1. Sean Gunn
As Mick in Season 1, Episode 2 ("The Lorelais' First Day at Chilton"), Swan Man in Season 1, Episode 3 ("Kill Me Now") and, ya know, Kirk Gleason in all other appearances.
2. Alex Borstein
As Drella in Season 1, Episodes 1, 2, 3, and 4 ("Pilot", "The Lorelais' First Day at Chilton", "Kill Me Now", and "The Deer Hunters") and as Miss Celine in Season 3, Episode 21; Season 5, Episode 21 ("Here Comes the Son" and "Come Home")
3. Jill Brennan
As Mrs. Traister in Season 1, Episode 1 ("Pilot") and Carrie Duncan in Season 4, Episodes 13 and 21; Season 5, Episode 15 ("Nag Hammadi Is Where They Found the Gnostic Gospel", "Last Week Fights, This Week Tights", and "Jews and Chinese Food")
4. George Anthony Bell
As Professor Bell in Season 5, Episode 10 ("But Not As Cute As Pushkin") and a bailiff in Season 7, Episode 12 ("To Whom It May Concern")
5. Marion Ross
As Richard's mom, Lorelai "Trix" Gilmore, in Season 1, Episode 18; Season 3, Episode 10; Season 3, Episode 15; and Season 4, Episode 14 ("The Third Lorelai", "That'll Do, Pig", "Face-Off", and "The Incredible Sinking Lorelais") and cousin Marilyn in Season 4, Episode 16; and Season 5, Episode 13 ("The Reigning Lorelai" and "Wedding Bell Blues")
6. Jacqui Maxwell
As a Stars Hollow high student in Season 1, Episode 1 ("Pilot") and Tristan's girlfriend, Summer, in Season 1, Episodes 16 and 17 ("Star-Crossed Lovers and Other Strangers" and "The Breakup, Part II")
7. Joe Fria
As a waiter in Season 1, Episode 12 ("Double Date") and Joe Mastoni in Season 3, Episode 11 ("I Solemnly Swear")
8. Eileen Barnett
As Nanette in Season 1, Episode 3 ("Kill Me Now") and Mrs. Leahy in Season 3, Episode 18 ("Happy Birthday, Baby")
9. Floyd Van Buskirk
As Jed in Season 1, Episode 5 ("Cinnamon's Wake") and Henry in Season 5, Episode 2 ("A Messenger, Nothing More")
10. Samantha Shelton
As Libby in Season 2, Episode 6 ("Presenting Lorelai Gilmore") and Walker in Season 6, Episode 16 ("Bridesmaids Revisited")
11. Lance Barber
As Man at Inn in Season 2, Episode 7 ("Like Mother, Like Daughter") and Hugo in Season 7, Episode 8 ("Introducing Lorelai Planetarium")
12. Tiffany Fraser
As a hostess in Season 2, Episode 16 ("There's the Rub") and Shannon in Season 4, Episode 16 ("The Reigning Lorelai")
13. Seth MacFarlane
14. Riki Lindhome
As a Stars Hollow High student in Season 3, Episode 4 ("One's Got Class and the Other One Dyes") and Juliet in Season 5, Episode 15; Season 6, Episodes 1, 8, and 19 ("Jews and Chinese Food", "New and Improved Lorelai", "Let Me Hear Your Balalaikas Ringing Out", and "I Get a Sidekick Out of You")
15. Luciano Giancarlo
As Chic Guy in Season 4, Episode 4 ("Chicken or Beef?") and Italian waiter in Season 5, Episode 2 ("A Messenger, Nothing More")
16. And the amazing Sherilyn Fenn
As Sasha in Season 3, Episode 21 ("Here Comes the Son") and Anna Nardini in Season 6, Episodes 11, 12, 17, and 20; Season 7, Episodes 4, 9, 10, and 12 ("The Perfect Dress", "Just Like Gwen and Gavin", "I'm OK, You're OK", "Super Cool Party People", "'S Wonderful, 'S Marvelous", "Knit, People, Knit!", "Merry Fisticuffs", and "To Whom It May Concern")