Is Jack Pellitt really a Cool Old Guy, 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 Hookers and Blow to fill the void left by his parenting?
Julia is generally regarded as the comic relief villain, but she could actually be considered the worst of the three bosses. Bobby wasn't evil, just selfish and irresponsible, and prior to killing Bobby, the worst thing Harken did was lead Nick on about a promotion he never intended to give him. Compared to rape, that's nothing. Not to mention, if the genders had been reversed, her actions would've been cast in a much darker light.
Did Rhonda's cheating lead to Harken being Properly Paranoid ... or did Harken's paranoia precede Rhonda's cheating, leading Rhonda to decide that if she's to be tried, convicted and sentenced for the crime then she may as well have the pleasure of actually committing it?
Evil Is Sexy: Julia is a sexual predator, who uses her position as Dale's boss to try to coerce him into having sex with her, despite knowing he's married. None of this makes her raping him while he's passed out any less repulsive.
Fridge Horror: As stated above, we find out in the sequel that Julia is sexually attracted to 14 year old boys. Considering that she's not above taking advantage of patients after gassing them, God only knows how many underage patients she's molested in the past.
Harsher in Hindsight: Hearing Kevin Spacey say "I own you, you're my bitch." sounds a lot more sinister in light of allegations that he molested an underage boy.
All of the scenes involving Julia sexually harassing and assaulting Dale, as well as everyone else's reactions to it, in light of the #MeToo movement.
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. 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.
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.
In the sequel, the gang is rather astonishingly quick to jump to criminal actions after what happened in the first film was the result of years of pent-up rage.
Jerkass Woobie: Rex in the second movie. It's obvious to everyone that his dad doesn't give a shit about him or anything besides his own bank account, and he's pretty visibly upset over this.
Harken killing Bobby because he thought he was sleeping with his wife. It's quite an accomplishment that he crosses it while also invoking the Kick the Son of a Bitch trope.
Bobby crosses it in his first scene as Kurt's boss, by expressing a willingness to kill thousands of people in Bolivia out of greed, by not paying extra to properly dispose of the chemicals.
Julia almost crosses it when she threatens to lie and tell his fiancee that he's a (false) sex offender and finally crosses it in the sequel when she rapes Dale while he's in a coma.
Rex crosses it in the sequel when he kills his father.
Bert crosses it when he calls the police even after the trio threatens to kill Rex if he does, confirming that he loves money more than his own son.
Nightmare Fuel: Harken's murder of Bobby. It's the only scene in the movie that's not Played for Laughs, 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.
What an Idiot!: Kurt and Dale full-stop, especially in the second movie. In both, the Big Bad had been given more than enough rope to hang himself, were it not for their idiotic decisions, such as letting it slip to Rex that they were recording his confession and that he was wearing bloodstained jeans. Of course, everything worked out eventually.
The Woobie: All three characters to an extent, though Dale qualifies most, as he's a nice, shy guy, who gets drugged by his boss, has to deal with Double Standard: Rape, Female on Male responses from almost every other characters, and the he has to deal with his assailant blackmailing (over a drunken mistake) to make him compliant.