Avery Tolar (The Firm)
The Movie Boss: Avery Tolar (Gene Hackman) is the head of The Firm in Memphis, and mentor to young law graduate Mitch McDeere (Tom Cruise).
Gifted a house and a car, Mitch is blinded by Tolar’s generosity until two associates turn up dead…
Cruellest Moment: Killing anybody who attempts to leave The Firm.
Robert Pujol (Potiche)
The Movie Boss: A tyrannical businessman, Robert Pujol (Fabrice Luchini) owns his own umbrella factory, which he governs with a cruel imperiousness.
Cruellest Moment: Robert’s evil ways provoke his workers to go on strike.
Bernie Lomax (Weekend At Bernies)
The Movie Boss: Dead for pretty much the entirety of Weekend At Bernie’s , Bernie Lomax (Terry Kiser) is nevertheless a horrible boss while alive.
As the chief of a New York insurance company, he fiddles the books and doesn’t take kindly to those who question him.
Cruellest Moment: When he learns that two of his employees have found out about his life insurance fraud, he sends the mob after them…
Velma Von Tussle (Hairspray)
The Movie Boss: The racist manager of a TV station, Velma Von Tussle (Michelle Pfeiffer) is a former beauty queen who spends much of her time putting teenage girls down for the way they look.
She’s also not above cheating (she slept with judges to win beauty contests).
Cruellest Moment: Velma encounters Tracy’s mother (John Travolta) and isn’t afraid to let rip with a few barbed insults.
“Mrs. Turnblad! I'd know whose mother you were ANYWHERE,” she drools. “Oh, let me guess - new dress? You'll stop traffic!”
Robert Hanssen (Breach)
The Movie Boss: A senior FBI agent, Robert Hanssen (Chris Cooper) is suspected to be a sexual deviant and has a very odd outlook on power in the FBI.
For one, he believes that only those who regularly shoot their guns are considered for senior positions at the organisation.
Cruellest Moment: Though he’s generally kind to his undercover assistant Eric O'Neill (Ryan Phillippe), Hanssen keeps secrets – the biggie being that he’s spying for Russia. Bad boy.
Colonel Nathan R. Jessup (A Few Good Men)
The Movie Boss: The no-nonsense Colonel (Jack Nicholson), who commands the Guantanamo Bay Naval Base in Cuba with a firm hand and a toothy leer.
Cruellest Moment: “You can’t handle the truth!” The full extent of Jessup’s cruelty is revealed when he’s questioned on the stand about the death of PFC William Santiago (Michael DeLorenzo).
It turns out he all but covered the entire thing up.
E. Edward Grey (Secretary)
The Movie Boss: Though Lee Holloway (Maggie Gyllenhaal) is unprofessional and not exactly dressed for the job, attorney E. Edward Grey (James Spader) hires her as his secretary.
Then reveals he has some rather unorthodox methods for dealing with her shortcomings…
Cruellest Moment: Disgusted with his own predisposition for BDSM, Grey fires Lee after a particularly steamy encounter in the office.
It’s particularly cruel considering she’s in love with him…
David Harken (Horrible Bosses)
The Movie Boss: The President of Comnidyne Industries, David Harken (Kevin Spacey) is a malicious manipulator who delights in sadistically messing with his staff’s minds.
Director Seth Gordon admitted that the character was based on several real life bosses. We’d love to know who they were…
Cruellest Moment: Right at the beginning of the film, Harken hints that Nick (Jason Bateman) is about to get promoted – and then announces to the company that he’s taken the job himself.
Captain Vidal (Pan's Labyrinth)
The Movie Boss: Stepfather to young Ofelia and a Falange officer, Captain Vidal’s (Sergi López) cruelty knows no bounds.
“He is the most evil character I've ever played in my career,” acknowledges López.
Cruellest Moment: Vidal is violent to the extreme, setting a bloody example for his men by brutally butchering anybody he considers to be a rebel.
Take the moment when he kills two men who could be rebel allies, or could just be farmers…
Capt. Queeg (The Caine Mutiny)
The Movie Boss: Captain of the Navy during World War II. He’s so crackers that he decides to spend more time accusing his crew of stealing strawberries than actually, y’know, saving the world.
Cruellest Moment: While under enemy fire, Queeg abandons a group of landing craft, leaving them to fight on their own.