- The conversation between Crewe and the cops that pulled him over.
- Crewe getting the ultimate revenge on his girlfriend by causing her car to get totalled in a massive pileup.
Crewe: Hey, Lena! I think we should start seeing other people!
Crewe: Good news, boys, I didn't spill my beer.
- And then...
- The fact that Turley's (played by The Great Khali) accent is so thick that they have to subtitle everything he says.
"He was like OWMYBALLS!"
- Caretaker finding out he's only half-a-star (out of 5) on the Warden's rating system.
Crewe: You're about as maniacal as a boxful of kittens.
- Brucie has a number of these.
Brucie: Hey, it slipped! I just had popcorn.
- After his first attempt at a pass sails all the way over Crewe's head:
Brucie: I've got a bird. He's name's Ronnie.
- After getting pounded by Torres during practice:
Caretaker: Well, tell Ronnie you got knocked the fuck out!
Brucie: (nearly in tears) Now I'll never get to play!
- Brucie's realization that he's useless now that the black inmates have joined Crewe's team:
Caretaker: Who're we gonna crush?!Everyone: THE GUARDS!!!Caretaker: Who're we gonna kill?!Everyone: THE GUARDS!!!Caretaker: Who're we gonna kiss?(Brucie realizes his screw-up...)Caretaker: Gotcha.(Everyone gets to pissing off Brucie.)
- During the Training Montage, too. Dude never gets to catch a break:
Battle: What are you doing, Brucie can't kick worth a shit!Scarborough: I know, recover the ball!Brucie: Jesus Christ, my savior, if you promise to help me out with this one, I promise to stop cheating on my wife with black guys!
- Scarborough puts Brucie into the kickoff team to kick the ball.
- The scene in the shower where they're recruiting Battle. Hilarious because they're awkwardly trying to not look at his "hammer."
Caretaker: Let's get outta here before that thing bites someone.
Crewe: We'll see you and your pet iguana at practice.
Crewe: Battle, I think this is yours. (tosses him a massive jockstrap)
- Which leads to this:
Deacon: I still don't think that's big enough!
- Cheeseburger Eddy's Rhymes at the Basketball Court.
- Scarborough running drills with the team during the training montage. For an old man, he has no problem knocking the cons on their butts until he gets to Turley. He runs full force into the man-mountain, who doesn't budge. Scarborough pats him on the shoulder and very stiffly limps away.
- Engleheart's transition after his steroids were swapped for estrogen pills. He goes from smashing a Gatorade table at the beginning of the movie to cheering with the Con's "cheerleaders" near the end.
- Crewe's solution to a biased referee problem.
Cheeseburger: You always gotta protect the McNuggets!
- While mixed with a awesome moment, the "I think I make him shit himself" scene got some hilarity thanks to Megget and Deacon.
Megget: Yo! I'll make sure to send them books to the hospital, pimp.Deacon: And some diapers!
Baby-Face Bob: Convicts are people too, Chris. Now gimme your wallet.Chris Berman: What?Baby-Face Bob: I'm just kidding!
- The Warden "gets what's coming to him" at the end by being the victim of a Gatorade Bath.
Deacon: (after he and Battle douse the Warden) Great game, sir! (Both run off)Warden: That's a week in the hotbox!Battle: (offscreen) Who gives a shit?!
- While Crewe and Caretaker are having a moment.
Crewe: Here's to... (pause) the first friend I've had in I don't know how long.Switowski: Hey, I thought I was your friend Paul.Crewe: You are, Switowski. Just finish your coloring book and go back to sleep.Switowski: Okay.
Funny / The Longest Yard
In the Remake: