Saturday Night Live — Season 25
20 episodesFirst aired 2 October 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.
E1Jerry Seinfeld/David Bowie
Oct 19991h 7m
Sketches include ""Ross Perot,"" ""Morning Latte,"" ""Mary Katherine Gallagher,"" ""Action 8 News Watch,"" ""Oz,"" and ""Alive or Dead?""
E2Heather Graham/Marc Anthony
Oct 19991h 7m
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.""
E3Norm MacDonald/Dr. Dre
Oct 19991h 7m
Sketches include ""Rudy Giuliani,"" ""Martha Stewart Living,"" ""Yankees History,"" ""Celebrity Jeopardy,"" ""NBC Crosstalk,"" ""Larry King,"" ""Michael Jaxon,"" and ""Inside the Actor's Studio.""
E4Dylan McDermott/Foo Fighters
Nov 19991h 7m
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.""
E5Garth Brooks
Nov 19991h 7m
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,"" ""Simma Da Na,"" and ""WXLU News.""
E6Jennifer Aniston/Sting
8.0Nov 19991h 7m
Sketches include ""Who Wants to be the President?,"" ""Pretty Living,"" ""Nick Burns,"" ""Mr. Peepers,"" ""Pokémon Parents,"" and ""Roberta.""
E7Christina Ricci/Beck
Dec 19991h 7m
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.""
E8Danny DeVito/R.E.M.
Dec 19991h 7m
Sketches include ""Tom Brokaw and Arnold Schwarzenegger,"" ""Delicious Dish,"" ""Mango,"" ""Boston Teens,"" ""The Ladies' Man,"" ""Rockette's Auditions,"" and ""Not My Baby!""
E9Jamie Foxx/Blink 182
Jan 20001h 7m
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: 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?
- E10
Freddie Prinze Jr./Macy Gray
Jan 20001h 7m
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, 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
- E11
Alan Cumming/Jennifer Lopez
Feb 20001h 7m
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 On"" (film), ""Siegfried and Roy,"" and ""Hello Dolly!."" Jennifer Lopez performed ""Waiting For Tonight"" and ""Feelin' So Good.""
E12Julianna Margulies/DMX
Feb 20001h 7m
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.""
- E13
Ben Affleck/Fiona Apple
Feb 20001h 7m
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?""
E14Joshua Jackson/N*Sync
Mar 20001h 7m
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.""
E15The Rock/AC/DC
Mar 20001h 7m
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 Goombahs,"" ""Today's Lady"", and ""Colonel Belmont's Horse Glue"" AC/DC performs ""Stiff Upper Lip"" and ""You Shook Me (All Night Long).""
E16Christopher Walken/Christina Aguilera
Apr 20001h 7m
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 Jones,"" ""The Census Taker,"" and ""Miss Greenwood Hills Beauty Pageant."" Christina Aguilera performs: ""I Turn To You"", ""At Last"", and ""What A Girl Wants"".
E17Tobey Maguire/Sisqo
Apr 20001h 7m
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 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.
E18John Goodman/Neil Young
May 20001h 7m
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 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""
E19Britney Spears
May 20001h 7m
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"", ""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""
- E20
Jackie Chan/Kid Rock
May 20001h 7m
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 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.
