History Film / OldSchool

* BrickJoke: In the post-credit scene, Mitch's ex-girlfriend, Heidi, meets Frank at the supermarket and they have a friendly conversation. Having heard about Frank's divorce (and consoling him), she invites him to "a little get-together" the next evening--[[DramaticIrony which, considering what happened at the beginning of the film, [[APartyAlsoKnownAsAnOrgy is likely an orgy]].

* BrickJoke: In the post-credit scene, Mitch's ex-girlfriend, Heidi, meets Frank at the supermarket and they have a friendly conversation. Having heard about Frank's divorce (and consoling him), she invites him to "a little get-together" the next evening--[[DramaticIrony which, considering what happened at the beginning of the film, is likely an orgy]].

* TrustBuildingBlunder: The frat initiation has the pledges toss cinderblocks off a ledge, which are securely tied to their penises, the rope length having been precisely calculated so that it won't be dangerous. This works out for all but Weensie, who happens to throw his onto a manhole cover and gets dragged along with the block.

* TrustBuildingBlunder: The frat initiation has the pledges toss cinderblocks off a ledge, which are securely tied to their penises. This works out for all but Weensie, who happens to throw his onto a manhole cover and gets dragged along with the block.

* WoundGazelleGambit: Overlaps with PlayingTheVicitm. Dean Pritchard tells a class that Frank accosted him and they were witnesses, though he himself instigated the fight because he had the tape of him admitting to Megan Huang that he can bribe whoever he wants.

* TheDogBitesBack: Pritchard used to be teased by Mitch and his friends in high school, so he gets Mitch's new house rezoned for campus use only. He's also a dick to even the college students. He lampshades that it's a free country and he can do whatever he likes.

'''Dean Pritchard:''' Whatever!

* LoopholeAbuse: Mitch's house is designated specifically for social services and community housing, so they start a fraternity open to anyone as there's no rule that the frat has to be associated with the school. As Pritchard's assistant lampshades, they're very good at paperwork (Mitch is a lawyer and Beanie runs an electronics store, so they'd have to be).

* ComicallyMissingThePoint: During Frank's talk with his marriage councilor about how he really feels being married, he got offtrack by talking about what kind of panties a waitress was wearing.

* DisproportionateRetribution: [[spoiler:Mark (the cheating boyfriend of the main love interest) is driving over a bridge, he swerves to avoid another car, breaks through the side of the bridge, flips the car over, and lands right on top of Pritchard (the villainous dean of the college) who is fishing in the lake below. There's a small chance they might have survived that but then the car ''explodes''.]]

** Dean Pritchard harasses Mitch because he was bullied by Mitch and his friends in high school. While an understandable reason for Pritchard to give them grief, especially given the kind of bullying he was subjected to (locking him in a dumpster for extended periods), he simply can't let it go and goes to increasing lengths to sabotage them. He subverts the system by pressuring a student into revoking the so-called frat's charter by promising assistance with her Columbia Law application, while later gloating that he lied about his end of the deal, making him little better than the bullies his adversaries used to be.

* WhatTheHellHero: Beanie calls Mitch out for cussing in front of his son without giving a heads-up (see CoverInnocentEyesAndEars), because Mitch was frustrated at the moment and didn't really want to create a fraternity. Beanie says he and their friends were trying to help him after leaving his cheating ex-girlfriend, making Mitch feel guilty and reluctantly accepts.
-->'''Beanie:''' Don't say sorry to me. You let down Frank. You let down me. Most importantly, you let down Max. And right about now I'm having a hard time trying to figure out why I take time out of my schedule to help you get over... Max, can you earmuff it for me? ''(Max covers his ears)'' That whore you dated.

* PoliticallyIncorrectVillain: Dean Pritchard, if this dialogue is anything to go by.

** Dean Pritchard harasses Mitch because he was bullied by Mitch and his friends in high school. While an understandable reason for Pritchard to give them grief, especially given the kind of bullying he was subjected to (locking him in a dumpster for extended periods), he simply can't let it go and goes to increasing lengths to sabotage them. He subverts the system by pressuring a student into revoking the so-called frat's charter by promising assistance with her Columbia Law application, making him little better than the bullies his adversaries used to be.

* BrickJoke: In the post-credit scene, Mitch's ex-girlfriend, Heidi, meets Frank at the supermarket and they have a friendly conversation. After hearing about Frank's divorce, she invites him to "a little get-together" the next evening--[[DramaticIrony which, considering what happened at the beginning of the film, is likely an orgy]].

* TranquilizerDart: PlayedForLaughs. Frank accidentally shoots himself in the neck with one.

** Dean Pritchard, who harasses Mitch for no other reason than being bullied by Mitch and his friend in high school.
*** Being bullied is a great reason to exact revenge. It sounds like they were very cruel to the Dean, locking him in a dumpster for extended periods. The problem is with the way he goes about getting revenge. He subverts the system by pressuring a student into revoking the so-called frat's charter by promising assistance with her Columbia Law application. And let's not lose sight that these are middle-aged men seeking to relive their glory days "while giving nothing back to the school or the community."

* ScrewThisImOuttaHere: After finding out that it's in the bylaw that the only way to keep the fraternity is take a course of tests, Beanie decided he wants out of the fraternity. Though Mitch convince him otherwise.

* BrickJoke: In the post-credit scene, Mitch's ex-girlfriend, Heidi, meets Frank at the supermarket and they have a friendly conversation. After hearing about Frank's divorce, she invites him to "a little get-together" the next evening--which, considering what happened at the beginning of the film, is likely an orgy.