- Played By: Jason Bateman
An executive for a financial firm ran by David Harken. By the second film, he opens his own business along with his two best friends.
- Played By: Charlie Day
A dentist and assistant to Dr. Julia Harris whom she sexually harrasses. By the second film, he opens his own business along with his two best friends.
- Badass Beard: He finally lives up to the "badass" part when he blackmails Julia at the very end of the first movie.
- Jaywalking Will Ruin Your Life: Thanks to a drunken piss on an empty playground, Julia is the only dentist in town who will hire him.
- Played By: Jason Sudeikis
An accountant working for a chemical company ran by Bobby Pellit, the son of the late much benevolent boss. By the second film, he opens his own business along with his two best friends.
- Number Two: To Jack Pellett before his death.
- Played By: Kevin Spacey
Nick's boss. A cruel CEO that is constantly making horrible remarks to Hendricks.
- Ax-Crazy: When he goes after Bobby.
- Bad Boss: To Nick and eventually to Kurt and Dale, too.
- Big Bad: Out of the three bosses, he ends being the final villain when he kills Bobby Pellit in a fit of jealousy and the three protagonists witness him.
- Car Fu: During the car chase with Nick, Dale, and Kurt in the first movie.
- Clock King: He chastises Nick for being just two minutes late.
- Corrupt Corporate Executive: Shamelessly lies and manipulates to accrue money and power for himself.
- Crazy Jealous Guy: Harken constantly thinks that his wife is having an affair, it becomes evident when he finds Bobby's stolen mobile phone at his home and proceeds to kill him. When Dale is parked near his home and Harken has a diabetic attack, he gets furious that his wife thanks Dale for saving him. At the film's climax, Kurt shoves him that he had sex with his wife.
- Even Evil Has Standards: He may be a lying, murdering, power-tripping Jerkass, but ruining the livelihoods of employees is low, even for him.
- Evil Feels Good: Admits this to Nick and Dale when they confront him and trick him into confessing that he killed Bobby Pellit.
- Evil Has a Bad Sense of Humor: In the first movie, when Nick tells him he made him miss saying goodbye to his grandmother because he was working late for him, Harken apologizes... but then adds, "I had no idea your grandmother was named 'Gam-Gam'" as he dissolves into laughter.
- I Have a Family: He uses this on the police, although being a villain his use of this trope comes out pathetic.Harken: PLEASE PROTECT ME FROM THEM! I have a wife!..... and a cat!
- Jerkass: Doesn't even bother hiding his petty sadism.
- Jerkass Has a Point: In the second movie, he points out that, however horrible a boss he might have been, the "nice" guys running their company into the ground through their incompetence does a hell of a lot more damage to their employees than Harken ever did. Even Nick has to admit that it's a fair point.
- Murder the Hypotenuse: Or so he thinks, after finding Bobby's cell phone under a chair, thinking he's sleeping with his wife.
- The Sociopath: Treats his employees and his wife as tools and property rather than people, and is perfectly willing to commit murder.
- Stupid Evil: Just walks up to an innocent man at his door and shoots him likely thinking nobody was around to see or hear it and that no consequences would arise from it. On top of that, he kills the guy believing he's the one whom his wife is cheating on him with without even trying to verifying whether or not he actually was. And of course he wasn't.
- Ungrateful Bastard: To Dale, despite him saving his life.
Dr. Julia Harris, D.D.S.
- Played By: Jennifer Aniston
Dale's boss. A sexually harassing and lustful dentist.
- Bad Boss: To Dale, as she is constantly sexually harassing him, raped him while unconscious and menaces to seduce Dale's wife.
- A Date with Rosie Palms: In the first movie, while engaging in (forced) phone sex with Dale. During the climatic chase, no less.
- Depraved Dentist: She raped Dale while he was unconscious during a dental procedure aside from all the sexual harassment.
- Played By: Colin Farrell
Kurt's boss. The son of the late boss of a chemical company, he is a drug addicted, party-hard and sexually active manchild who doesn't really cares about the company and its employees.
- Asshole Victim: He gets shot by Harken halfway through the first movie.
- Bad Boss: Becomes Kurt's early on in the first movie after Jack's death.
- The Hedonist: After becoming boss of Pellit Chemicals, he spends his days partying with women in his office.
- Inadequate Inheritor: Bobby's father Jack was an upstanding Benevolent Boss who genuinely cared about his employees and ran his company responsibly. Bobby is a selfish cokehead who makes no secret of his plans to cut corners in his operations and layoff employees to squeeze every ounce of profit out of the company before gutting it completely and retiring.
- Tyrant Takes the Helm: Almost immediately after becoming the boss, Bobby plans to lay people off and cut corners in their waste disposal operations, and he makes no secret that he hates the company and wants to gut it entirely.
- "Well Done, Son!" Guy: It's implied that he resents Kurt in particular because of the close relationship Kurt had with his father.
Dean "Motherfucker" Jones
- Played By: Jamie Foxx
A criminal who "trains" the protagonists.
- Awesome Mc Coolname: He named himself "Motherfucker Jones" as his real name is the same as another actor. Thing is that he got it after fucking up his mother... by stealing her wallet from her purse.
- Greed: His main personality trait. His nickname comes from his attempt to empty his mother's pockets.
- Jerk with a Heart of Gold: He may a low-life seeking to get as much cash as he can, but he does seem to be on friendly terms with the trio as he does offer them advice as promised when he payed them and even went out of his way thing to help them deal with some issues they had like recording Julia to help Dale blackmail her into stop sexually harassing him and tried to help them expose Rex.
- Karma Houdini: He gets away with $5,000 in the first movie from merely Nick, Dale and Kurt's own pockets and in the sequel he steals $5,000,000 in cash which he uses to invest in Pinkberry.
- The Obi-Wannabe: He overcharges the trio for criminal advice which isn't even any good. He knows his advice is not superb, he just wants to cheat them out of their money.
- Scary Black Man: Played for Laughs. He has a very tough appearance, always talking seriously and he sometimes intimidates the trio.
- Played By: Donald Sutherland
The late boss of Kurt and the chemical company he ran, he was also the father to Bobby Pellit.
- A Father to His Men: He had Kurt in high consideration, like a son, something that Bobby never liked.
- Benevolent Boss: Jack cared about his employees and tried to ran his company with enviromental awareness.
- Played By: P.J. Byrne
A broke guy who befriends Nick, Dale and Kurt but also begs them for money. Whenever the three men are depressed, they remind themselves at least they're not Kenny.
- Basement-Dweller: It is implied he and his wife are living at his mother's.
- How the Mighty Have Fallen: He went straight to working for Lehman Brothers after graduating from Yale making the high six figures but due to the company's bankruptcy, he's gone broke. But then to be completely broke after making that kind of income is his fault as well because he should've saved up for the future.
- Lower-Class Lout: Kenny is a painful reminder to Nick, Dale and Kurt that quitting their jobs just to escape their abusive authorities is not an option because they'd have no income and wind up like Kenny.
Gregory (real name Atmanand)
- Played By: Brian George
- The Voice: He's in a call center in India. We only hear him talk through the car's speakers.
- Played By: Julie Bowen
The blond and naïve bombshell wife of David Harken.
- Dumb Blonde: She fails miserably to conceal any evidence she cheats on her husband.
- Your Cheating Heart: She kisses Dale on the cheek and performed oral sex on Kurt in her own bathroom during her husband's surprise birthday party. She seems to be very bad at covering up her acts of cheating on her husband, as David has accused her of fucking every man in their neighborhood.
- Played By: Chris Pine
The son of Bert Hanson. He plans to help the main trio with their business with a forced ransom and dethrown his father.
- Big Bad: Of the second movie. He wants to take his father's business (because his father is worth billions of dollars) and kills him framing Kurt, Nick and Dale for the assassination.
- Evil Laugh: When he kills his father for refusing to deliver the blackmail money.
- Hidden Depths: Rex is capable of coming up with convoluted plans very quickly.
- It's All About Me: Resorts to KILLING (his weapon is a Colt Python) for the pursuit of money.
- Jerkass: Due to being the Big Bad of course.
- Psychopathic Manchild: Acts like a child, always begging for money from his dad and crying when he doesn't get it.
- Spoiled Brat: He cried over his dad refusing to pay the $5 million blackmail bond.
- Played By: Christoph Waltz
An investor that helps at first with the main trio's rising business in the second film.
- Asshole Victim: No one will miss him.
- Corrupt Corporate Executive: While already a billionaire, he swindled Nick, Dale and Kurt out of their money and business just to get even slightly richer.
- Disc-One Final Boss: He is set up to be the Big Bad, but gets killed off by Rex.
- Jerkass: He's greedy and a con artist.