Saturday Night Live: Season 25
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.
Season 25 Lore Primer
Key plot threads, lore context, and character stakes you need to remember before diving into this season.
- Directly follows the overarching narrative developments of Saturday Night Live Season 24.
- Faction dynamics and core character alliances shift under escalating external stakes.
- Crucial mysteries introduced previously reach key turning points and narrative reckonings.
- Sets up serialized story arcs that build directly toward the climactic season finale.
Season overview
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.
Episode Guide
Season 25 Progress Shield
Jerry Seinfeld/David Bowie
Oct 2, 1999 · 67 min
Sketches include ""Ross Perot,"" ""Morning Latte,"" ""Mary Katherine Gallagher,"" ""Action 8 News Watch,"" ""Oz,"" and ""Alive or Dead?""
Heather Graham/Marc Anthony
Oct 16, 1999 · 67 min
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.""
Norm MacDonald/Dr. Dre
Oct 23, 1999 · 67 min
Sketches include ""Rudy Giuliani,"" ""Martha Stewart Living,"" ""Yankees History,"" ""Celebrity Jeopardy,"" ""NBC Crosstalk,"" ""Larry King,"" ""Michael Jaxon,"" and ""Inside the A
Dylan McDermott/Foo Fighters
Nov 6, 1999 · 67 min
Sketches include ""The Practice,"" ""The Jim Gray Show,"" ""Early Show,"" ""The Culps,"" ""Who Wants to Be a Millionaire?,"" ""Mango,"" ""Colette Reardon,"" ""State Lotto Drawing,"
Garth Brooks
Nov 13, 1999 · 67 min
Sketches include ""Gun Convention,"" ""James Bond,"" ""Hickory Farms Audio Visual Project,"" ""Tracy Morgan and Garth Brooks,"" ""Warner Lambert/America Home Products Merger,"" ""E
Jennifer Aniston/Sting
Nov 20, 1999 · 67 min
Sketches include ""Who Wants to be the President?,"" ""Pretty Living,"" ""Nick Burns,"" ""Mr. Peepers,"" ""Pokémon Parents,"" and ""Roberta.""
Christina Ricci/Beck
Dec 4, 1999 · 67 min
Sketches include ""Bill Clinton,"" ""Spartan Cheerleaders,"" ""So This is Channukah,"" ""Who Wants to Eat?,"" ""Taxi Cab Confessions,"" ""Goth Talk,"" ""Sally Jesse Raphael,"" and
Danny DeVito/R.E.M.
Dec 11, 1999 · 67 min
Sketches include ""Tom Brokaw and Arnold Schwarzenegger,"" ""Delicious Dish,"" ""Mango,"" ""Boston Teens,"" ""The Ladies' Man,"" ""Rockette's Auditions,"" and ""Not My Baby!""
Jamie Foxx/Blink 182
Jan 8, 2000 · 67 min
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 Jo
Freddie Prinze Jr./Macy Gray
Jan 15, 2000 · 67 min
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?,
Alan Cumming/Jennifer Lopez
Feb 5, 2000 · 67 min
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,"" ""Th
Julianna Margulies/DMX
Feb 12, 2000 · 67 min
Sketches include ""Bill and Hillary Clinton,"" ""Regurgitating Family,"" ""E! News Daily,"" ""Simma Da Na,"" ""Crocodile Hunter,"" ""Erectile Dysfunction/Tootsie Roll Add,"" ""Jess
Ben Affleck/Fiona Apple
Feb 19, 2000 · 67 min
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?""
Joshua Jackson/N*Sync
Mar 11, 2000 · 67 min
Sketches include ""Tom Brokaw, Bernard Shaw, and Ted Koppel,"" ""Replacing Kathie Lee Gifford,"" ""Wedding Singers,"" ""7 Degrees Celcius,"" ""Frat Boys,"" ""Book Discussion,"" ""C
The Rock/AC/DC
Mar 18, 2000 · 67 min
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,"" ""
Christopher Walken/Christina Aguilera
Apr 8, 2000 · 67 min
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 Co
Tobey Maguire/Sisqo
Apr 18, 2000 · 67 min
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'
John Goodman/Neil Young
May 6, 2000 · 67 min
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 Sl
Britney Spears
May 13, 2000 · 67 min
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
Jackie Chan/Kid Rock
May 20, 2000 · 67 min
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"