* ActorInspiredElement: Both Creator/ColinFarrell and Creator/JamieFoxx came up with their character's look -- pot-bellied with a combover, and retro clothes with a skull tattoo, respectively.
* CompletelyDifferentTitle: In Germany, the film is called "Kill the boss". In Brazil, it's called "I want to kill my boss".
* CreatorBacklash: Downplayed with Jason Bateman. While he enjoyed making the films, he admitted he didn't think the sequel was necessary and that he and the rest of the cast signed on [[MoneyDearBoy solely for the paycheck]].
* DuelingMovies: With ''Film/TowerHeist''.
* PlayingAgainstType: Two of the three titular bosses.
** Creator/JenniferAniston plays a manipulative foul-mouthed nymphomaniac who sexually assaults her assistant.
** Colin Farrell as a racist, misanthropic {{Gonk}} who is intent on driving [[CoolOldGuy his father's]] company into the ground for money.
** Creator/JulieBowen typically plays very grounded characters to contrast with the goofiness around her, while here she's just part of that goofiness.
** OnlySaneMan DeadpanSnarker Creator/BobNewhart as Nick's new boss, the "Twisted Old Fuck".
* WhatCouldHaveBeen:
** Creator/AshtonKutcher auditioned for the role of Dale.
** Creator/JeffBridges, Creator/TomCruise, and Creator/PhilipSeymourHoffman were all considered for the part of Harken.
** Creator/SarahJessicaParker and Creator/NaomiWatts were considered for Julia.
** Creator/PaulRudd, Creator/DaxShepard, Creator/VinceVaughn and Creator/OwenWilson were considered for roles.
** Creator/FrankOz and Creator/BrettRatner were considered to direct. The latter turned it down in favour of ''Film/TowerHeist''.
** Creator/MatthewMcConaughey was considered for Dean "Motherfucker" Jones.

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