Season 25
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
1 Jerry Seinfeld/David Bowie Oct 2, 1999 
2 Heather Graham/Marc Anthony Oct 16, 1999 
3 Norm MacDonald/Dr. Dre Oct 23, 1999 
4 Dylan McDermott/Foo Fighters Nov 6, 1999 
5 Garth Brooks Nov 13, 1999 
6 Jennifer Aniston/Sting Nov 20, 1999 
7 Christina Ricci/Beck Dec 4, 1999 
8 Danny DeVito/R.E.M. Dec 11, 1999 9 Jamie Foxx/Blink 182 Jan 8, 2000 10 Freddie Prinze Jr./Macy Gray Jan 15, 2000 11 Alan Cumming/Jennifer Lopez Feb 5, 2000 
12 Julianna Margulies/DMX Feb 12, 2000 13 Ben Affleck/Fiona Apple Feb 19, 2000 
14 Joshua Jackson/N*Sync Mar 11, 2000 
15 The Rock/AC/DC Mar 18, 2000 
16 Christopher Walken/Christina Aguilera Apr 8, 2000 
17 Tobey Maguire/Sisqo Apr 18, 2000 
18 John Goodman/Neil Young May 6, 2000 
19 Britney Spears May 13, 2000 20 Jackie Chan/Kid Rock May 20, 2000