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  • Aluminum Christmas Trees: Sans the movies, which are all fake, all of George's old standup and home movie footage are real footage of Adam Sandler, some of which was shot when he and Judd Apatow were living together.
  • Base-Breaking Character:
    • Clark. He's either the funniest or least likable character in the movie. Being loosely based on Tom Buchanan doesn't help his case.
    • George himself. Either he's a relatable Jerkass Woobie, or an unlikable Jerkass. There is also another camp who found him sympathetic in the first half, only for him to lose his sympathy during the second half.
  • Broken Base: As stated below, some viewers found this movie too prolonged, while others found the movie interesting with Adam Sandler's genuinely dramatic performance.
  • Ending Fatigue: After the Halfway Plot Switch, the film continues to go on and on after all is said and done. Lead character faces death with dignity, defies odds and survives, wins over the love of his life, then there's a shipping of that woman with her husband for the sake of the children, and then the lead character and his assistant reconcile. All of these reversals are somehow part of the same story.
  • Harsher in Hindsight: After George Simmons gives a depressing self-pitying stand-up routine Ira has to follow up and does so by making fun of George. At one point he jokingly says that George's act will be followed up by Robin Williams killing himself on stage. Well, it wasn't on stage, but...
  • He Really Can Act: Adam Sandler gives a great dramatic performance.
  • Hilarious in Hindsight:
  • It Was His Sled: The second half of the movie is a romantic drama that has nothing to do with the first.
  • Jerkass Woobie: George is self-absorbed, but he is currently dying from a serious disease and tries to get his original life back together. You can see the look on his face after realizing how poorly he treated Ira.
  • Moment of Awesome: Ira giving George the speech he deserves.
  • One-Scene Wonder:
  • Padding: The film pads its near 150 minute run time with many celebrity cameos and an additional thirty-minute subplot after the main revelation that George's cancer has gone into remission. Supposedly, the film's extended versions are even worse. It's not even the storyline mentioned above that's the most annoying part, that actually makes some sense, it's several useless storylines — namely the entire subplot involving Laura as well as Mark's sitcom career — and scenes (the celebrity cameo festival in the middle film would have been a deleted scene in almost ANY other movie because of how little it has to do with the plot and how long it drags on) that should have ended up on the cutting room floor. Hell, one wonders if there even was a cutting room floor.
  • Romantic Plot Tumor: The movie didn't need an hour with George and his ex and most critics agree that it brought the movie down.
  • Tough Act to Follow: After the major success of The 40-Year-Old Virgin and Knocked Up expectations were quite high for this, especially with the curiosity surrounding Adam Sandler's lead performance. Perhaps, though, for the reasons mentioned above, the film ended up being a critical disappointment and a commercial flop.
  • The Woobie: Ira has his moments. George treats him like crap and tricks him into thinking he wanted Ira to kill him.

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