- Mr. Pickles trying to kill the fat wheelchair guy during "The Cheeseman". Who survives getting run through with a chainsaw, a pitchfork to the head and a giant fish hook through his eye. Mr. Pickles is visibly annoyed after the third time.
- Throughout "Loose Tooth", Tommy's Dad being barred from peeing until he just lets it go at the end of the episode.
- In "Foul Ball", when Tommy attempts to talk some sense into a disgraced baseball player, leading to a serious out of character moment for him.Tommy: Hey, you're Jim "Fouler" Johnson!
Jim: [tearfully] Yup, biggest failure in baseball history! But I'm moving on...!
Tommy: But before you go, I wanted to get you to sign m—
Tommy: But I—
Jim: I said shut up!
Tommy: [with voice raised and sounding genuinely annoyed] NO YOU DIDN'T, SO YOU SHUT UP!
- He then attempts to make him feel better by tossing him the foul ball he had caught from Jim earlier - he catches him off guard with the toss and throws it right into Jim's face, causing him to run off crying.
- Season 2 Episode 9, the closet-gay bullies simulate oral sex but go to lengths to disguise the act by contextualizing it as trying to unclog a water gun. Despite this, no more than 5 seconds later they are simulating full on penetration without context.
- It gets better in Season 3, where its revealed they're actually brothers...
- Sidekick Boy describing what Shovenpucker is. Even Mr. Pickles is stunned into silence.
- The ending of "Momma's Boy". Sheriff actually witnesses one of Mr. Pickles' rituals involving wolves, however the Sheriff being well... Sheriff, he doesn't notice this at all. Mr. Pickles is flabbergasted by his stupidity and immediately runs away.
Funny / Mr. Pickles