When Andy Samberg got married, he invited Adam Sandler to the wedding. Sandler showed up as his character in this movie, outfit and all.
Eva Amurri Martino plays the younger version of her real-life mother, Susan Sarandon.
The film was originally rated NC-17 by the MPAA due to its explicit sexual content, making the film's Adam Sandler's only attempt at an NC-17 rated film. The film was later re-rated R on appeal.
The only Vanilla Ice hit, "Ice Ice Baby", was accused of plagiarizing "Under Pressure" by Queen and David Bowie. The musician makes a joke of it in the movie.
One of the rare Adam Sandler movies not to make back its budget. Shot for $70 million, it grossed $57 million worldwide.
Susan Sarandon also played Andy Samberg's mother in "Motherlover" and "3-Way (The Golden Rule)," skits recorded for Saturday Night Live (1975) by The Lonely Island (of which Samberg is a member).
The screenplay for this film was featured in the 2009 Blacklist; a list of the "most liked" unmade scripts of the year.
Todd was born while his mother was serving a jail sentence for statutory rape. Leighton Meester, who plays Todd's bride Jamie, was born while her mother was serving a jail sentence for drug smuggling.
Donny Berger is actually based on Uncle Donnie from Adam Sandler's 1999 comedy album Stan & Judy's Kid with the skit "The Psychotic Legend Of Uncle Donnie".
Susan Sarandon also played a teacher who had a relationship with an underage student on the series 30 Rock (2006).
In the baseball scene, Donny's bat has the number 5150 on it. 5150 is the name of an album by Van Halen, and two songs from it play during the movie. It was the first album fronted by Sammy Hagar, who didn't sing either song. It's also a California police term for a mentally disturbed person, a reference to Section 5150 of the California Welfare and Institutions Code.
Adam Sandler, Tim Herlihy, Robert Smigel, David Wain, and Ken Marino all did uncredited re-writes of the script.
The "Donnie Burger Story" scenes were shot on the Married with Children (1986) set from seasons nine through eleven, at Sony Pictures Studios.
This movie had the worst opening weekend gross for an Adam Sandler film, after Reign Over Me (2007).
Eva Amurri Martino, the young Mary McGarricle, played a young Helen in Dead Man Walking (1995). Susan Sarandon, the older Mary McGarricle, also played Sister Helen in Dead Man Walking (1995). Sarandon is Amurri Martino's mother.
The film's original title was "I Hate You Dad". That was later changed to "Donny's Boy" before settling on its present title.
The film was poorly received by critics, and disliked by many Adam Sandler fans, mostly due to the sexual relationship between 12-year-old Donnie and his teacher. Director Sean Anders won Hall of Shame at the 2013 Alliance of Women Film Journalists. The film came in second place for worst film at the 2013 Houston Film Critics Society Awards. It won worst film at the 2013 Oklahoma Film Critics Circle Awards. It won Razzies for Worst Actor (Adam Sandler) and Worst Screenplay, and was nominated for Worst Picture, Worst Supporting Actor (Nick Swardson and Vanilla Ice), Worst Screen Couple (Adam Sandler and either Leighton Meester, Andy Samberg, or Susan Sarandon) and Worst Screen Ensemble (the entire cast).
The beginning scene of the film is dated 1984, but you can see a student carrying an Alf lunch box. Alf wasn't on the air until 1986.
Rex Ryan plays Donny's lawyer, Jim Nance who is a New England Patriots fan and has a bobblehead of Bill Belichick on his desk. In real life, Rex's twin brother Rob was a member of Belichick's coaching staff when the Patriots won Super Bowls XXXVI (2001) and XXXVIII (2003).
When Donny first meets Jaime and he gives her the "book", she opens it, but when the camera angle changes to being behind Donny, the "book" is closed, but then changes back and the "book" is opened again.
Rex Ryan: As a big Patriots fan. In real life, he is the former head coach of the New York Jets and of the Buffalo Bills. Both the Jets and Bills are divisional rivals of the New England Patriots.