This week’s question comes from reader Adam Schmitt:
Popular culture is full of bosses, intelligent and idiotic, supportive and demeaning. What pop culture boss would you like to work for, whether it’s because of the great personality they have or the great shenanigans you’d be able to get away with while being paid?
Alex McCown
Ever since I was a kid, I’ve thought the ideal boss would be Sam Malone. The owner-turned-employee-turned-owner of Cheers has always been the high-water mark of a great employer. He genuinely cares about his employees, he trusts everyone—even Woody—to do their jobs efficiently and capably, and when someone screws up, he’s always ready to help out and give them another chance. Plus, I’d get to be surrounded by some of the most endlessly entertaining people on the planet. The Boston bar would be a great work atmosphere, and with Malone at the helm, it would never be boring. I would relish the chance to do my part helping him try and stay one step ahead of Gary’s Old Town Tavern in the latest bar prank wars. And who wouldn’t want to start each day hearing a new Zen koan from Norm Peterson?
Erik Adams
The Wire features bosses you can look up to (Cedric Daniels), bosses you can despise (James Whiting), and bosses whose leadership skills inspire respect, even as their personal dealings incite fear (Stringer Bell). But if I could work for any citizen of the show’s densely populated Baltimore, it’d be Howard “Bunny” Colvin, a character who truly earns that “citizen” tag. I admire Colvin’s refusal to think inside the Baltimore Police Department box, even if his most radical idea—“Hamsterdam” and its fellow, War On Drugs-circumventing “free zones”—wound up getting him fired. More than once in the series, Colvin’s principles get him booted from a leadership position, but the inventive thinking and benevolent humanity behind the Hamsterdam experiment (not to mention the impact he has on the officers under his command) are the hallmarks of someone worth following no matter the workplace.
Becca James
I have to go with Phyllis Nefler from Troop Beverly Hills. I think both Rosa, her (presumably) long-time maid, and Annie Herman, her vindictively assigned assistant who later becomes a true friend, benefit greatly from her haphazard leadership. Because, sure, Phyllis can lean toward major selfishness at times, but she’s a lovely contradiction. She’ll go to bat for someone she cares about, as we see when she gives Annie a confidence-boosting makeover, showing her the sort of kindness Annie’s old boss Velda Plendor could never muster. She’s easy to pal around with as well, always busy with social engagements, her biting wit in tow, like when Annie tells her she can’t put wine in the hobo stew at the troop’s patch ceremony and she responds, “Why not? What goes better with hobos than wine?” Most importantly, for as spotlight hungry as she may seem, she’ll let you have the most memorable line, à la Rosa declaring just how bogus those patches—an extension of Velda and her Red Feathers troop’s approval—are with the iconic line, “Patches? We don’t need no stinkin’ patches.”
Marah Eakin
I thought I didn’t have an answer to this one, and then suddenly the absolute best possible answer came to me: High Fidelity’s Rob Gordon. A record store owner who’s more interested in cool vibes than clean floors, Gordon isn’t all that unlike any number of music industry people I’ve both known and worked for. Sure, he’s got his quirks, and working in a record store isn’t the most stable job in the world, even with the vinyl boom. But Gordon seems like the kind of guy who’d both pay you a fair wage and let you wear whatever you wanted to work, as long as you were into cool stuff. Isn’t that the dream?
William Hughes
I want to work for somebody who can keep their compassion in a situation that’s rapidly descending into chaos. So my vote is for Ted, the soft-spoken, well-meaning Hardbodies gym manager played by Richard Jenkins in the Coen brothers’ underrated Burn After Reading. Admittedly, part of my desire stems from the fact that Richard Jenkins seems like a really awesome guy, and I just want to hang out with him all day and be friends. But Ted’s also the only person in the entire movie who isn’t some species of self-interested, panic-prone asshole, with his only fault being his love for a completely terrible woman. And hey, when that gets him killed, maybe I can go work for J.K. Simmons’ unflappable (if less benign) CIA boss, who also seems like he’d be pretty cool to hang out with around the water cooler.
Danette Chavez
I would love to work for Leslie Knope, deputy director of the fictional Parks And Recreation department and (albeit briefly) Pawnee City Councilwoman. (I think it goes without saying that I’m referring to Knope Season 2.0 and on, but here’s the disclaimer should you need it.) Given how supportive and considerate Leslie was, it might seem like I’m taking the easy way out—who wouldn’t want a boss who would use her only vacation day to help you knock out some of your career goals? Or who saw past her employees’ apathy to help them find their passions and, in Andy’s case, a skill set? But Leslie was also well connected and exceptionally good at her job, so I would learn a lot, including how to prioritize. Yes, she was a perfectionist; but whatever she asked of others she demanded of herself tenfold. So I guess what I’m saying is, I’m not too old for a role model.
Caroline Framke
Au contraire: Ron Swanson is my Parks And Rec boss of choice. I understand that this makes me sound like someone who just doesn’t want to do work, and that’s fair, since he usually only took protégés under his wing at the Parks Department when he was sure they wouldn’t care. But as the show proved time and time again, Ron is an excellent boss when he actually gives a damn about the work. As long as he’s not being asked to contribute to whatever body of government, Ron Swanson prides himself on being a good and honest worker. He’s straightforward, aggressively fair, and unlike Leslie, he would respect your space when you need and/or deserve it. A steady stream of Leslie compliments is one way to get motivated, but personally, I’d value the hell out of a single half-smile and/or mustache twitch from Ron Fucking Swanson.
Genevieve Valentine
Brooklyn Nine-Nine’s Captain Holt. Sure, he’s not without his faults, but he admits them before disaster, which already sets him apart from 99 percent of comedy bosses. He’s an even-handed, even-tempered man with a vendetta just big enough to take up all his mental vendetta space, and it’s someone who will never be his employee, so the whole team’s in the clear. He’ll invite you over to include you but then refuse to discuss anything personal, which is the dream of every office worker who doesn’t want to get chatty. You can, with a minimum of effort, get him to begrudgingly agree to go along with anything you think might actually work—and that trust is a cornerstone of the precinct’s harmony. Plus, the 99 squad has warmed him up so much that you probably don’t even have to worry about asking how his weekend was for fear of guessing wrong. No downsides. Sign me up.
Will Harris
I have to go with Jimmy James, owner of WNYX on the late, great, never-to-be-forgotten NewsRadio. First of all, if TV has taught us nothing else (and it hasn’t), it’s that if you enjoy being in a situation where you never have any earthly idea what sort of surprises your work day may hold, then you can’t go wrong with having an eccentric billionaire as a boss. Mr. James is a guy who perpetually keeps his employees guessing, not only about who he is—he could’ve been Deep Throat, and he might also have been D.B. Cooper—but what wonderful things he might give you, whether it’s the rights to Fibber McGee and Molly in perpetuity or simply a worthwhile piece of friendly advice. In fact, there’s really only one potential downside to working for Jimmy James: He always knows how to get his way, so if you’re on the wrong side of an argument with him, you should probably just go ahead and prepare to lose.
Drew Fortune
On the surface, Homer Simpsons’s short-lived boss Hank Scorpio embodies everything one would like in a leader. As owner/president of the shadowy Globex Corporation, he values and respects his employees, running his company as a man of the people. Placing Homer in a cushy management role, the Simpsons are graced with a gorgeous house and state-of-the-art appliances. There’s zero authoritarian ego, as Scorpio is always available to talk one-on-one, whether in the midst of a fun run, or under extreme duress from the government. Despite a hectic schedule, he deftly balances work and leisure, possessing an encyclopedic knowledge of Cypress Creek’s hammock district. The only drawback is Scorpio’s sideline in world domination and cartoonish supervillainy. Even in a maniacal, homicidal state, Scorpio is quick to praise Homer for tackling super spy Mr. Bont, who Homer mistakes as a “loafer.” When Globex is eventually raided, Scorpio demonstrates superb multi-tasking, brandishing a flamethrower while dodging bullets and grenades. In the midst of this chaos, he devotes 100 percent attention to Homer, who begrudgingly resigns. Scorpio expresses genuine disappointment at the loss of his employee, and instead of a gold watch farewell, he buys Homer the Denver Broncos. We should all be so lucky.
Molly Eichel
Lutz may have once called her a name that rhymes with runt, but Liz Lemon is my ideal boss. She may seem like a mess from Jack Donaghy’s perspective, but she always kept the trains running on time despite the sheer insanity of her two stars, even though cancellation was seemingly always on the horizon (sound familiar?). She took Donaghy’s life lessons and used them (sometimes even successfully!) in her own life, yet remained her own woman enough to help her mentor when he was down. Even better? Her writers’ room had little turnaround during TGS’ run. Lemon ended her run having as close to it all as Liz Lemon could possibly have. Sure, I mainly want Tina Fey to be my boss but if Lemon is her fictional other, I’ll settle, especially because we both love cheese so much. And that whole rhymes-with-runt thing? Fey answered that best as herself: Bitches get stuff done.
Jesse Hassenger
Maybe it’s because I just re-watched it, but I think I’d enjoy working for Bobby, the theme-park boss played by Bill Hader in Adventureland. His employees seem to have a generous amount of leeway in terms of goofing off (and forming wistful summer romances, unexpected friendships, etc.), and while he takes his park job seriously, he also understands that it’s not the greatest job in the world and his employees may behave accordingly. At the same time, he’s not so clueless or negligent that you couldn’t go to him with a problem or, say, run cowering into his office when some mooks threaten to kick your ass over a rigged carnival game. Enough trust to stay relatively hands-off but enough care to go after your would-be assailants with a baseball bat? Sounds like that could work equally well in an office environment.
Tasha Robinson
For some reason, when I think of accommodating bosses, I think of Alan Arkin’s unnamed precinct captain in So I Married An Axe Murderer. He’s so endlessly supportive, caring, and reasonable that he’s willing to completely revise his personality in order to motivate his employees and give them what they need to feel comfortable in the office. Sometimes that’s a hug. Sometimes it’s a TV-cliché rant that makes them feel properly like the stars of their own show. The only downside would be the feedback sessions afterward, where I’d have to tell him whether he was going too heavy on the ethnic slurs, or mispronouncing his insults. Maybe I’d just stick with the hugs.
Caroline Siede
As a relatively squeamish person, there’s only one scenario in which I’d be interested in working in the medical field: With the advanced technology of Star Trek and under the auspicious mentorship of Dr. Beverly Crusher. The Next Gen’s personable but uber-competent doctor was a big role model for me as a kid, and as one of her assistants I’d hope to absorb even more of her scientific approach to life. Working alongside Bev in sick bay I would witness firsthand how she stays calm in a crisis, juggles multiple roles aboard the Starship Enterprise, and keeps her hair looking fantastic no matter what. Plus, since pretty much every space-born disease seems to be instantly treated with a tricorder and a hypospray, I have to imagine the job itself would be pretty easy and mercifully gore-free.
Mike Vago
Humanity may have solved a lot of its problems in the utopian 24th century of Star Trek, but there aren’t a lot of good bosses. Kirk will slap a red shirt on you and beam you down to the planet to die without even learning your name; Sisko’s a hardass who’s only interested in results; Janeway will strand you on the opposite side of the galaxy at the mercy of the franchise’s laziest writers; and of course every single admiral in the fleet is either incompetent or evil or both. So thank goodness for the best boss in the galaxy, Jean-Luc Picard. Klingon High Council wants to strip you of your honor? He’s got your back. Stuck in a malfunctioning holodeck? He’ll be the first one to put on a silly costume and come to the rescue. Need an inspiring speech projected to the cheap seats? There’s no one better. Worried about that next performance review? If he can keep Counselor Troi employed through seven years of hearing an alien warlord threaten to rip out everyone’s entrails and limit her insights to, “I sense anger, captain,” then surely your job is pretty safe.
Kayla Kumari Upadhyaya
It is probably very telling that my first thought upon reading this prompt was that I’ve always wanted Miranda Priestly to read me for filth. But upon further reflection, I came to my real answer which, it turns out, isn’t too far from my initial thought: I want to work for UnREAL’s Quinn King. Hear me out. Yes, Quinn is a terrifying boss. Yes, she probably wouldn’t hesitate to end me if I did something wrong. But I think it would be thrilling to work in such a high-stakes environment and to watch someone as masterful as Quinn do her job. And I would of course hope that our working relationship would be similar to that of Quinn and Rachel. Quinn is, to borrow a term from Nicki Minaj, a boss-ass bitch. Her last name is literally “King.” I want to work for royalty, even if we’d kill each other in the end.
Zack Handlen
I’m sure I’d regret this if it ever actually happened, but I’m going to go with newspaper editor-in-chief J. Jonah Jameson—specifically the J. Jonah played by J.K. Simmons in Sam Raimi’s Spider-Man movies. Sure, he’s a penny-pinching tyrant who spends way too much time obsessing over his plans to destroy a costumed vigilante solely because that vigilante makes him question his own moral worth, but he’s colorful and entertaining to watch, and he would give you plenty of stories to bond with your fellow journalist junkies over. Simmons’ take on the character (which remains one of the high-water marks of comic-to-screen casting choices) is weirdly charming in spite of his bullying rants, and at the very least, you’d never have to worry about being bored. About being paid, about keeping a job, and about avoiding occasional Green Goblin attacks, maybe, but not being bored.
Kate Kulzick
I’m in no hurry to return to the fabulous world of food service, but if I had to, it’s hard to think of a better boss than Bob Belcher from Bob’s Burgers. Yes, the Belcher kids cause mischief from time to time, but their restaurant-related hijinks tend to be entertaining and would make for a lively work atmosphere. Bob is passionate about food—the job would be worth taking just to try the delicious-sounding burgers of the day he comes up with—and is laid-back, yet committed to his business. He’s happy to collaborate on projects, when the need or opportunity arises, and he’s comfortable thinking outside the box. The regulars are a reliable source of interesting conversation and there are enough patrons to keep the restaurant in business, but not so many that the peak hours seem like a grind. Bob may have the occasional freak out, but he’s warm, funny, and supportive, three excellent qualities in a boss. Bob’s Burgers may not be the most glamorous place to work, but with Bob Belcher at the grill, it sure looks like a lot of fun.
Dennis Perkins
I’ve got an inconvenient need to only work at places, and for people, that I can respect, and there’s no fictional boss who fills me with the desire to serve more than Sports Night’s Isaac Jaffe, played by a never-better Robert Guillaume. As the stern yet fatherly managing editor of a group of underfunded yet principled newspeople, Isaac always fights the good fights, even after Guillaume’s real-life stroke forced series creator Aaron Sorkin to incorporate the actor’s post-recovery enfeeblement into Jaffe’s daily battles against those seeking to undermine his show’s integrity. Watching the show (still my choice for Sorkin’s best), I invariably see myself in Josh Charles’ hotheaded co-anchor Dan Rydell, who, like me, sees his job as a way to prove himself, especially to surrogate father figure Jaffe. Like Danny, I get choked up in something like worshipful awe as Jaffe—risking certain backlash from his alumni boss—gives a stirring on-air defense of a black football player refusing to play under the Confederate flag at his Southern college’s stadium in the episode “The Six Southern Gentlemen Of Tennessee.” Also like Danny, I’m certain I’d have to be periodically reminded by Isaac that hero-worship is ultimately a self-defeating trait, and that work, no matter how idealistically you commit yourself to it, is no substitute for a real life.