Season 25
20 episodes · Oct 2, 1999
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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S25E1Jerry Seinfeld/David Bowie
Oct 2, 199967mSketches include ""Ross Perot,"" ""Morning Latte,"" ""Mary Katherine Gallagher,"" ""Action 8 News Watch,"" ""Oz,"" and ""Alive or Dead?""
S25E2Heather Graham/Marc Anthony
Oct 16, 199967mSketches include ""Al Gore and George W. Bush,"" ""The Zimmermans,"" ""The Ladies' Man,"" ""Hans and Franz,"" ""VH1 Net Aid,"" ""Dog Show, and ""Blair Witch Parody.""
S25E3Norm MacDonald/Dr. Dre
Oct 23, 199967mSketches include ""Rudy Giuliani,"" ""Martha Stewart Living,"" ""Yankees History,"" ""Celebrity Jeopardy,"" ""NBC Crosstalk,"" ""Larry King,"" ""Michael Jaxon,"" and ""Inside the Actor's Studio.""
S25E4Dylan McDermott/Foo Fighters
Nov 6, 199967mSketches 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.""
S25E5Garth Brooks
Nov 13, 199967mSketches 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,"" ""Simma Da Na,"" and ""WXLU News.""
S25E6Jennifer Aniston/Sting
Nov 20, 199967mSketches include ""Who Wants to be the President?,"" ""Pretty Living,"" ""Nick Burns,"" ""Mr. Peepers,"" ""Pokémon Parents,"" and ""Roberta.""
S25E7Christina Ricci/Beck
Dec 4, 199967mSketches 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.""
S25E8Danny DeVito/R.E.M.
Dec 11, 199967mSketches include ""Tom Brokaw and Arnold Schwarzenegger,"" ""Delicious Dish,"" ""Mango,"" ""Boston Teens,"" ""The Ladies' Man,"" ""Rockette's Auditions,"" and ""Not My Baby!""
- S25E9
Jamie Foxx/Blink 182
Jan 8, 200067mLive 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: Tracy Morgan and Jamie Foxx, Showtime At The Apollo, Stereotypically Jeffrey, and A Martin Luther King, Jr. Moment Blink-182 performs: All The Small Things and What's My Age Again?
- S25E10
Freddie Prinze Jr./Macy Gray
Jan 15, 200067mLive 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, Monica Lewinsky for Jenny Craig, Ugly Models, The Bad Doctor, The Sopranos, Charlie Rose, The Giffords, and Flacko And Teddy's World of Martin Luther King Day Trees Macy Gray performs: I Try and Why Didn't You Call Me
- S25E11
Alan Cumming/Jennifer Lopez
Feb 5, 200067mLive 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 On"" (film), ""Siegfried and Roy,"" and ""Hello Dolly!."" Jennifer Lopez performed ""Waiting For Tonight"" and ""Feelin' So Good.""
S25E12Julianna Margulies/DMX
Feb 12, 200067mSketches 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.""
- S25E13
Ben Affleck/Fiona Apple
Feb 19, 200067mSketches include ""Peanuts,"" ""Mango,"" ""Party,"" ""Frett's Film Forum,"" ""Fanatic,"" ""The Zimmermans,"" ""Cop Training,"" and ""Who Wants to Be Groped by an $11,000-aire?""
S25E14Joshua Jackson/N*Sync
Mar 11, 200067mSketches 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.""
S25E15The Rock/AC/DC
Mar 18, 200067mLive 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 Goombahs,"" ""Today's Lady"", and ""Colonel Belmont's Horse Glue"" AC/DC performs ""Stiff Upper Lip"" and ""You Shook Me (All Night Long).""
S25E16Christopher Walken/Christina Aguilera
Apr 8, 200067mLive 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 Jones,"" ""The Census Taker,"" and ""Miss Greenwood Hills Beauty Pageant."" Christina Aguilera performs: ""I Turn To You"", ""At Last"", and ""What A Girl Wants"".
S25E17Tobey Maguire/Sisqo
Apr 18, 200067mLive 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 and Porn Magazines"", ""The Flexible Yoga Student"", and ""West Link"" Sisqo performs: ""The Thong Song"" NBC and syndicated reruns replace Sisqo's performance with a dress rehearsal because in the live show version, Sisqo's microphone went dead.
S25E18John Goodman/Neil Young
May 6, 200067mLive 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 Funhouse: The Life of an SNL Catchphrase,"" ""Christopher Lowell Show,"" ""Rock 'N Roll Heaven,"" and ""Bloder Brothers Get Arrested."" Neil Young performs: ""Razor Love"" and ""Silver and Gold""
S25E19Britney Spears
May 13, 200067mLive 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"", ""Homeless Woodrow Meets Britney Spears"", ""The DeMarco Brothers"", ""DeAndra Wells' Comeback Tour"", and ""Uncle Jemima's Mash Liquor"" The host/musical guest sings: ""Oops...I Did It Again"" and ""Don't Let Me Be The Last To Know""
- S25E20
Jackie Chan/Kid Rock
May 20, 200067mLive 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 Real Audio--Madonna's Video Shoot"", ""The Zimmermans At The Golf Course"", ""Digging To The Center of the Earth"", ""Calgon"", and ""Legends In Concert"" Kid Rock performs: American Bad-Ass and Only God Knows Why The NBC rerun replaces the ""Zimmermans At The Golf Course"" sketch with an SNL mini-film by Adam McKay called ""The Procedure"" starring Willem Dafoe and Andy Richter.