Two and a Half Men / Guest Actors
The series Two and a Half Men recorded numerous guest appearances by otherwise well-known actors, some of whose roles play allusions to other series or other events. Most of the roles have actresses portraying Charlie Harper's numerous affairs. In the course of the series, however, it also happened that an actor played different roles or that a role was played by different actors.
| role | Explanation | actor | Season episode |
|---|---|---|---|
| Laura | Charlie's short-term affair | Kristin Bauer van Straten | 1.01 |
| Kate / Michelle | Charlie's short-term affair / NN | Liz Vassey | 1.05, 8.06, 8.07, 9.01 |
| Olivia Pearson | Charlie's ex-girlfriend | Krista Allen | 1.06 |
| Lisa | Charlie's ex-girlfriend | Denise Richards | 1.10, 2.09 |
| Prudence | Berta's granddaughter | Megan Fox | 1.12 |
| Freddie | Friend of Prudence | Noel Fisher | 1.12 |
| Stan | Charlie's accountant | Richard Lewis | 1.14 |
| Frankie / NN (presumably Dharma from Dharma & Greg ) | Alan's short-term affair / prospect for Charlie's house | Jenna Elfman | 1.15, 1.16 / 9.01 |
| Bill | Charlie's former affair, a man after sex reassignment | Chris O'Donnell | 1.18 |
| Liz | Judith's sister | Teri Hatcher | 1.19 |
| Laura Lang | Alan's divorce lawyer | Heather Locklear | 1.21 |
| Crystal | Laura Lang's assistant & Charlie's brief affair | Alana de la Garza | 1.21 |
| Delores Pasternak | Jake's teacher | Missi Pyle | 2.03, 7.21, 9.01 |
| Alicia Witt | 6.05 | ||
| Sherri | Charlie's affair, later Alan | Jeri Ryan | 2.05, 2.19, 9.01 |
| Daisy | Berta's sister | Camryn Manheim | 2.07 |
| Gail / Isabella | Woman in bar / affair of Charlie (Satanist) | Jodi Lyn O'Keefe | 2.11, 3.06, 7.21, 9.01 |
| Tina | Charlie's affair | Jennifer Taylor | 2.11 |
| Jamie Eckleberry | Alan's school friend , the 'Dog of Ekelville' | Paget Brewster | 2.12 |
| Dr. Michelle Thalmadge | Charlie's ex-girlfriend | Alicia Coppola | 2.17 |
| Assistant doctor | in practice | Ken Jeong | 2.17 |
| Pamela | Ex-wife of Charlie's client Eric | Lucy Lawless | 2.18 |
| Colleen | Charlie's girlfriend | Natalie Zea | 3.05 |
| Harvey | Father of rose | Martin Sheen | 3.07 |
| Margaret | Mother of Harvey | June Squibb | 3.07 |
| Norma | Charlie's neighbor | Cloris Leachman | 3.09 |
| Sandy | Friend of Alan | Josie Davis | 3.11 |
| Ginger | Friend & roommate of Mia | Jackie Debatin | 3.15 |
| Archie Baldwin | Jingle composer | Jon Lovitz | 3.17 |
| Andy | Kandi's father | Kevin Sorbo | 3.20 |
| Lydia | Charlie's girlfriend | Katherine LaNasa | 4.06, 4.10, 7.21, 9.01 |
| Naomi | Berta's daughter | Sara Rue | 4.07, 4.12 |
| Danielle Stewert | Charlie's neighbor | Brooke Shields | 4.14 |
| Beverly | Alan's Date from the online portal | Allison Janney | 4.15 |
| donna | Charlie's affair | Morgan Fairchild | 4.16 |
| Robin / Kate | Charlie's affair / Sam's girlfriend (Walden's poor alter ego ) | Brooke D'Orsay | 4.16, 10.10 - 10.13, 10.16, 11.18, 11.19 |
| Myra Lang | Herb Melnick's sister | Judy Greer | 4.19, 4.20 |
| Sophie | Daughter of Alan's gay friend Greg | Kay Panabaker | 4.21 |
| Fernando | Charlie's handyman | Enrique Iglesias | 4.23 |
| Nina / Chloe | Dinner company / affair from Charlie | Rachel Cannon | 4.09 / 4.23, 7.21 |
| Sharon | Alan's date | Janeane Garofalo | 5.02 |
| Margaret | Charlie's failed affair | Jennifer O'Dell | 5.02 |
| Linda Harris | Judge, friend of Charlie | Ming-na Wen | 5.03-06 |
| Artie | Charlie's temporary manager | Richard child | 5.08 |
| Silvia "Courtney Leopold" Fishman | Marriage fraud | Jenny McCarthy | 5.09, 5.16, 5.17, 8.10, 8.11, 8.12, 9.01, 9.04 |
| Gabrielle | Charlie's French affair | Justine Eyre | 5.10 |
| Lulu | Charlie's affair with a cold | Cerina Vincent | 5.12 |
| donna | Alan's girlfriend and girlfriend of Linda Harris | Kimberly Quinn | 5.03, 5.11 |
| Angie | Charlie's "older" girlfriend | Susan Blakely | 5.18, 5.19 |
| Tricia | Charlie's previous affair, fiancée of Angie's son Jeremy | Virginia Williams | 5.19 |
| Russel | Charlie's pharmacist | Martin Mull | 6.01, 6.18, 7.21, 8.08, 9.01, 10.12 |
| Ingrid | Blonde with red bra | Helena Mattsson | 6.03 |
| Jerome Burnett | Charlie's neighbor | Michael Clarke Duncan † | 6.09, 6.19 |
| Celeste Burnett | Jerome's daughter | Tinashe Kachingwe | 6.09, 6.19, 7.02, 7.11 |
| Donald Andrew "Andy" Patterson | Charlie's old friend | Emilio Estevez | 6.11 |
| Shelly | Melissa's mother | Carol Kane | 6.12, 6.14 |
| Janine | Waitress inviting Charlie and Jake over to her home | Emily Rose | 6.12 |
| Wanda | Charlie's affair | Diora Baird | 6.16 |
| Leonore | Judith's mother | Annie Potts | 7.03 |
| Betsy | Charlie's affair | Katy Mixon | 7.07, 7.16, 7.21 |
| Gail | Chelsea's girlfriend | Tricia Helfer | 7.08, 7.18, 9.01 |
| Marty Pepper | Evelyn's friend | Carl Reiner | 7.11, 8.10, 11.02 |
| Tom | Chelsea's father | Stacy Keach | 7.13, 7.16, 7.17, 7.22 |
| Ed | Chelsea's father's boyfriend | John Amos | 7.16, 7.17, 7.22 |
| Kendra | Charlie's nurse at the clinic | Sara Sanderson | 8.05 |
| Gretchen | Alan and Charlie's affair | Remember Hayes | 8.05 |
| Shauna | Michelle's daughter | Krista Kalmus | 8.06 |
| Charlie's buddy | Interested in Charlie's house | John Stamos | 9.01 |
| NN (presumably Greg from Dharma & Greg ) | Interested in Charlie's house | Thomas Gibson | 9.01 |
| Robin Schmidt | Walden's mother | Mimi Rogers | 9.12, 9.13, 10.02, 11.06 |
| Billy Stanhope | Walden's former business partner | Patton Oswalt | 9.18, 9.24, 10.02, 10.12, 10.14 |
| Jean McElroy | Lyndsey's mother | Georgia angel | 9.19, 9.20 |
| Charlie Harper | Ghost of Alan's late brother | Kathy Bates | 9.22 |
| Jill | Walden affair | Brit Morgan | 10.01 |
| Rachel | Walden affair | Bre Blair | 10.03 |
| Missi | Walden's old acquaintances and Jake's new girlfriend | Miley Cyrus | 04/10, 07/10 |
| Whitney | paid friend of Walden from the library | Lindsay Price | 07/10 |
| Dr. Steven Staven | Lyndsey's gynecologist and appointment | Willie Garson | 10.14 |
| Tammy | Jake's older friend | Jaime Pressly | 10.15, 10.20 |
| Ashley | Tammy's daughter | Emily Osment | 10.20 |
| Jerry | Ashley's older friend | Scott Bakula | 10.20 |
| Stacey | Date from Walden | Hilary Duff | 10.23 |
| Nicole | Walden's brief boss and affair | Odette Annable | 11.11, 11.12, 11.16 |
| Gretchen Martin | Larry's sister and Alan's affair | Kimberly Williams-Paisley | 11.16 - 11.19, 11.21, 11.22 |
| Vivian | Wanderer | Mila Kunis | 11.19 |
| Laurel | Deanna Russo | 07/12, 09/12 | |
| Lieutenant Wagner | Cop interrogating Alan and Walden about Charlie | Arnold Schwarzenegger | 12.16 |
The following guest stars embodied themselves: Steven Tyler in episodes 1.04 and 4.02, James Earl Jones in 6.11, Edward Van Halen in 7.01, ZZ Top in 7.21, Michael Bolton in 10.01, 12.02, 12.13 and 12.14 and Lynda Carter in 11.06, Christian Slater at 12.16. In episode 2.01 appeared as guests together: Sean Penn , Bobby Cooper , Elvis Costello and Harry Dean Stanton .