Hot Photo Gallery: Snakkle’s 10 Best Horrible Bosses

Richer and older than any man has a right to be, C. Montgomery Burns—better known as Mr.—owns the nuclear power plant that employs Homer and many other Springfield residents. His exxxcellent plots to make ever more money and keep his drones—er, workers—as oppressed as possible verge on the sinister, though Mr. Burns himself (voiced by Harry Shearer) is hardly an imposing figure. No one gets it as bad as his preternaturally loyal assistant, Waylon Smithers, who keeps coming back for more no matter how much disregard and outright abuse his beloved boss dishes out.

A genuinely bad boss, Michael Scott (Steve Carell) is also a mostly lovable one. While his staff try to go about their business, his philosophy is to make the workday as fun as possible, often to the detriment of actual, y'know, work. He's also perfectly comfortable with diverting any and all office resources to his own personal ends. Though he's known for race jokes, gay jokes, fat jokes, and age jokes, his favorites are sexual innuendos, especially "That's what she said." The only time he gets truly, intentionally nasty is with Dunder Mifflin's Scranton branch HR rep, Toby, whom Michael hates with a baffling amount of vitriol.

Famously based on Anna Wintour, the imperious editor-in-chief of Vogue, Miranda (Meryl Streep) keeps all her minions in line by terrifying them into going along with everything she says. As the arbiter of what's fashionable, she has the power to make or break people's careers—a fact that she both knows and relishes. Her own employees are treated like means to an end, and any misstep is instantly punished. She accomplishes all this with a demeanor so coolly nonchalant, you'd think she really couldn't care less as she tosses off a dismissive "That's all."

From his perch in the dispatch cage at the Sunshine Cab Company's garage, Louie (Danny DeVito) holds court over his drivers, insulting them at will, using wildly inappropriate language, taking advantage of anyone he can manage to bamboozle. When a new driver starts, he makes sure they understand the one word he never wants to hear them say: "accident." And you can be sure it isn't because he's concerned for their well-being.

When the sexually aggressive and bullying manager at the electronics store the title character works at discovers his little problem, she offers a simple solution: "I'm very discreet…but I'll haunt your dreams." It's got to be one of the weirdest and most awkward come-ons ever. Paula (Jane Lynch) also shares the story of her own first time in a truly creepy workplace overshare.

The only reality-star boss on our list earns his place with his OCD badgering, his arbitrary rules, and his (admittedly hilarious) abusive rants toward his employees. Despite his claim that he really cares about his staff, he consistently yells at them, throws mega-tantrums, threatens to let them go, and gives them genuine tear-inducing grief for transgressions like reading on the job or putting the wrong music on the CD player.

Two decades after the original movie came out, the hard-core go-for-broke philosophy glorified by Gordon Gekko (Michael Douglas) was eerily prophetic of the recent financial crisis. Gekko seems like the ultimate mentor for a young money- and status-obsessed broker, but he really only cares about his own wealth and status, preferably at the expense of everyone else. "Money never sleeps, pal—go to work" and "Greed is good" seem so ingrained in our cultural vocabulary now that you almost forget they came from a movie.

As a fast-paced, 24/7/365 Hollywood super-agent, he expects—no, requires—100 percent obedience from his employees. Though Ari (Jeremy Piven) can be downright cruel to his peons, firing people for literally being in the wrong place at the wrong time, he’s one of those rare bad bosses with a heart of gold. His constant barrage of bigoted nastiness to Lloyd would make him an inexcusably bad boss if it weren’t for the sweet, affectionate protectiveness that occasionally, against his better judgment, shines through. Entourage returns Sundays at 10:30pm starting July 24.

One of the most hilarious scene-stealers in a movie full of them, Les Grossman (Tom Cruise) is a stereotype of L.A. lunacy come to life. The high-strung, Diet Coke-swigging studio exec offers some, uh, pointed advice on how to handle actors before ordering the key grip via video chat to "hit that director in the face, really f***ing hard." He also demonstrates some dope dance moves in the memorable closing credits.

The ultimate cubicle-land middle manager, Lumbergh (Gary Cole) isn't evil or malicious, per se; he's just so happy to be a cog in the machine that it never occurs to him to treat his employees like people. Fixated on TPS reports and perfectly blasé while offhandedly mentioning "I'm gonna need you to go ahead and come in" on Saturday, this guy is like a vexing Dilbert­ cartoon come to life.