- Acclaimed Flop: Currently Adam Sandler's second best reviewed film (beaten in 2017 by The Meyerowitz Stories and later Uncut Gems), yet didn't even make back it's $25 million budget
- Playing Against Type: Hard to imagine an actor who's known for low-brow comedy is a star role in a rather serious 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.
Trivia / Punch-Drunk Love