Horrible Bosses/YMMV

Alternate Character Interpretation: Is Dale telling the truth about the playground being empty when he urinated there? Or is he lying just to save face when in fact there was a kid there who caught him? (In real life, exposing yourself to a minor can easily get you registered as a sex offender.)
Complete Monster: Harken, big time.
- Bobby may also count, since he's willing to lay people off and/or let them starve to death just because they inconvenience him. And dump his chemicals in foreign countries because it's cheaper.
Draco in Leather Pants: Julia. Probably because she's played by a rather sexually aggressive Jennifer Aniston.
Idiot Plot: 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. And even 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, but Kurt choose to bail on the job to have sex with Harken's wife.
Moral Event Horizon: Harken killing Bobby.
- He arguably crossed it earlier when he screwed Nick out of a hard earned promotion and said he will keep him from ever getting another if he leaves. That's not even going into how many dogs he must have kicked before the film started.
- Bobby crosses it so many times in his first scene its difficult to know where he confirmed his status as a Complete Monster.
  - Bobby's first scene in the film is when he comes out of the bathroom when his dad tells him to hurry up (and it's clear he's been doing coke in there) and all he does is act like a snarky Jerkass to his dad and Kurt. Are you actually referring to Bobby's first scene as Kurt's boss? If so, then I agree with you about him crossing the Moral Event Horizon several times over.
Nightmare Fuel: Harken's murder of Bobby. It's pretty much the only scene in the movie that's not Played for Laughs, and it's surprisingly realistic. Not entirely unexpected if you've been paying attention in the coming seconds, but still a bit of a shock when it comes.
Rewatch Bonus: If you missed it the first time, it's blatantly obvious the second time that Motherfucker Jones is up and phoning it in through the entire movie.
The Woobie: All three characters to an extent though Dale qualifies most.
- This troper always saw the three protagonists as mere Butt Monkeys, Dale perhaps moreso than the others if only because they don't seem to take his situation with his boss as seriously as their own. His status as The Millstone, as is mentioned on the main page, doesn't hurt either.