Is your boss a slave driving psycho?
Nick has sacrificed everything for his job, and claims that the difference between him and life's failures is that he's willing to take it. He spends six months sucking up to Harken to get promoted--and then he finds out that the position he's trying for will be eliminated.
Their mutual friend Kurt used to like his job, and his boss, Pellitt. Pellitt just had a heart attack, and his son Bobby is in the process of running the company into the ground.
One night, Kurt suggests that they kill each other's bosses. He means it as a joke. At first.
- Abhorrent Admirer: Julia, at least to Dale. She probably wouldn't be this to many other guys (assuming they're single).
- A Date with Rosie Palms: Julia while she's on the phone with Dale.
- Actor Allusion: Someone mentions Strangers on a Train, and Dale "recalls" that Danny Devito was in it. To drive the joke home, the argument that ensues strongly resembles the sort of pointless banter that would appear on It's Always Sunny in Philadelphia.
- A Man Is Always Eager: Averted with Dale and played straight with Kurt. Dale rejects Julia's advances because he's engaged and because it's unethical to sleep with one's employer, whereas Kurt is a horndog who hits on every pretty woman he meets.
- A Million Is a Statistic: Bobby Pellitt's willing to let thousands of people in Bolivia die rather than pay extra to properly dispose of chemicals.
- Anything That Moves: Julia and Kurt.
- Asshole Victim: Pellitt.
- Awesome McCoolname: "Motherfucker" Jones. He got his name when his mother was passed out drunk and naked, and he stole the money out of her purse. Yeah, he really fucked her over.
- Ax Crazy: Harken, who is a power-tripping Jerkass to begin with, easily makes the transition to psychotic murderer.
- Badass: "Motherfucker" Jones, subverted. He just appears and sounds Badass. He never committed a murder, simply giving advice to the main characters off his own speculation. In reality, the only reason he went to jail was for video piracy. He's not even that great a negotiator.
- Bad Boss: Yup. It's right there in the title.
- Bad Guys Do the Dirty Work: The only murder in the movie is when Harken kills Pellitt.
- Bald of Evil: Bobby, however hard he tries to cover it with that awful combover.
- Beard of Evil: Bobby.
- Benevolent Boss / Cool Old Guy: Bobby's father is this before he dies and his son takes the helm.
- Beware the Nice Ones: Every once in a while, Dale snaps.
- Big Bad Ensemble: The three horrible bosses. By the final act of the movie, however, Harken emerges as the true Big Bad.
- Bi the Way: Apparently, Bobby.
as hookers are leaving his house
- Black Bra and Panties: Julia undresses in front of a window and then parades around the house in nothing but (plus suspenders and stockings) as Kurt watches.
- Black Comedy: Though it's ultimately surprisingly idealistic--only one character is capable of murder and it's one of the titular bosses.
- Bowdlerise: At least some versions of the poster featuring the faces of the three bosses, Julia is described as a "Nympho" rather than the somewhat softer "Maneater" that can be seen at the top of the page.
- Briefcase Full of Money: Jones's fee, although it doesn't completely fill the briefcase he demands.
- Brick Joke: Kenny, the mutual friend of the three protagonists who will do anything for money.
- Butt Monkey: The three protagonists.
- The Cameo: Bob Newhart as Nick's new boss, a "Twisted Old Fuck".
- The Cop who pulls Nick over for speeding is THE OLD SPICE GUY!!!
- Cat Scare: Happens three times, though only the first time is it scary.
- The Charmer: Kurt seems to be quite a ladies' man.
- Chekhov's Gunman: There are three, actually. "Motherfucker" Jones and Kenny both end up helping Dale blackmail Julia, while Kurt's onboard navigator Gregory helps prove that Harken was the one who killed Bobby.
- Comic Trio: Kurt, Nick and Dale, complete with frequently slapping each other.
- Completely Missing the Point: In-universe, Nick and Kurt fail to see how Dale being repeatedly sexually assaulted by his psychopathic boss is all that bad, just because... well, 'cause she's Jennifer Aniston. A lot of audience members feel the same way.
- In fairness, they do see it as a problem, it's just that they don't think it's in the same league as their issues:
Nick: I'm such a sucker! Harken was never gonna promote me...
- Cool Old Guy: Jack Pellitt.
- Corrupt Corporate Executive: Bobby who has no problem dumping harmful chemicals to save Money.
- Crazy Jealous Guy: Harkin
- Dead Star Walking: Donald Sutherland as Jack Pellitt. Quite obvious given the film's basic premise.
- Depraved Dentist: Julia, on a scale not seen since Steve Martin wore a gas mask in Little Shop of Horrors.
- Digital Piracy Is Evil: Why Motherfucker Jones spent ten years in prison.
- Distracted by the Sexy: Kurt gets this. Badly. Twice. Once with his intended murder victim and later during an Engineered Public Confession.
- Double Standard Rape (Female on Male): The film's position on this is a little murky. On the one hand, Dale is upset by what happens and calls Julia a rapist and she is clearly portrayed as a horrible person, but the sexual harassment scenes are also Played for Laughs. On the other hand, Dale's friends, and a good portion of the audience, clearly believe that Rape Is AWESOME When It's Jennifer Aniston.
- Note that Dale's the only one of the three in a relationship, and his fiancee is barely in the movie. She basically only exists to give credence to the idea that him being sexually harassed is an actual problem.
- Drugs Are Bad: Bobby has seriously messed himself up on cocaine.
- Dude, She's Like, in a Coma: Julia's job allows her to drug men unconscious. She takes advantage of this at least twice.
- Hoist By Her Own Petard: Dale takes advantage of this at the end to trick her into nearly raping his (very much awake) friend.
- Dumb Blonde: Harken's wife Rhonda doesn't seem the brightest bulb, being unable to tell what guests she invited to a party she is organising.
- Engineered Public Confession: Double Subverted.
- Erotic Eating: Julia eats a popsicle, a banana, and a hot dog, in that order. Kurt is dumbfounded.
- Well, it is cold to hot.
- Even Evil Has Standards: Apparently, Julia does respect the sanctity of marriage. Although, this only means Dale has until the wedding to have sex with her, willfully or not.
- Evil Feels Good: Not who you'd think; it's actually Harken who starts to like killing.
- Evil Has a Bad Sense of Humor: Nick tells Harken that it was due to his long hours that he was unable to say goodbye to his grandmother, whom he calls "Gam-Gam," while she was dying. Harken responds by laughing at the fact that Nick called his grandmother "Gam-Gam."
- Expy: Harken is basically Buddy Ackerman, played for laughs. Also, Wendell Pierce's cop character is basically Bunk Moreland from The Wire partnered with Ron White. Dale has more than a few similarities with Charlie, right down to his Artistic License: Law derived from watching Law and Order.
- Extreme Doormat: Nick. Dale and Kurt stand up to their respective bosses from the get-go--albeit to no avail--but Nick doesn't assert himself with Harkin until after Harkin reveals that he's not going to promote him; Nick even says in voiceover at the beginning of the film "that the key to success, and no one will teach you this in business school, is taking shit."
- Four-Temperament Ensemble: The three bosses are choleric (especially Harkin), Nick is phlegmatic, Dale is melancholic, Kurt is sanguine.
- Here We Go Again: Nick's new boss.
- Hookers and Blow: Bobby's principal interests.
- IKEA Erotica: Julia calls Dale and demands that he describe how he'd pleasure her. He improvises. Poorly.
- Indulgent Fantasy Segue: When Nick throws Harken out of a window, to the cheers of his coworkers.
- Intimate Psychotherapy: Kurt tries this on Julia. It doesn't work very well.
Dale: Good job fucking the crazy out of her, man.
- Is This Thing Still On?
- It's All About Me: Bobby's attitude is basically this.
- Jerkass: All three of the titular bosses.
- Karma Houdini: Only Julia ends the movie with job and life intact. To be fair, she did get blackmailed in a Crowning Moment of Awesome for Dale, and due to his sex offender registration, who else would hire him besides her?
- To be fair, while her treatment of Dale was inexcusable, she wasn't a Complete Monster like Harken and Pellett.
- Kavorka Man: Kurt.
- Lack of Empathy/No Sympathy: The titular bosses.
- Large Ham: Dale.
- Make It Look Like an Accident: The trio plan to take advantage of the fact that Pellitt is a cocaine addict and that Harken is allergic to peanuts to poison them. They don't actually do either of these things, as Harken kills Pellitt and goes to jail for it.
- Major Misdemeanor: Dale got drunk at a bar that was next to a playground, and committed public urination. It was night, and there were no kids there, but he's still a registered sex offender, which is why he's stuck working for Julia.
- And Motherucker Jones spent 10 years in prison for pirating Snow Falling on Cedars.
- Manipulative Bastard: Harken.
- The Millstone: Dale is more or less to this film what Alan is to The Hangover.
- Kurt's out-of-control libido and fondness for vulgar jokes doesn't help, either.
- Mistaken for Pregnant: "Large Marge"
- Murder the Hypotenuse: Why Harken kills Pellitt -- the irony being that the victim isn't actually the hypotenuse.
- My Name Is Not Durwood: The guys make a genuine attempt to call the GPS guy by his real name (Atmanand) but give up and switch back to Gregory.
- Name's the Same: Motherfucker Jones' full name is Dean Jones. He points out that he couldn't be in the bar "with that Disney-ass name".
- Nice Guy: Dale is what happens when you take the standard sweet, innocent working girl who gets sexually harassed in movies like Nine to Five, flip her gender, and change absolutely nothing else. He's not exactly effeminate, and he's definitely not camp, but he's still a very unusual example of a positively portrayed straight male character with traditionally feminine virtues and flaws. (Then again, he also has the buried rage common in said working girls . . .)
- Nice to the Waiter: If only the bosses had treated their employees with something resembling decency, they wouldn't have ended up dead ( Bobby Pellitt), blackmailed ( Julia) and most likely being gang raped in prison ( Harken)
- Jack, Kurt's original boss, by contrast is shown as being extremely good to employees and a very honest businessman. This only makes how Bobby turned out more of a mystery.
- Only Sane Man: Nick.
- One-Scene Wonder: Ioan Grufford as a male prostitute Dale mistakes for a hitman.
- Colin Farrell has only two speaking scenes as Pellitt, but he utterly owns both of them.
- Parental Incest: Subverted with "Motherfucker" Jones. When he's explaining how he got his nickname by sneaking into his mom's bedroom one night. As it turns out, he simply stole her money, fucking her OVER.
- Playing Against Type: Two of the three titular bosses.
- Plot Allergy: Harken is lethally allergic to peanuts.
- Politically-Incorrect Villain: Pellitt.
- The Pornomancer: Kurt.
- Prison Rape: What Harken has to look forward to for twenty-five years, according to Nick.
- Psychopathic Manchild: Bobby, again.
- Reasonable Authority Figure: Bobby's dad is the ONLY one in the entire movie.
- Sesquipedalian Smith: Motherfucker Jones.
- Sexual Extortion: Julia does this to Dale as part of a concerted campaign of sexual harassment.
- Sir Not-Appearing-In-This-Trailer: Donald Sutherland.
- Small Name, Big Ego: Pellett. Good god, Pellett. His apartment is aptly described as "Looking like the inside of the mind of an asshole".
- Smug Snake: Harken and Pellett.
- The Sociopath: Arguably, Harken.
- Spiritual Successor: To Office Space. Both movies feature three men getting revenge on their bosses (embezzlement in Office Space, murder in this) and had Jennifer Aniston in the cast. Also half is kind of a spirtual sequel to the other Kevin Spacey evil boss movie Swimming with Sharks, though its not as dark and mean as Sharks it does also feature a employee wanting to get revenge on their boss though Guy actually almost goes through with killing his boss.
- Strangers on a Train Plot Murder: Name-checked.
- Take This Job and Shove It: Nick tries this. Then he finds out that to get another job, he'd need Harken's recommendation, and Harken wants him right where he is. This culminates in Harken calling him his "bitch."
- Dale also threatens this, but no one else would hire him -- see Major Misdemeanor.
- Taught by Television: Dale learned enough practical law from Law and Order to know that the cops can't hold him if they can't charge him with anything.
- Throw It In: 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.
- Too Dumb to Live: Nick and Dale confronting Harken, who they know to be a sociopathic murderer, completely unarmed.
- The general incompentence of the trio is a large part of the humor. As the movie goes on it becomes obvious they couldn't kill an ant without getting themselves injured or screwed over in some way, let alone commit a triple homicide.
- Trailers Always Spoil: A few trailers reveal important plot twists, such as Dale saving the life of Nick's boss. One red band trailer shows that Kurt sleeps with Julia while stalking her to plot her murder.
- Trouble Entendre: the entire conversation with 'the Wetwork Man'.
- Tyrant Takes the Helm: Bobby Pellitt, a hedonistic Jerkass who takes over his late father's company and uses it as his personal piggy bank.
- Wet Sari Scene: Julia inflicts this on Dale, although she seems to have a better view than the audience.
- Unusual Euphemism: "Wet work" does not mean a hitman. It means a man who'll urinate on you for cash.
- "I'd like to bend her over a barrel and show her the fifty states." Kurt is referring to screwing Harken's wife.
Nick: What's that mean?
- What Could Have Been: Ashton Kutcher auditioned for the role of Dale, while Jeff Bridges, Tom Cruise, and Philip Seymour Hoffman were all considered for the part of Harken.