As we bid Michael Scott a fond farewell as he walks away from Dunder Mifflin, we realized that there are few bosses who have made much of an impact in the world of entertainment. Most of them are just a device to motivate the main character, but there are a few who stand out, for reasons both good (they have your back) and bad (they might kill you). Others still are just odd, or can be both a spectacular boss and the most irritating prick on the planet. Here is a list of our favorite bosses of all stripes. As always, feel free to leave your polite, well considered opinions in the comment section.
The Good
Jimmy James (Stephen Root, “NewsRadio”)
He likes to think of himself as a capitalist lion tamer, but books don’t lie: dude is a macho business donkey wrestler, and don’t you forget it. James plays the kinds of big business games that we proles often fantasize about, where billionaires play poker and use their corporations as chips (he lost WNYX in a game, but faithful reporter and math wiz Lisa Miller won it back). He also treats his efforts to find a wife with the same no-nonsense business acumen that he would use to broker any deal. (He came close to making the deal once, but the location of the vacation house turned out to be a deal breaker.) The bottom line is that while Jimmy James micromanages the talent at his radio station, he is not a hatchet man by nature, and pretty much lets the lunatics run the asylum. Works for us.
Captain Jack Harkness (John Barrowman, “Torchwood”)
He can’t be killed. Think about that – whatever happens at work, your boss will not die. Isn’t that the kind of person you want to be close to? Granted, most of the people who work with Captain Jack Harkness end up dead, and once you agree to work for Torchwood, the Cardiff-based secret organization that prevents alien attacks, you are not allowed to quit. Plus, Jack is not afraid to make the tough decision, even if it means sacrificing his grandson in order to save the children of Earth. But no high-reward job comes without its share of risk, and if you’re going to risk your life fighting aliens on a daily basis, you want Jack Harkness in your corner.
Jack Donaghy (Alec Baldwin, “30 Rock”)
Jack Donaghy is, for lack of a need for any other definition, a man. He is the man we all aspire to be, even the hipster kids among us. He is tireless, unflappable, and totally at the top of his game. Before meeting his wife, he was chasing tail with Bob Ballard and drinking wine from ancient Phoenician amphoras. He consumes scotch like water. Jack Donaghy named his fists Saint Patrick and Saint Michael, a fact we know only because those fists were used to fight his own father. He eschews the familiar and espouses the opulent. Most of all, he somehow finds it in his arrogant heart to mentor one of the strangest bosses around: Liz Lemon.
Angel (David Boreanaz, “Angel”)
If there is anyone on this list that we want by our side in an alley fight, it’s Angel, a.k.a. Angelus, the most vicious vampire who ever un-lived. Cursed with a soul after murdering a young gypsy girl, Angel has learned to quench his thirst for blood in more humanitarian ways, while spending the rest of his undead days trying to destroy the Senior Partners of Wolfram & Hart, which is basically Satan’s law firm. Like Harkness, working for Angel is by no means a safe career path – as Cordelia Chase and Winnifred “Fred” Burkle could attest, if they weren’t dead – but Angel stands up for the weak, takes on the big guy, and will stop at nothing to make sure that justice is served. Nice to know there are still a few bosses out there that have your back.
The Bad
The list of candidates for this category is an admittedly long one, so for the sake of simplicity, we’re paring our list down to four most foul supervisors.
Charles Montgomery Burns (Harry Shearer, “The Simpsons”)
His nuclear plant needs hundreds of millions in repairs in order to bring it up to code. (And that was in the early, ’90s, so adjusted for inflation, it could be billions now.) He gave his employees stock, but only after they waived certain constitutional rights. He once embarked on a massive recycling program, but only to fuel a company that uses the six pack rings to strip the oceans of all sea life. He sold weapons to Hitler. Lastly, he tried to block out the sun so people would use more power from his plant. No one has ever really had a boss who wringed his hands, or had an entire walk-in closet of clothes made from exotic animals, but Montgomery Burns represents everything we loathe about bosses in the real world, whether it’s a lack of compassion for non-work commitments or the tendency to throw employees under the bus for personal gain. He might be a caricature of evil, but he’s still evil.
Bill Lumbergh (Gary Cole, “Office Space”)
Lumbergh, meanwhile, is terrifying because he is one of the most realistic bosses the entertainment world has ever seen. Promoted beyond his skill set — assuming he even has a skill set — Lumbergh knows he has a good thing, and he’ll be damned if he’s going to lose his cushy job to any of the peons beneath him, so he micromanages the bejeezus out of them, makes them work on weekends, and will even steal their cubicle walls if it helps drop employee morale. Monty Burns is playing at the Oprah level of power; there are only a handful of people with that kind of influence. But Lumbergh…the corporate world is littered with guys like him. God help us.
David Brent (Ricky Gervais, “The Office”)
We had to include the man who started it all. Look at that picture. That is why David Brent is a terrible person to work for – he’s a man-child, desperate for attention and woefully lacking self-awareness. He makes jokes about firing people, and will use training sessions as an opportunity to play songs on the guitar for his captive employees. He takes a position with corporate that leads to his employees getting sacked, and wonders why they’re not happy for him. His jokes are in poor taste, he’s a lousy motivator, and in his desire to be everyone’s friend, he is oblivious to their problems and doesn’t help anyone in a meaningful way. David Brent is the kind of guy that no one chooses to work for – he’s thrust upon people. Sad, sad, unlucky people.
Patty Hewes (Glenn Close, “Damages”)
Working for Patty Hewes is much like working for the Dread Pirate Roberts: even when you do good work, she’ll most likely kill you in the morning. None of her actions can be taken at face value; more than likely, she’s four or five steps ahead of everyone else, and is not afraid to step color outside the lines (while making sure her tracks are well covered) if it means winning a case. When a potential witness was reluctant to testify against her former employer, Patty had her dog killed, and made it look like the defendant was responsible. When a doctor prescribed bed rest for a young and very pregnant Patty, she walked herself into a miscarriage so she could take her first job. To call her heartless is an insult to the heartless – Patty Hewes is a functional sociopath, and working for her will haunt you for the rest of your life.
The Strange
Michael Scott (Steve Carell, “The Office”)
Like some of his fellow head honchos on this list, Michael Scott is a tough boss to categorize. On the one hand, he genuinely cares about his employees (well, everyone except Toby…and probably Dwight), but his atrocious people skills and, um, unorthodox management style often make him a colossal headache in the Dunder Mifflin offices. Forget about getting any work done if he’s hovering around your desk, particularly when he calls for an impromptu meeting in the conference room, and his repeated appearances at sensitivity training seminars clearly haven’t paid off, to which Oscar can attest. But Michael is kind, loyal and honest (generally speaking, of course), and while productivity tends to dip when he has time on his hand – which is quite frequently – he’s gone out of his way to make his employees feel like they’re part of a family with his endless stream of office parties, company retreats and charitable functions. Sure, he’s not the best boss by bottom-line standards, but you can bet Dunder Mifflin’s Scranton branch will miss their clueless leader once he rides off into the sunset with Holly Flax. Probably even Toby.
Gregory House (Hugh Laurie, “House M.D.”)
He will risk his own life to save the life of a patient. He will also take a knitting needle to the eye before complimenting one of his fellow doctors. Dr. Gregory House is a brilliant doctor but a pretty awful human being, so while you will get the education of a lifetime under his tutelage, the emotional scars from the experience may never heal.
Tony Soprano (James Gandolfini, “The Sopranos”)
Considering that he killed his nephew with his own hands, executed his best friend and clipped other members of his crew, you would think Tony would be a natural fit for the bad boss category. As Michael Imperioli pointed out in a recent interview with Will Harris on Bullz-Eye, Tony was a “cold-blooded criminal who, in the end, will kill his kin because, basically, he wants to keep his wagon train rolling and his money coming in.” Yet when you choose a life in the mob, aren’t these events just occupational hazards? If you think about who got whacked and who survived in Tony’s crew, there was a method to his brutality. Rats like Pussy, jerks like Ralph and flakes like Christopher had to face the music, while loyal subordinates like Silvio survived and thrived under Tony. Yet while much of the series focused on Tony as an ordinary guy in a violent business, he certainly had his quirks as well. His fainting spells and bizarre dreams led him to see a shrink, and it certainly made him an unpredictable boss as well. Anyone haunted by the images of ducks seems pretty strange to us.
Liz Lemon (Tina Fey, “30 Rock”)
Is it strange to call a woman whose name was once mistranslated as “Lesbian Yellow Sour Fruit” sexy? Absolutely, but despite her strange quirks, Liz Lemon somehow retains her sex appeal. Maybe it’s knowing that she would never judge you for the food you eat. Maybe it’s every man’s desire to meet a girl who is funny, smart, and attractive. Or maybe everyone just wants to be in bed with James Franco, even if the transitive property has to be employed to make it count. Whatever the case, work would be that much easier if every day meant reporting to a spunky middle-age brunette with the confidence to sing, “I’m a star, I’m on top, somebody bring me some ham!”
J. Jonah Jameson (J.K. Simmons, “Spider-Man”)
Bark bark bark bark bark bark bark bark bark bark! That’s J. Jonah Jameson in a nutshell, but what an amusing bark it is. Jameson and Montgomery Burns are the only characters who can wring the funny out of the words, “You’re fired.”
And, of course, we would be remiss if we didn’t include this clip, the “SNL” digital short of “Like a Boss,” from the Lonely Island’s Incredibad. Fifth of vodka…
Justin Timberlake less controversially proved himself to be, once again, no comic slouch, while promoting the charms of the co-star of his next flick, “Friends with Benefits,” the beautiful and talented Mila Kunis. Rolling Stones guitarist Keith Richards distinguished himself by simply being alive to pick up his award and being the innately humourous individual he is.
