John Slattery in Mad Men
In the workplace, Roger Sterling (Slattery) has his eyes on big profits...and his sexy secretary.
Lana Parrilla in Once Upon a Time
Serving as the mortal enemy of Snow White and Prince Charming, Parrilla is nothing short of an Evil Queen.
Madeleine Stowe in Revenge
Victortia Grayson (Stowe) is the queen of the Hamptons and will do anything to protect her social status.
Steve Carrell & Ed Helms in The Office
The bosses at Dunder Mifflin can't help but crack not-so-hilarious jokes at their coworkers' expense.
Melinda Clarke in Nikita
Amanda (Clarke) is a master manipulator who has assumed control of Division.
Steve Buscemi in Boardwalk Empire
You should never trust Nucky, a corrupt Republican politician and gangster in Atlantic City.
Lauren Velez in Dexter
The Police Lieutenant is one tough, determined woman fighting for power in the political game among law enforcement.
Jack Gleeson in Game of Thrones
He may be the ruler of the Seven Kingdoms. But the character faces plenty of opposition from his own family who once called him a "vicious idiot."
Tim Matheson in Hart of Dixie
Dr. Brick Breeland (Matheson) is never hesitant to criticize Dr. Zoe's (Rachel Bilson) medical diagnoses and inexperience of Southern hospitality.
Meryl Streep in The Devil Wears Prada
If Anne Hathaway wants to move up from her assistant position, she will need to please her no-nonsense boss.
Colin Farrell in Horrible Bosses
What's it like working for a cocaine-addicted boss? Just look at how Bobby (Farrell) runs the place.
Jennifer Aniston in Horrible Bosses
Dr. Julia Harris (Aniston) sexually harasses her dental assistant. In fact, she threatens to tell his fiancée that he had sex with her unless he actually has sex with her.
Kevin Spacey in Horrible Bosses
Even though he tells his employee (Jason Bateman) a promotion could be in his future, he dashes all hopes when he awards it to himself.
Glenn Close in Damages
She may be brilliant. But lawyer Patty Hewes (Close) is also ruthless when it comes to winning a case.
David Harewood in Homeland
David Estes (Harewood) is the ambitious Director of the Counterterrorism Center of the CIA who was ultimately killed in a terrorist attack.
Montgomery Burns, The Simpsons
When you work for Mr. Burns, don't count on a promotion or pay raise.
Vanessa Williams in Ugly Betty
Wilhelmina may be pretty on the outside, but is anything but on the inside, especially to Betty (America Ferrera).
Jeremy Piven in Entourage
Nobody is safe when talent agent Ari Emanuel (Piven) gets bad news in the office.
Sally Field in Legally Blonde 2
When Elle Woods (Reese Witherspoon) champions for animal rights, she quickly learns her close friend could be her biggest enemy.
Gary Cole in Office Space
It can't be fun to have a boss who constantly whines about memos. Plus, he makes the staff work weekends.
Heather Locklear in Melrose Place
When your boss dates your roommate, things are bound to get a bit uncomfortable.
Michael Douglas in Wall Street
A young and impatient stockbroker is willing to do anything it takes to get to the top, something his "greed is good" boss is counting on.
Sigourney Weaver, Working Girl
She may look like a perfect lady. But Weaver has no problem stealing her employees' ideas and passing them along as her own.
Alec Baldwin in Glengarry Glen Ross
As a unethical real estate agent, Baldwin uses underhanded and dishonest tactics to make sales.