- Designated Hero: We're supposed to root for Shecky in his quest to become a comedian, despite every indication that he has no talent for it whatsoever.
- Designated Villain: While he's certainly a jerkass, the worst thing that Dickie actually does during the movie is punch out Shecky under the mistaken impression that he's trying to hit on Miss Australia. On top of that, some actually find his jokes kind of amusing in a "so over-the-top vulgar it's hilarious" way, as opposed to Shecky's flat-out awful jokes.
- Hilarious in Hindsight: Shecky's outrage at Dickie's shock humor becomes this when you consider that much of Adam Sandler's own later material would make everything that Dickie says and does in this movie look downright tame.
- Nightmare Fuel: At the end of Shecky's bad dream when Dickie turns into a crude animation, and proceeds to tear out his own eyes.
- Special Effect Failure: That gun Shecky uses to shoot Dickie in one scene. Man, that gun. It looks more like a toy accompanied by a cheesy-sounding gunshot effect.
- Took the Bad Film Seriously: Billy Bob Thornton seems to be the only actor trying to play a real person, with everyone else either hamming it up as much as possible or stumbling along and trying to improvise.
YMMV / Going Overboard