Played by: Steve Carell
Where He Works: Dunder Mifflin Paper Company in Scranton, Pa. He is a manager.
Management Style: Scott is the kind of boss who desperately wants to be your friend. And so he often forces his workers to attend events with him outside of work. For instance, Scott requires attendance at his annual awards show for his workers called, "The Dundies." As the self-appointed host of the program, Scott takes turns singing covers of songs like "You Sexy Thing" while his workers stare on helplessly.
He's also famously incompetent and shockingly insensitive. At one point, Michael injures his foot after he steps on a George Foreman grill and he's disappointed when his workers don't seem to treat him with enough sympathy when he shows up on crutches. So he invites a colleague who is physically disabled to discuss what life in a wheelchair is like.
Quote: "Sometimes I'll start a sentence, and I don't even know where it's going. I just hope I find it along the way. Like an improv conversation. An improversation."
Voiced by: Harry Shearer
Where He Works: Springfield Nuclear Plant. He is the owner.
Management Style: Burns is the cartoon version of the outrageously-rich, unscrupulous corporate titan who only cares about the bottom line. He can't be bothered to remember the names of even some of his longtime employees, including Homer Simpson. Whenever Burns comes across a problem or is asked to donate to charity, his response is to "release the hounds" -- and immediately his attack dogs arrive to deal with the problem.
He will do anything to increase profits. A high point on the series: Burns creates a shield to block out the sun so the residents of Springfield are forced to use more electricity powered by his nuclear plant. And finally, Burns should have walked away from the job long ago. His advanced age is an ongoing joke on the show and is demonstrated by his constant use of archaic words -- "score" for "20;" "petroleum distillate" for "gasoline;" and "jumping box" for "television."
Quote: "I think I'll donate a million dollars to the local orphanage. When pigs fly!"
Played by: Jon Hamm
Where He Works: Manhattan advertising firm Sterling Cooper; later the new firm, Sterling Cooper Draper Pryce, which has since merged with Cutler Gleason & Chaough. He started as a creative director.
Management Style: Draper is the brilliant and dashing but flawed boss. He has risen in the New York advertising industry of the 1960s because of his visionary work and ability to charm men and women alike. He's also a brilliant tactician. Early in the show, he comes up with an ad campaign for Lucky Strike cigarettes that will help the brand survive the new attention cigarettes then began receiving over causing cancer. He comes up with a slogan: “It's Toasted.”
Draper, like many successful leaders, is less successful in personal relationships. His first marriage falls apart due to his constant womanizing. His second marriage isn't too stable, either, thanks to his personal demons. He can be imperious with underlings, but people find him irresistible and charismatic.
Quote: "What you call love was invented by guys like me, to sell nylons."
Played by: Ian Abercrombie
Where He Works: Doubleday Publishing. He is an executive.
Management Style: Mr. Pitt is the quirky boss who makes strange demands. He asks Elaine, who works as his assistant, to complete soul-crushing tasks. She must pick out the "perfect" pair of socks for him to wear. And of course, he doesn't like any of them because they don't stay up, they're too tight or they're not comfortable enough. She's also assigned the task of removing salt from his pretzel sticks.
Indeed, working life with Mr. Pitt requires a constant tolerance for ridiculous behavior. Mr. Pitt is excessively formal -- he eats his snickers with a fork and knife. He also has bizarre interests. He spends time focusing on winning a contest so he can help hold up the Woody Woodpecker balloon in the Macy's Thanksgiving day parade. He's also easily distracted; he spends days staring into a 3-D painting when he should be focused on a business meeting to discuss a new merger.
Quote: "I want a decent sock that's comfortable that will stay on my foot!"
Played by: Gary Cole
Where He Works: Initech software company. He is a vice president.
Management Style: Lumbergh is the corporate bully who thinks he's a smooth operator but is just painfully obvious. He greets his workers with the same smarmy catchphrase -- "What's haaappening?" He constantly uses the same sayings -- "I'm gonna need you to" and "if you could just go ahead and" -- to assign tasks as if they were pleasant or optional when they are anything but. And of course, Lumbergh' is almost always checking up on the progress of "TPS reports," the mind-numbing paper-pushing his workers are forced to complete.
He's also shameless about his big paycheck. Each day, he drives to work in a Porsche that has a vanity license plate that reads "MY PRSCHE." He's so over the top he even makes the bizarre fashion choice of wearing both a belt and suspenders at the same time.
Quote: [Voice Message] "Hello Peter, what's happening? mmm, I'm gonna need you to go ahead come in tomorrow. So if you could be here around 9 that would be great, mmmk... oh oh! and I almost forgot ahh, I'm also gonna need you to go ahead and come in on Sunday too, kay. We ahh lost some people this week and ah, we sorta need to play catch up."