- Acclaimed Flop: While decently reviewed, the movie still fell short at the box office. As stated below, it’s mostly because of the extended running time and Halfway Plot Switch.
- Billing Displacement: Although billed prominently, Eric Bana appears only in the last third of the film.
- Box Office Bomb: Budget, $75 million. Box office, $71,585,235. Critics generally liked the film, but they called it out for its excessive length. This cemented Adam Sandler's Typecasting as a comedic actor and the only serious roles he would take after this were in independent films.
- Creator Killer: Universal chairman Marc Smuger would be out of a job a few months later due to this and other flops under his watch.
- Enforced Method Acting: Laura's youngest daughter's crash was real. On the DVD Commentary Judd Apatow chuckles at the idea that people would think the accident took a lot of pre-production planning and stunt work.
- Harpo Does Something Funny: Judd Apatow had Adam Sandler, Seth Rogen, Aubrey Plaza, and Jonah Hill write their own material for their stand-up routines. Apatow then filmed them performing that material.
- Promoted Fan Boy: Seth Rogen and Jonah Hill both idolized Adam Sandler when they were growing up.
- Real-Life Relative: Judd Apatow and Leslie Mann's daughters appear.
- Throw It In!: Clarke wasn't originally going to be Australian, but Eric Bana felt more comfortable improvising in his natural accent as he began his career as a comedian, so the character was changed accordingly.
- Uncredited Role: According to the DVD Commentary, Paul Thomas Anderson did an uncredited edit of the film. He did get a "Thank you" in the credits, however.
- What Could Have Been:
- Judd Apatow has said that if Adam Sandler had not been able to take the role as George Simmons, he would have most likely cast either Paul Rudd or Jason Bateman.
- Bill Hader was considered for Mark.
- James Taylor's cameo was originally meant for Bruce Springsteen.
- Write What You Know: The story was loosely based on Judd Apatow's early experiences as a struggling performer. Adam Sandler was actually Apatow's roommate during this time before moving to New York for Saturday Night Live.
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