The 13 Worst Fictional Bosses


A bad boss can make even the greatest job seem like a 40-hour-a-week nightmare. But what makes a boss bad, exactly? Film and television offer us many examples: From the benign idiot to the manipulative greedhead to the boss from hell – literally – here are 13 fictional bosses we love to loathe.


13. Capt. James T. Kirk (William Shatner, Star Trek)

Captain James T. Kirk

As captain of the starship Enterprise, James T. Kirk commands a 430-member crew on a five-year mission to seek out new life and explore new civilizations, an assignment that places the entire ship in dire jeopardy at least once a week. Finding a way out of these jams almost always involves risky, death-defying gambits that save the day at the 11th hour. Sure, Kirk is an inspiring leader – unless you’re one of the red-shirted security officers who beam down to the planet with him, in which case Spock has calculated the statistical probability of your survival as zero-point-zero.

DEFINING MOMENT: To avoid crashing the Enterprise into a disintegrating planet, the only solution Kirk can come up with is a “controlled implosion” of the ship’s engines, something that has never been tried before and has a one-in-a-million chance of actually working.

MEMORABLE QUOTE: “Risk is our business. That’s what this starship is all about. That’s why we’re aboard her!”

FINAL VERDICT: As a boss, Kirk is not so much bad as he is dangerous to be around.


12. Jack Donaghy (Alec Baldwin, 30 Rock)

Jack Donaghy

Rising through the ranks to become NBC’s Vice President of East Coast Television and Microwave Oven Programming takes some serious political savvy, and Jack Donaghy recognizes corporate America is a Machiavellian minefield in which appearance is everything. Whether it’s deflecting blame, stealing credit or sucking up to the CEO, Jack plays the game with the best of them.

DEFINING MOMENT: Upon learning NBC’s new owner, Kabletown, derives most of its income from pay-per-view smut, Jack comes up with the idea of porn for females, in which handsome, well-dressed men listen intently as women talk about their feelings. 

MEMORABLE QUOTE: “Sometimes you have to change things that are perfectly good just to make them your own.”

FINAL VERDICT: Jack may be a pompous windbag with a worldview slightly to the right of Mussolini, but he’s also too busy climbing the corporate ladder to worry about what his employees are up to.



11. Charles Townsend (John Forsythe, Charlie’s Angels)

Charles Townsend

Like the Hooters of private investigation, Charlie’s detective agency is staffed exclusively with sexy young women, a clear violation of sexual-discrimination statutes. Straddling the fine line between proto-feminist and dirty old man, Charlie may empower the “Angels” in his employ, but he also exploits them, constantly placing them in harmful situations requiring minimal clothing. The ultimate hands-off boss, Charlie never even bothers to meet his employees face-to-face, preferring to delegate over the phone.

DEFINING MOMENT: A bra-less Jaclyn Smith running after a bad guy in slow-motion; you just know pervy old Charlie is hiding nearby with a pair of binoculars.

MEMORABLE QUOTE: “Good morning, Angels.”

FINAL VERDICT: Although his detective agency is a sexual harassment lawsuit waiting to happen, Charlie did give the Angels the responsibility they couldn’t attain in traditional law enforcement.


10. Larry Tate (David White, Bewitched)

Larry Tate

Back in the days when Mad Men would have been considered a documentary, TV viewers yucked it up at the avaricious antics of advertising executive Larry Tate, boss of Bewitched husband Darrin Stevens. Larry habitually oversteps boundaries, especially when he invites clients over to dinner at the Stevens household without warning, continually taking credit for Darrin’s work and, depending on the circumstance, his wife’s witchcraft. On the flip side, he has no qualms about foisting blame on Darrin if it means keeping his clients happy.

DEFINING MOMENT: Larry bullies Darrin into persuading warlock Doctor Bombay to market his magical cold-and-flu remedy.

MEMORABLE QUOTE: “Darrin, you old son of a gun, we’ve done it again!”

FINAL VERDICT: So what if he’s kind of a douche? Judging from Darrin’s lifestyle, working for Larry pays well enough to justify taking a little abuse now and then.


9. C. Montgomery Burns (Harry Shearer, The Simpsons)

C. Montgomery Burns

At the ripe old age of somewhere in the low three digits, the owner of the Springfield Nuclear Power Plant is the last of the robber barons, proud to have made his fortune the old-fashioned way – by stealing it. Although he can only treat his employees as poorly as the law will allow, “Burnsie” still pines for a bygone era when children could work in coal mines, the typical work day was 18 hours and any union could be busted with a few hired goons and a can of kerosene.

DEFINING MOMENT: Drilling for oil beneath an elementary school – and then being shot by a disgruntled toddler.

MEMORABLE QUOTE: “What good is money if it can’t inspire terror in your fellow man?”

FINAL VERDICT: Mr. Burns may be a power-hungry megalomaniac, but if an incompetent boob like Homer Simpson can hang onto his job for more than 20 years, how bad can he really be?


8. Bill Lumbergh (Gary Cole, Office Space)

Bill Lumbergh

A passive-aggressive middle-management weasel at a computer-software firm, Bill Lumbergh likes to pop in and out of his employee’s workstations without warning; that way, he can relay his often-unreasonable instructions without providing any opportunity to respond. Preferring to disguise his orders as suggestions, Lundbergh expects his wage-slave cubicle-drones to go above and beyond without offering any incentive.

DEFINING MOMENT: Bill reminds his staff that Friday will be Hawaiian Shirt Day: “So, you know, if you want to, wear a Hawaiian shirt and jeans.”

MEMORABLE QUOTE: “Uhhh, I’m also going to need you to go ahead and come in on Sunday, too. We’ve got some new people coming in and we need to play catch-up. Thanks!”

FINAL VERDICT: Creepy and insidious, Bill Lumbergh makes working in a cubicle that much more hellish.


7. Michael Scott (Steve Carell, The Office)

Michael Scott

Manager at the Scranton branch of failing paper company Dunder Mifflin, Michael Scott sums up his management philosophy as being “a friend first, a boss second, and probably an entertainer third.” Desperate to be liked by his indifferent employees, Michael devotes a fraction of his time to actual work, focusing primarily on time-wasting, awkward diversions that cause productivity and morale to plummet.

DEFINING MOMENT: After receiving a warning for making racially insensitive comments, Michael tries to atone by devising a diversity seminar that winds up being way more offensive than his previous comments.

MEMORABLE QUOTE: “Would I rather be feared or loved? Easy – both. I want people to be afraid of how much they love me.”

FINAL VERDICT: A benign idiot whose twisted affection for his employees inadvertently winds up harming them.


6. Ari Gold (Jeremy Piven, Entourage)

Ari Gold

Ari Gold may be one of Hollywood’s top agents, brokering multimillion-dollar deals for his movie-star clients, but to his terrified staff he’s a childish egomaniac with anger-management issues. Just ask his “gaysian” assistant, Lloyd, who is forced to suffer verbal harangues, humiliating treatment, crude sexual remarks and threats of violence on a daily basis.

DEFINING MOMENT: After regaining controlling interest in his agency, Ari strides through the offices with a paintball gun, blasting anyone he considers disloyal.

MEMORABLE QUOTE: “All right, I won’t fire her. I’ll just sexually harass her until she quits.”

FINAL VERDICT: While Ari is a walking train wreck, he’s not entirely unreasonable. He did eventually promote Lloyd, although it did take six seasons.



5. Miranda Priestly (Meryl Streep, The Devil Wears Prada)

MIranda Priestly

Rude, dismissive and downright nasty, Miranda Priestly is the legendary editor of the world’s most important fashion magazine, an imperious ice queen who expects her minions to bow to her every whim. Utilizing the management style favoured by most Third World dictators, Miranda’s impetuous demands keep her staff in a constant state of fear and uncertainty.

DEFINING MOMENT: Miranda tasks her new assistant with obtaining the unpublished manuscript of the next Harry Potter novel, the literary equivalent of breaking into Fort Knox, so her children will have something to read on the train.

MEMORABLE QUOTE: “Details of your incompetence do not interest me.”

FINAL VERDICT: She’s demonic, yes. But on the plus side, you’ve never been reduced to tears by someone so stylish!



4. Gordon Gekko (Michael Douglas, Wall Street)

Gordon Gekko

Gordon Gekko personifies the worst of 1980s Wall Street excess, a corporate raider who made zillions by buying controlling interest in troubled companies so he could fire the employees and sell off the assets. As rookie stockbroker Bud Fox (Charlie Sheen) learns, working for Gekko is not without its perks, although it’s only a matter of time before the SEC comes knocking at your door with a subpoena.

DEFINING MOMENT & MEMORABLE QUOTE: Gekko outlines his entire philosophy in this infamous speech: “Greed, for lack of a better word, is good. Greed is right. Greed works. Greed clarifies, cuts through, and captures the essence of the evolutionary spirit. Greed, in all of its forms; greed for life, for money, for love, knowledge, has marked the upward surge of mankind and greed, you mark my words, will not only save Teldar Paper, but that other malfunctioning corporation called the U.S.A.”

FINAL VERDICT: He’d sell his mother if it meant saving his own skin, so don’t expect him to visit you in prison when you’re serving three-to-five for insider trading.


3. Darth Vader (James Earl Jones, Star Wars)

Darth Vader

As the Emperor’s right-hand man, Darth Vader is entrusted with quashing the Rebel Alliance and overseeing construction of the Death Star. Something of a Luddite, Vader believes the Death Star’s new-fangled technology is nowhere near as powerful as his religious beliefs, which are, to put it mildly, extreme. Not only is Vader intolerant of other faiths, this single-mindedness carries through into the workplace, and he insists there is only one correct opinion – his. Anyone offering an opposing viewpoint usually winds up in a crumpled heap on the floor.

DEFINING MOMENT: When an Imperial officer dares to question Vader’s “sad devotion to that ancient religion,” Vader uses the power of the Force to choke him.

MEMORABLE QUOTE: “I find your lack of faith disturbing.”

FINAL VERDICT:  It’s easy to see why there were never any “casual Fridays” on the Death Star.


2. John Milton (Al Pacino, The Devil’s Advocate)

John Milton

If Lucifer were to actually take on human form and walk among us, it’s kind of a no-brainer that this fallen angel would become a lawyer. And not just any lawyer; John Milton is New York’s most sought-after attorney, with a reputation for getting his clients off scot-free, regardless of their guilt. Sly and seductive, Satan/Milton treats his employees exceptionally well, and doesn’t ask for much in return – only your immortal soul!

DEFINING MOMENT: Milton uses his power to compel some demons to possess a pair of homeless guys, who proceed to beat an opposing attorney to death.

MEMORABLE QUOTE: “Lawyers are the devil’s ministry.”

FINAL VERDICT: He’s the Devil – ’nuff said.





1. Tony Soprano (James Gandolfini, The Sopranos)

Tony Soprano

New Jersey mob boss Tony Soprano presides over a top-down, hierarchically structured organization that operates like a reverse pyramid scheme, with each underling kicking up a percentage of his earnings to his immediate superior, the cash trickling upward to Tony. Any good Mafia kingpin demands respect, which Tony achieves through a combination of violence, intimidation and the occasional homicide.

DEFINING MOMENT: Upon release from the hospital after being shot, a weakened Tony deliberately picks a fight with his muscle-bound bodyguard just so he can beat the bejesus out of the guy, thus sending the message that he’s still the alpha male in charge.

MEMORABLE QUOTE: “All due respect, you got no f*ckin’ idea what it’s like to be Number One. Every decision you make affects every facet of every other f*ckin’ thing. It’s too much to deal with almost. And in the end you’re completely alone with it all.”

FINAL VERDICT: Unlike more traditional industries, screwing up on the job doesn’t lead to a reprimand – it leads to getting whacked.



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