* AlternateCharacterInterpretation: Is Donald Sutherland really a CoolOldGuy, or a neglectful father who spent all his time building his company to the detriment of his son, who seems like a {{Jerkass}} but has actually just turned to HookersAndBlow to fill the void left by his parenting?
%%Do NOT add Complete Monster entries without going to cleanup thread first.
* DracoInLeatherPants: Julia. Probably because she's played by a rather [[PlayingAgainstType sexually aggressive]] Creator/JenniferAniston.
* IdiotPlot: Recording their conversations with their bosses right from the start would have solved a lot of the main characters' problems to varying degrees, but it takes them the entirety of the movie and a tip from a petty gangster wanna-be to figure that out. When they try it the normal way they're thwarted by their own constantly increasing stupidity.
** The ironic thing is the recording actually ''would'' have worked, [[spoiler: but Kurt choose to bail on the job to have sex with Harken's wife.]]
** And two of them already had ample evidence to convict their bosses as it is. Julia had recorded evidence of herself molesting someone under anaesthetic, and Bobby wasn't exactly being discreet about his cocaine use.
* MoralEventHorizon: [[spoiler:Harken killing Bobby.]]
** Bobby crosses it so many times in his first scene as Kurt's boss.
** Julia crosses it when she [[spoiler:threatens to lie and tell his fiancee that he's a (false) sex offender]].
* NightmareFuel: [[spoiler: Harken's murder of Bobby.]] It's the only scene in the movie that's not PlayedForLaughs, and it's surprisingly realistic. Not unexpected if you've been paying attention in the coming seconds, but still a bit of a shock when it comes.
* OneSceneWonder: [[Film/FantasticFour Ioan Gruffudd]] as a [[spoiler: male prostitute Dale mistakes for a hitman]].
** Kenny Summerfeld.
* RewatchBonus: If you missed it the first time, it's blatantly obvious the second time that [[spoiler: Motherfucker Jones is up and phoning it in through the entire movie.]]
* TheWoobie: All three characters to an extent though Dale qualifies most.