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| Saturday Night Live Season 25 : |
| Saturday Night Live aired its twenty-fifth season during the 1999-2000 television season on NBC. 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 1 - [Jerry Seinfeld David Bowie] |
| Details : Sketches include Ross Perot Morning Latte Mary Katherine Gallagher Action 8 News Watch Oz and Alive or Dead? |
| Guest Cast and Crew : David Bowie as Himself | Harold Perrineau | Jerry Seinfeld as Himself - Host | A.J. Benza | |
| Air Date : Oct. 02, 1999 |
| Episode 2 - [Heather Graham Marc Anthony] |
| Details : 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. |
| Guest Cast and Crew : Marc Anthony | Heather Graham | |
| Air Date : Oct. 16, 1999 |
| Episode 3 - [Norm Macdonald Dr] |
| Details : Sketches include Rudy Giuliani Martha Stewart Living Yankees History Celebrity Jeopardy NBC Crosstalk Larry King Michael Jaxon and Inside the Actor's Studio. |
| Guest Cast and Crew : Dr. Dre | Savion Glover | Norm Macdonald as Himself - Various Characters | |
| Air Date : Oct. 23, 1999 |
| Episode 4 - [Dylan Mcdermott Foo Fighters] |
| Details : 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. |
| Guest Cast and Crew : Dylan McDermott | |
| Air Date : Nov. 06, 1999 |
| Episode 5 - [Garth Brooks Part 2] |
| Details : 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. |
| Guest Cast and Crew : Garth Brooks | |
| Air Date : Nov. 13, 1999 |
| Episode 6 - [Jennifer Aniston Sting] |
| Details : Sketches include Who Wants to be the President? Pretty Living Nick Burns Mr. Peepers Pokémon Parents and Roberta. |
| Guest Cast and Crew : Cheb Mami | Jennifer Aniston as Host | |
| Air Date : Nov. 20, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 7 - [Christina Ricci Beck] |
| Details : 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. |
| Guest Cast and Crew : Christina Ricci | |
| Air Date : Dec. 04, 1999 |
| Episode 8 - [Danny Devito R e m] |
| Details : Sketches include Tom Brokaw and Arnold Schwarzenegger Delicious Dish Mango Boston Teens The Ladies' Man Rockette's Auditions and Not My Baby! |
| Guest Cast and Crew : Danny DeVito as Himself - Host | |
| Air Date : Dec. 11, 1999 |
| Episode 9 - [Jamie Foxx Blink 182] |
| Details : 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? |
| Guest Cast and Crew : Jamie Foxx | |
| Air Date : Jan. 08, 2000 |
| Episode 10 - [Freddie Prinze Jr Macy Gray] |
| Details : 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 |
| Air Date : Jan. 15, 2000 |
| Episode 11 - [Alan Cumming Jennifer Lopez] |
| Details : 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. |
| Guest Cast and Crew : Alan Cumming | |
| Air Date : Feb. 05, 2000 |
| Episode 12 - [Julianna Margulies Dmx] |
| Details : 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. |
| Guest Cast and Crew : DMX | Noah Wyle | Julianna Margulies | |
| Air Date : Feb. 12, 2000 |
| Episode 13 - [Ben Affleck Fiona Apple] |
| Details : Sketches include Peanuts Mango Party Frett's Film Forum Fanatic The Zimmermans Cop Training and Who Wants to Be Groped by an $11000-aire? |
| Guest Cast and Crew : Fiona Apple | Ben Affleck as Host | |
| Air Date : Feb. 19, 2000 |
| Episode 14 - [Joshua Jackson N-sync] |
| Details : 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. |
| Guest Cast and Crew : Joshua Jackson | |
| Air Date : Mar. 11, 2000 |
| Episode 15 - [The Rock Ac Dc] |
| Details : 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). |
| Guest Cast and Crew : Paul Michael Lévesque | Paul Wight | Vince McMahon | |
| Air Date : Mar. 18, 2000 |
| Episode 16 - [Christopher Walken Christina Aguilera] |
| Details : 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. |
| Guest Cast and Crew : Christopher Walken as Himself - Host | |
| Air Date : Apr. 08, 2000 |
| Episode 17 - [Tobey Maguire Sisqo] |
| Details : 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. |
| Guest Cast and Crew : Tobey Maguire | Steve Buscemi | Sisqó | Clarence Gatemouth Brown | |
| Air Date : Apr. 18, 2000 |
| Episode 18 - [John Goodman Neil Young] |
| Details : 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 |
| Guest Cast and Crew : John Goodman | |
| Air Date : May. 06, 2000 |
| Episode 19 - [Britney Spears Part 1] |
| Details : 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 |
| Guest Cast and Crew : Britney Spears as Host / Musical Guest | |
| Air Date : May. 13, 2000 |
| Episode 20 - [Jackie Chan Kid Rock] |
| Details : 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. |
| Guest Cast and Crew : Trey Anastasio | Kid Rock | Joe C. | |
| Air Date : May. 20, 2000 |