Saturday Night Live - Season 25
Description: 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.
Episodes

Jerry Seinfeld/David Bowie
Aired: Oct 2, 1999
Sketches include ""Ross Perot,"" ""Morning Latte,"" ""Mary Katherine Gallagher,"...

Heather Graham/Marc Anthony
Aired: Oct 16, 1999
Sketches include ""Al Gore and George W. Bush,"" ""The Zimmermans,"" ""The Ladie...

Norm MacDonald/Dr. Dre
Aired: Oct 23, 1999
Sketches include ""Rudy Giuliani,"" ""Martha Stewart Living,"" ""Yankees History...

Dylan McDermott/Foo Fighters
Aired: Nov 6, 1999
Sketches include ""The Practice,"" ""The Jim Gray Show,"" ""Early Show,"" ""The ...

Garth Brooks
Aired: Nov 13, 1999
Sketches include ""Gun Convention,"" ""James Bond,"" ""Hickory Farms Audio Visua...

Jennifer Aniston/Sting
Aired: Nov 20, 1999
Sketches include ""Who Wants to be the President?,"" ""Pretty Living,"" ""Nick B...

Christina Ricci/Beck
Aired: Dec 4, 1999
Sketches include ""Bill Clinton,"" ""Spartan Cheerleaders,"" ""So This is Channu...

Danny DeVito/R.E.M.
Aired: Dec 11, 1999
Sketches include ""Tom Brokaw and Arnold Schwarzenegger,"" ""Delicious Dish,"" "...

Jamie Foxx/Blink 182
Aired: Jan 8, 2000
Live from New York, it's...Darrell Hammond Sketches include: Hillary's Departur...

Freddie Prinze Jr./Macy Gray
Aired: Jan 15, 2000
Live from New York, it's...a singing Chris Kattan Sketches include: NBC Special...

Alan Cumming/Jennifer Lopez
Aired: Feb 5, 2000
Live From New York, it's...Chris Parnell! Sketches include: ""Breakfast in New ...

Julianna Margulies/DMX
Aired: Feb 12, 2000
Sketches include ""Bill and Hillary Clinton,"" ""Regurgitating Family,"" ""E! Ne...

Ben Affleck/Fiona Apple
Aired: Feb 19, 2000
Sketches include ""Peanuts,"" ""Mango,"" ""Party,"" ""Frett's Film Forum,"" ""Fa...

Joshua Jackson/N*Sync
Aired: Mar 11, 2000
Sketches include ""Tom Brokaw, Bernard Shaw, and Ted Koppel,"" ""Replacing Kathi...

The Rock/AC/DC
Aired: Mar 18, 2000
Live From New York, it's...Vince McMahon Sketches include ""Backstage SNL: Vinc...

Christopher Walken/Christina Aguilera
Aired: Apr 8, 2000
Live from New York, it's...Dana Carvey (as George Bush, Sr.) Sketches include "...

Tobey Maguire/Sisqo
Aired: Apr 18, 2000
Live From New York, it's...Tobey Maguire Sketches include ""Bedtime At SNL,"" "...

John Goodman/Neil Young
Aired: May 6, 2000
Live From New York, it's...Darrell Hammond Sketches include ""Who Want to Be a ...

Britney Spears
Aired: May 13, 2000
Live From New York, it's...Ana Gasteyer Sketches include: ""A Message From Giul...

Jackie Chan/Kid Rock
Aired: May 20, 2000
Live From New York, it's...Florence Henderson, Sarah Michelle Gellar, Gina Gersh...