A successful comedian with a terminal condition spends the twilight of his existence mentoring a comparatively inexperienced entertainer.
| Adam Sandler | ... George Simmons |
| Seth Rogen | ... Ira Wright |
| Leslie Mann | ... Laura |
|
| Eric Bana | ... Clarke |
| Jonah Hill | ... Leo Koenig |
| Jason Schwartzman | ... Mark Taylor Jackson |
| Aubrey Plaza | ... Daisy Danby |
| The RZA | ... Chuck |
|
| Iris Apatow | ... Ingrid |
| Maude Apatow | ... Mable |
|
| Aziz Ansari | ... Randy |
| Torsten Voges | ... Dr. Lars |
| Allan Wasserman | ... Dr. Stevens |
| Rod Man | ... Himself |
| Wayne Federman | ... Comedy & Magic Manager |
| Mike O'Connell | ... MySpace Escort |
| James Taylor | ... Himself |
| Nicole Parker | ... Dawn |
| Nydia McFadden | ... Mandy |
| Andy Dick | ... Himself |
| Charles Fleischer | ... Himself |
| Nicol Paone | ... George's Sister |
| George Coe | ... George's Dad |
| Budd Friedman | ... Himself |
| Monty Hoffman | ... Himself |
| Carol Leifer | ... Herself |
| Paul Reiser | ... Himself |
| Mark Schiff | ... Himself |
| George Wallace | ... Himself |
| Norm MacDonald | ... Himself |
| Dave Attell | ... Himself |
| Sarah Silverman | ... Herself |
| Bryan Batt | ... George's Agent |
| Maggie Siff | ... Rachel |
| Eminem | ... Himself |
| Ray Romano | ... Himself |
| Jon Brion | ... Jam Musician |
| Sebastian Steinberg | ... Jam Musician |
| James Gadson | ... Jam Musician |
| Arshad Aslam | ... Yo Teach Cast Member |
| Bo Burnham | ... Yo Teach Cast Member |
| M. Michelle Nishikawa | ... Yo Teach Cast Member |
| Kenny Copeland, Jr. | ... Yo Teach Cast Member |
| Calvin Sykes | ... Yo Teach Cast Member |
| Ca'Shawn Sims | ... Yo Teach Cast Member |
| Mandi Kreisher | ... Yo Teach Cast Member |
| Phillip Andre Botello | ... Yo Teach Cast Member |
| Carla Gallo | ... Miss Pruitt on Yo Teach |
| Ernest Thomas | ... Yo Teach Principal |
| Tonita Castro | ... Bonita |
| Carlos Andrade | ... Gardener |
| Steve Bannos | ... Deli Manager |
| Justin Long | ... Re-do Guy |
| Lucas Dick | ... College Guy with Camera |
| Tyler Spindel | ... College Guy with Camera |
| Deamor Yi | ... 8 Year-Old Girl Fan |
| Elaine Kao | ... Mom with Camera |
| King Kedar | ... Family with Camera |
| Andre Butler, Jr. | ... Family with Camera |
| Tanya Acker | ... Family with Camera |
| Jarrett Grode | ... Magician |
| Qiana Chase | ... Chuck's Wife |
| Tom Anderson | ... Himself |
| John Hartmann | ... Private Jet Pilot |
| Dave Rath | ... San Francisco Theatre Manager |
| Dan Harmon | ... Paparazzo at Medical Center |
| Brandon Cournoyer | ... Paparazzo at Medical Center |
| Kyle Kinane | ... Paparazzo at Medical Center |
| Mark Cohen | ... Emcee at Improv |
| Denise Meyerson | ... Deli Customer |
| Joanie Marx | ... Deli Customer |
| Adam Bernstein | ... Hot Dog-Eating Champion's Son |
| Da'Vone McDonald | ... Hot Dog-Eating Co-Star |
| Orny Adams | ... Himself |
| Al Lubel | ... Himself |
| Jerry Minor | ... Himself |
| Eleanor Zee | ... George's Mom |
| Ben Meyerson | ... George's Brother-in-Law |
| Sammy Jack | ... George's Young Nephew |
| Kim Taylor | ... James Taylor's Musician |
| Andrea Zonn | ... James Taylor's Musician |
| Kate Markowitz | ... James Taylor's Musician |
| Arnold McCuller | ... James Taylor's Musician |
| Larry Goldings | ... James Taylor's Musician |
| Luis Conte | ... James Taylor's Musician |
| Russ Kunkel | ... James Taylor's Musician |
| Jimmy Johnson | ... James Taylor's Musician |
| Brad Grunberg | ... Comedy & Magic Club Audience |
| Brian Lally | ... Comedy & Magic Club Audience |
