| Darsteller | Rolle |
|---|---|
| Ali Wong | Olivia (12) |
| Mark Povinelli | Todd (12) |
| Jake McDorman | Rick Miller (12) |
| Lauren Lapkus | Dee Dee (12) |
| Laura Prepon | Chelsea Newman (12) |
| Lenny Clarke | Melvin Newman (9) |
| Chelsea Handler | Sloane (7) |
| Natasha Leggero | Nikki Natoli (6) |
| Austin Butler | Luke |
| Dot-Marie Jones | |
| Michael Cassidy | Jonathan |
| Mark Valley | Chris |
| Gilles Marini | Robert |
| Josh Meyers | Dr. Carl Rosen |
| Wilmer Valderrama | Tommy |
| Bennie the Cat | Assface (3) |
| Michaela Rose Haas | 8-Year-Old Chelsea (3) |
| P. J. Byrne | Elliot (2) |
| Estelle Harris | Tess (2) |
| Cheyenne Nguyen | Young Olivia |
| Kwanwu Yu | Self - Server |
| Timon Kyle | Fireman Mike |
| Karan Soni | Stan |
| Ryan Gaul | Matt Gunn |
| Nate Torrence | Captain Steve |
| Tom Parker | Dr. Ben Thomas |
| Diana Danger | Inmate |
| Ali Williams | Bar Redhead |
| Cindy Clark | High School Lover |
| Chris Alvarado | Brian |
| Herschel Savage | |
| Harvey Joel Cohen | Guard |
| Jane Morris | Nun |
| Kevin Oestenstad | Danny the Stripper |
| Kyra Schwartz | Lily |
| Justin Dray | Yankee Fan |
| Rene Gube | Judge |
| Malachi Smith | Warren |
| Andrew Daly | Marty Mills |
| Whitney Rhea | Hostess |
| Amanda Sackett | Donna |
| Ryan Stiles | Jerry |
| Brie Bernstein | Girl |
| Shane Jenek | Maxine |
| Michael Steck | Tiffany |
| Kerri Kenney | |
| Mario Lopez | |
| Jai Rodriguez | Sandy / Chuck |
| Nat Faxon | Tim Kornick |
| Joe Wengert | Doctor |