- Actor-Inspired Element: Both Colin Farrell and Jamie Foxx came up with their character's look — pot-bellied with a combover, and retro clothes with a skull tattoo, respectively.
- Completely Different Title: In Germany, the film is called "Kill the boss". In Brazil, it's called "I want to kill my boss".
- Creator Backlash: 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 solely for the paycheck.
- Dueling Movies: With Tower Heist.
- Playing Against Type: Two of the three titular bosses.
- Jennifer Aniston plays a manipulative foul-mouthed nymphomaniac who sexually assaults her assistant.
- Colin Farrell as a racist, misanthropic Gonk who is intent on driving his father's company into the ground for money.
- Julie Bowen typically plays very grounded characters to contrast with the goofiness around her, while here she's just part of that goofiness.
- Only Sane Man Deadpan Snarker Bob Newhart as Nick's new boss, the "Twisted Old Fuck".
- What Could Have Been:
- Ashton Kutcher auditioned for the role of Dale.
- Jeff Bridges, Tom Cruise, and Philip Seymour Hoffman were all considered for the part of Harken.
- Sarah Jessica Parker and Naomi Watts were considered for Julia.
- Paul Rudd, Dax Shepard, Vince Vaughn and Owen Wilson were considered for roles.
- Frank Oz and Brett Ratner were considered to direct. The latter turned it down in favour of Tower Heist.
- Matthew McConaughey was considered for Dean "Motherfucker" Jones.
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