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| Adam Sandler | George Simmons |
| Seth Rogen | Ira |
| Leslie Mann | Laura |
| Eric Bana | Clarke |
| Jonah Hill | Leo |
| Jason Schwartzman | Mark |
| Aubrey Plaza | Daisy |
| Maude Apatow | Mable |
| Iris Apatow | Ingrid |
| RZA | Chuck |
| Aziz Ansari | Randy |
| Torsten Voges | Dr. Lars |
| Allan Wasserman | Dr. Stevens |
| Nydia McFadden | Mandy |
Recently learning that he has a fatal disease, comic George Simmons spots a struggling performer named Ira and decides to become his mentor. The men become close friends as George teaches Ira the art of stand-up comedy, and Ira helps George define his legacy. When an old flame reappears and the disease goes into remission, George gets a chance to re-evaluate his life and figure out what is truly important to him.
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