The twenty-fifth season of Saturday Night Live (also branded Saturday Night Live 25 and SNL25), an American sketch comedy series, originally aired in the United States on NBC between October 2, 1999 and May 20, 2000.

Jimmy Fallon,^[1] Horatio Sanz, and Chris Parnell were promoted to repertory status. Rachel Dratch^[2] and Maya Rudolph^[3] joined the cast as featured players.

In July of 1999, when executive producer Lorne Michaels held auditions for the season, NBC introduced a new contract for first-year cast members, replacing the five- or six-year deals they had used in the past.^[4] The terms were established by NBC executives Scott Sassa and Garth Ancier. According to Peter Bogdanovich, the new contract came with the following terms:^[4]

• NBC can take a Saturday Night Live cast member off the show any time after their second year on the program and put them in an NBC sitcom.
• A cast member has the option of saying no to the first two shows proposed by NBC, but must accept the third deal.
• NBC dictates the length of the sitcom contract, which can run as long as six years.
• SNL Films, co-owned by Paramount Pictures, NBC and Lorne Michaels, has a three-movie option that would pay the star a set $75,000 for the first film, $150,000 for the second and $300,000 for the third, rates that used to be negotiable.
• NBC has the option of paying those same amounts to force a cast member to say no to a film deal offered to them by another studio.

The starting salary remained $5,000 per episode.^[4]

Starting this season Tina Fey is credited as the writing supervisor.^[5]

A Superstar film, based on the Mary Katherine Gallagher sketches, was released on October 8, 1999. Cast members Will Ferrell, Mark McKinney and Molly Shannon appear in the film. The film did modestly well at the box office but was panned by critics.^{[citation needed]}