thanks, Viagra,"" ""Jenny…
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Episode 17
Tobey Maguire/Sisqo
Live From New York, it's...Tobey Maguire Sketches include ""Bedtime At SNL,"" ""Celebrity Jeopardy,"" ""Nadeen At Burger Castle,"" ""Inside the Actor's Studio,"" ""The Atteburys' Tennis Lesson,"" ""Stavenhagen's Pawn Shop,"" ""Raspberry Soda…
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Episode 18
John Goodman/Neil Young
Live From New York, it's...Darrell Hammond Sketches include ""Who Want to Be a Millionaire?/Time Warner Attacks Disney,"" ""Platinum Mach 14,"" ""Wanna Be a VJ-3,"" ""Adele The Sleazy Office Flirt,"" ""TV…
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Episode 19
Britney Spears
Live From New York, it's...Ana Gasteyer Sketches include: ""A Message From Giuliani"", ""Gap Fat"", ""Morning Latte"", ""Boston Teens' Field Trip"", ""TV Funhouse: The Ambiguously Gay Duo"", ""Clinton Scandal Commemorative Plates"",…
- Episode 20 Jackie Chan/Kid Rock Live From New York, it's...Florence Henderson, Sarah Michelle Gellar, Gina Gershon, and Tim Meadows Sketches include: ""The Ladies' Man Dating Game"", ""Nick Burns"", ""The Culps"", ""TV Funhouse: Fun With Some…