- Audience-Alienating Premise: Incest, statutory rape, pedophilia, parental neglect and abuse all rolled into one. The fact that it's a comedy makes it even worse.
- Ensemble Dark Horse:
- Fridge Brilliance: Chad threatens to use his "government-issued revolver" on Todd early in the film. At first, it seems like an error by the filmmakers, as the US Military hasn't issued revolvers in almost a century. Then you find out that Chad was only pretending to be a Marine.
- Hilarious in Hindsight: Leighton Meester portrays an apparently, quirky but actually a complete jerkoff of a bride-to-be that cheats on her husband-to-be with her brother and in the series finale of her show, Gossip Girl, a half-brother and sister (they share a brother) get married.
- One-Scene Wonder: Rex Ryan.
- The Scrappy: Uncle Donnie from The Psychotic Legend Of Uncle Donnie became this in the movie.
- Squick: Chances are, something in this movie will make you want to throw up or take a shower. Or throw up while taking a shower.
- Unfortunate Implications: As Nathan Rabin of ''My Year of Flops'' pointed out, Donny and McGarricle's student-teacher sexual relationship is treated like the ultimate teen fantasy, complete with Donny being cheered on by the whole school assembly when he's discovered in the act, so the implication is that sexual abuse of young boys isn't evil pedophilia, it's a blessing that every guy would (and should) want.Rabin: Imagine this scene with the genders reversed and you have easily the creepiest scene in the history of American mainstream comedy, and that includes Freddy Got Fingered.
- What an Idiot!: Ms. McGarricle's decision to have sex with Donny not only during a school assembly but backstage in the auditorium while the principal is giving a speech and crying out for everyone to hear not only reveals the inappropriate relationship, but is what also leads to her arrest and 30 year prison sentence.
- Hell, starting a sexual relationship with a minor alone was stupid. Even though Donny was a willing participant, he had neither the mental or emotional maturity to fully process and handle what was going on and could have done irreparable long term damage to his psyche.
- The Woobie: Todd.
- WTH, Casting Agency?: James Caan and Susan Sarandon, most especially.
YMMV / That's My Boy