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  • Anvilicious: The courtroom climax gets a bit preachy.
  • Critical Dissonance: Critics were very mixed towards the film, but audiences loved it. The film holds an audience score of 74% on Rotten Tomatoes compared to the 40% critic score. The film was also a hit at the box office, making back six times its budget.
  • Designated Villain: Deliberately invoked with Arthur Brooks. He's just doing his job - and is completely justified in doing so since Sonny lied to him - but in the context of the film he comes off as somewhat mean.
  • Ensemble Dark Horse: Nazo, to the point where he made The Cameo in Mr. Deeds.
  • Hilarious in Hindsight: Sandler as a Toll Booth man in a scene. Does that sound familiar?
  • Hollywood Pudgy: Sonny is described both by Corinne and by himself as "fat." We never see Sonny without his clothes on, and he's not likely to be in very good shape due to his sedentary lifestyle, but to call him "fat" is an exaggeration.
  • Narm Charm: In an otherwise tear-jerking moment: "But I wipe my own ass! I wipe my own ass!"
  • Retroactive Recognition: Julian is played by the Sprouse twins, more than half a decade before they rose to fame with The Suite Life of Zack & Cody.
  • Strawman Has a Point:
    • With Arthur Brooks. The social services agent who brings suit against Sonny for fraudulence and kidnapping appears to be heartless when he drags a frightened, begging Julian out of Sonny's apartment. However, he sincerely has Julian's best interests at heart and was right to bring Sonny to trial. When it appears that he is going to lose his case, instead of becoming bitter he is so moved by Sonny's testimony that he immediately takes out a cell phone and calls his own father (along with most of the rest of the cast).
    • The characters are aghast when the judge rules that Sonny is to be jailed for "kidnapping" Julian...which is more or less what he did.
  • Tear Jerker:
    • The "Sweet Child o' Mine" montage, after Sonny loses custody of Julian, along with Julian's heartbroken "I want Sonny to be my daddy!".
    • When the judge drops the hammer and says Sonny is still going to jail because it wasn't the matter if Sonny could take care of Julian, it's because he kidnapped him (By definition). It might seem mean-spirited, but the Judge clearly did enjoy the nice stories hearing of how good Julian was taken care of by Sonny, only she has to do her job and call out the fact that he did kidnapped him by impersonating his best friend (who was the father). Just the silence of everyone in the court room, you can tell this wasn't the fairy tale ending everyone hoped that Sonny would get.
  • Unintentional Period Piece:
    • Sonny mentions to Julian that McDonald's did not have breakfast items when he was Julian's age, and that he remembers the day that Egg McMuffins were first introduced. (That was in 1973 when Sonny would have been about two years older than Julian.) Now that McDonald's is marketing breakfast items all day...
    • In the penultimate scene, Nazo invites Sonny to his place, where "I've got Spice Channel." That adult pay-per-view network would later be renamed the "Fresh" Channel, while the "Spice" name now belongs to its parent company.
    • When Sonny first calls Social Services, he receives a response that they are closed for Columbus Day. As public opinion on Christopher Columbus changed over the years, many states would no longer recognize Columbus Day, or instead refer to the holiday as Indigenous People's Day.
    • Sonny's job as a toll booth attendant would be obsolete in 20+ years due to tolls being collected electronically by designated transponders (though one highway lane can be designated for cash transactions).
  • Values Resonance: Sonny's incredibly casual acceptance of two of his longtime (male) friends having fallen in love and the pair being portrayed in a loving, stable relationship throughout the film; though fairly common today, such a thing was both bold and rare for a film made in 1999 note .
    Mike: I am still weirded out seeing them kiss.
    Sonny: Why? They're gay. That's what gay guys do.
    Mike: Yeah, but they were like brothers to us in school.
    Sonny: They're still our brothers. Our very gay brothers.

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