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1* AccidentalAesop: While revenge is tempting, there are better and healthier ways to go about ''getting'' someone. At the end of the first movie [[spoiler: Dale resorts to tricking Julia into committing sexual assault on camera, giving him leverage over her]]. If the protagonists chose to report or record their bosses' abusive behavior, they could've stuck it to their bosses without resorting to actions that could've gotten them sent to prison.
2* AlternateCharacterInterpretation:
3** Is Jack Pellitt 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?
4** 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 [[spoiler: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.
5** Did Rhonda's cheating lead to Harken being ProperlyParanoid ... 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 [[ThenLetMeBeEvil she may as well have the pleasure of actually committing it?]]
6%%Do NOT add Complete Monster entries without going to cleanup thread first.
7* BaseBreakingCharacter: Many viewers love Julia for averting DoubleStandardAbuseFemaleOnMale but there's some viewers who had an issue with the whole thing still being PlayedForLaughs unlike Harken and being the only of the bosses to end up being a KarmaHoudini.
8* CrossesTheLineTwice: Practically every scene with Bobby.
9-->'''Bobby''': ''(to Kurt)'' You either fire the fatty, or you fire the cripple, or I fire all three of you.
10* {{Designated Hero}}es: The three protagonists frequently act like criminals and commit minor actions that snowball into a huge disaster, but the audience still cheers them on. Justified as this is helped by the fact that their bosses are ''significantly'' worse and many of their bad decisions are them lashing out at their mistreatment.
11* DracoInLeatherPants: Julia. Probably because she's played by a rather [[PlayingAgainstType sexually aggressive]] Creator/JenniferAniston.
12* FridgeHorror: [[Fridge/HorribleBosses See here]].
13* HarsherInHindsight:
14** Hearing Creator/KevinSpacey say ''"I own you, you're my bitch."'' sounds a lot more sinister in light of allegations that he molested an underage boy.
15** 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.
16* HilariousInHindsight: At one point, Julia tells Dale she's [[spoiler: a "squirter"]]. Fast forward to the 2015 release of ''Literature/{{Shimoneta}}''. Anna's character made the series a SleeperHit for the exact same reason. Moreso, since she's a more extreme version of Julia.
17** This wouldn't be the last time Creator/CharlieDay gets [[spoiler:[[Series/ItsAlwaysSunnyInPhiladelphia raped by a woman]]]].
18* JerkassWoobie: 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.
19* LoveToHate: Bobby Pellitt is a truly astonishing portrayal of the boss' spoiled son.
20* MagnificentBastard: [[ScaryBlackMan Dean "Motherfuckah" Jones]] is an ex-convict who started his life of crime stealing his drunk mother's money. Serving as Nick, Kurt and Dale's "murder consultant", he cons the three out of their money to give them mediocre advice on how to murder their corrupt bosses. Across the film, Jones [[DefrostingIceKing grows to enjoy the trio's company]], even helping Dale blackmail his boss to stop her sexual harassment. In the second film, he [[PetTheDog assists them in proving their innocence in Bert Hansen's murder]] and arresting the real culprit, Bert's son Rex. Soft-spoken and charismatic, [[KarmaHoudini Jones escapes the police]] to use the 5 million dollars Rex intended to use for his fake ransom plot to invest in Pinkberry.
21* MisaimedFandom: A large number of men claim they would love to be in Dale's position and have Creator/JenniferAniston rape them. Even in-universe, Nick and Kurt only have a limited amount of sympathy for Dale's situation and state that, compared to how things are with their own bosses, his "doesn't sound that bad."
22* MoralEventHorizon:
23** [[spoiler: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 AssholeVictim trope.]]
24** 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 dispose of the chemicals properly.
25** Julia crosses it when she [[spoiler:threatens to lie and tell his fiancee that he's a (false) sex offender]] and finally crosses it [[spoiler:in the sequel when she rapes Dale while he's in a coma]].
26** Rex crosses it in the sequel when he [[spoiler:kills his father]].
27** Bert crosses it when he [[spoiler:calls the police even after the trio threatens to kill Rex if he does, confirming that he loves money more than his own son]].
28* 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.
29* OneSceneWonder:
30** Creator/IoanGruffudd as a [[spoiler:male prostitute Dale mistakes for a hitman]].
31** Kenny Summerfeld. Most likely to succeed!
32** Creator/BobNewhart as [[spoiler:Nick's new boss at the end... who turns out to be a lunatic who punishes his employees by locking them in his car's truck.]]
33* SpiritualSuccessor: To ''Film/OfficeSpace''. Both movies feature three men getting revenge on their bosses (embezzlement in ''Office Space'', murder in this) and had Creator/JenniferAniston in the cast. Also half is kind of a spiritual sequel to the other Kevin Spacey evil boss movie ''Film/SwimmingWithSharks''; though it's not as dark and mean as Sharks, it does also feature an employee wanting to get revenge on their boss, though Guy actually almost goes through with killing his boss.
34* {{Squick}}:
35** In Horrible Bosses 2, Julia brags about shaving her lady parts with Dale's used razor.
36** In Horrible Bosses 2, when Nick says to Julia that he has to go to the bathroom, Julia seductively tells him to defecate on her.
37* TheWoobie: 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 DoubleStandardRapeFemaleOnMale responses from almost every other characters, and the he has to deal with his assailant blackmailing him with pictures she took ''of her sexually assaulting him'' to force to to comply. [[spoiler:And by the end of the sequel, he's been shot while trying to stop the bad guy, and Julia apparently raped him while he was hospitalized from this.]]

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