- Acclaimed Flop: One of Adam Sandler's best-reviewed films, yet didn't even make back its $25 million budget.
- Creator's Oddball: Besides being a more serious Adam Sandler role, its also the only Paul Thomas Anderson film that plays more like a typical studio film, and one of only three films in his filmography that can be classified as a comedy (along with Inherent Vice and Licorice Pizza).
- Playing Against Type: Hard to imagine an actor who's known for low-brow comedy is a star role in a rather serious art film.
- Playing with Character Type: Adam Sandler's character is, like always, antisocial, emotionally immature, and prone to uncontrollable fits of anger. Instead of that being a source of comedy, it leads to awkward, embarrassing situations, and the character leads a lonely, depressing life. Roger Ebert discussed this in his review of the film.
- Real-Life Relative:
- The four blond brothers who muscle Barry are played by four actual brothers.
- Barry's seven sisters are played by one actress - Mary Lynn Rajskub - and six nonprofessionals, four of whom were close relations.
- Throw It In!:
- Barry's line "Business is very food" was a typo which P.T. Anderson decided to leave in when filming.
- The effect of the camera suddenly jumping to an out-of-focus shot and then quickly refocusing came about when the steadicam being operated bumped into a table.
- What Could Have Been:
- Sean Penn was originally going to play Dean Trammell, but had to drop out.
- John C. Reilly was originally to play one of the men who come from Utah to collect the money. But Reilly thought that it was a strange role for him, considering how people would recognize him and wonder why he was not doing more. So he dropped out.
- Working Title: Punch-Drunk Knuckle Love, Just Desserts and The X-4 Project.
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