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15 TV Bosses We Wish We Could Have

15 TV Bosses We Wish We Could Have

What kind of boss do we really want? Someone who inspires and challenges us to be great, or someone who brings in fresh bagels for the office and lends a sympathetic ear to hear your problems? Television has shown some great examples of fictional bosses who, even when they’re deeply flawed people, can do a lot for their employees—or at the very least, teach them a lot.

In real life, bosses can be frustrating, indifferent, clueless, irritating or even vindictive. Some can be wonderful people, of course, and even great mentors, but as employees we often wonder just why bosses do the things they do. So it’s a relief to sit down every evening to watch our favorite characters bond with—or suffer under—their own bosses. Here are a few TV bosses from series both classic and new that we wouldn’t mind working for, even if only for a short time.

15. J. Peterman, Seinfeld

via Hollywood Reporter

Wacky, weird and distracted, employees could get away with a lot as this eccentric catalog publisher wings away to remote corners of the globe on a whim, leaving hapless editor Elaine Benes to figure out the next issue without him. Peterman’s pompous verbiage stems from the sense of adventure he tries to bring back from his travels, whether he’s running with the bulls or disappearing deep into Burma to become a “white poet warlord.” On the other hand, he feels it’s critical for his editors to really understand the unique viewpoint the J Peterman catalog (based on the real J Peterman retailer) brings to its customers, even sending them on their own adventures to Tunisia, or Thailand—whether they like it or not.

14. Lorelai Gilmore, Gilmore Girls

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Teen mom-turned-hotel manager Lorelai Gilmore epitomizes the compassionate boss, managing the Independence Inn with energy and flair. Managing in a service business requires a great deal of awareness and the ability to relate to both customers and employees. In the very first episode, Lorelai rushes from behind the check-in counter to smooth out the ripples made by a rude musician, aware of the negative effect her comments could have on the hotel’s guests. But she also makes sure her employees are able to perform at their best, urging them to take time off for injuries or to get their lives in order. After the Independence Inn burns down, she ties her dream of owning her own hotel to the needs of the inn’s former employees. After raising funds by running a catering business, she buys and reopens the Dragonfly Inn with co-owner and cook Sookie St. James, bringing aboard the Independence staff.

13. Roland, The Great Indoors

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Putting aside the contrived millennials vs. GenX hijinks that underpin “The Great Indoors,” adventure writer Jack Gordon’s boss Roland repeatedly demonstrated what it takes to be a great boss in a dicey office climate during the series’ first (and maybe last) season. In one episode he zeroes in on exactly where the disconnect lies between Jack and his young writers by pinpointing to Jack’s difficulty in transitioning to a new work environment. As a retired adventurer himself, and the only person in the office closer to Jack’s age, Roland also has no problem letting down his guard after hours to go bar-hopping and share stories of his own travels to help culture-shocked Jack adjust to a new world.

12. Miranda Bailey, Grey’s Anatomy

via fanpop

Cross her, and your career is on the line. But she can also be an employee’s fiercest defender. Initially a hard-as-nails surgeon who is blunt and sometimes nasty to her interns, she matured over the series’ seasons into a more confident, relaxed leader taking on the role of chief surgeon at Sloane-Grey Memorial. She’s increasingly supportive of the other surgeons even as she balances being a mom with the demands of being a doctor.

11. Walter Skinner, The X-Files

via Screenrant

As Fox Mulder and Dana Scully’s division head, Skinner is sometimes frustrated and perplexed by the X-Files heroes as they approach him with theories and solutions that often fall far outside the purview of standard FBI practice. However, Skinner allows his agents to take a chance and go after their instincts, backing them up even if they are ultimately wrong. As a former Marine and Vietnam War combat veteran, Skinner’s experiences there helped mold him into a fair, if sometimes tough boss.

10. Dr. Richard Webber, Grey’s Anatomy

via imdb

As the former chief of surgery at Sloane-Grey Memorial, he could be tough on his staff, but was mainly known for his mentoring of surgical candidates as they entered a tough profession where mistakes could easily be deadly. Throughout his time at the hospital he took advantage of every teachable moment that he could, even leveraging his own serious illness to help interns learn how to diagnose hard-to-discern conditions. Despite the many stresses involved in the job, he was always a patient figure ready to impart pearls of wisdom to the younger doctors working with him.

9. Lou Grant, The Mary Tyler Moore Show

via imdb

Mary Richards’ grumpy and tough boss on the Mary Tyler Moore Show, Grant is still held up as the prime example of a great TV boss. Ed Asner’s gruff character was popular enough to earn his own spinoff sitcom. Grant’s assessment of his reporters’ work tends to be blunt and to the point, and he refuses to back down from an opinion. “Take this bilge Corrine wrote and make it sound like news,” he tells Hal in one episode. While he embodied the straight-talking, hard-drinking beat reporters of the last century, once quipping, “Anything goes with cognac,” he also had a deep love for his profession. His conversational clap-backs tended to reflect his frustration at his TV station’s flaws, his reporters’ mild ineptitude, and the problems of the journalistic profession in general.

8. Don Draper, Mad Men

via imdb

When he wasn’t busy chugging martinis or chasing yet another woman, Don Draper had an eye for spotting and nurturing the potential in others from time to time. And he never shied away from calling BS whenever he spotted it too. His biggest beneficiary was Peggy, who was promoted up from an administrative position and grew over time to a leadership role at the ad agency. On the flip side, Draper has some massive character flaws, outright stealing an award-winning idea from Peggy, which caused her to quit and move to a rival agency. He’s also an unrepentant womanizer and a barely functional alcoholic. At the same time he’s a genius at creating ads that sell products, and his guidance, though it tends to be blunt, is often on point. “Endorsements are lazy,” he says in one episode when his writers float the idea of using pro football player Joe Namath to endorse a client’s product, forcing them to start over. He might be hell to work for, but his employees will come out the other side smarter and tougher for the experience—a requirement for working at ad agencies in the 1960s, and today.

7. Jean-Luc Picard, Star Trek: The Next Generation

via imdb

The ultimate space boss, every Trekker wished they could work for this Earl Grey-swilling classical music aficionado. Picard normally delegates work to his subordinates, but isn’t above doing the work himself now and then. He’s also concerned about his crew’s professional development, schooling them occasionally on the nuances of being a Starfleet officer—once chastising a young ensign for mistakes she made while a cadet in order to see how she would deal with unfair treatment. Ever fair-minded, willing to listen to employees’ problems and concerns, Jean-Luc makes almost-always foolproof decisions that keep everyone happy. Yes, it’s a fantasy, but after a rough day of being treated unfairly by a real boss, having a cuppa with this captain is worth dreaming about.

6. Red Reznikov, Orange Is The New Black

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Ruling the prison kitchen in Orange Is The New Black, Galina “Red” Reznikov serves up a steely resolve with every spoonful—and occasionally, some tough love. Her helpers are hand-picked, and her rules are ironclad: No drugs, no alcohol, no sleeping with the guards. A former restaurant owner, Red has the skills and knowledge to get the most out of the flavorless and processed dreck that passes for food in prison. She’s also able to compromise when necessary, such as with her biggest rival and onetime kitchen leader Gloria, allowing some of her helpers to stay with the kitchen crew after Gloria leaves.

5. Roger Sterling, Mad Men

via imdb

Far less inclined than Don to steal your great idea, hard-drinking Roger Sterling is everything Draper ever wanted to be—a wealthy adventurer who inherited one of New York’s top ad agencies, with a quip for everything and a different girlfriend seemingly every week. Sterling’s laid-back style is simply window dressing that hides a hardworking achiever with genuine talent for his job. As an executive-level boss, he sets the example for his agency employees in how they should dress, talk, and act—and he takes it very seriously, even if he’s not always happy with the ethical grinding house that is the advertising industry. “You know, we sold actual death for 25 years with Lucky Strike. You know how we did it? We ignored it,” he says in season 6.

4. Louis Huang, Fresh Off The Boat

via imdb

His wife rules the roost at home, but inside the Cattleman’s Ranch steakhouse, Louis is the boss. Benevolent though sometimes exasperated with his workers’ escapades—his manager’s constant flakiness due to implied drug use, and his head waitress, who’s kind of a head case—he steadily brought his restaurant into profitability as the series rolled through its third season. A recent episode highlighted the nice-guy approach he takes to leadership, when he and his wife made a bet to see who can best train their sons to play golf like Tiger Woods. Oldest son Eddie levels up quickly thanks to a pre-training bribe of Cinnabons from his dad, while youngest son Evan balks at Jessica’s tiger-mom tactics. While the episode points out that it’s important to balance benevolent leadership with strong discipline, we all know which boss we’d rather have. It’s the one with the free Cinnabons.

3. Ray Holt, Brooklyn Nine-Nine

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Buttoned-down Ray Holt is a take-no-crap police captain saddled with managing the juvenile antics of Detective Jake Peralta. While he could easily be a simple foil for Peralta to prove just how brilliant he is at solving crimes while thumbing his nose at the establishment—early on, the young detective battles his new captain over a dress-code requirement to wear a tie, for example—Holt shows he’s much more complex, and that he’s the perfect chief for the job. As a mid-level boss he has to balance keeping his detectives in line and on point solving crimes, while protecting them as much as possible from the whims of higher-ups like Madeline Wuntch, who tries to undermine his authority every chance she gets.

2. Jack Donaghy, 30 Rock

via rebloggy

Despite seeming buffoonish and slightly out of touch with 30 Rock’s creatives, he’s actually a rags-to-riches exec who has never forgotten his own roots in South Boston. While attending Princeton on an “Amory Blaine Handsomeness Scholarship,” Jack worked several minimum-wage jobs including “the day shift at a graveyard, and the graveyard shift for the Days Inn.” That background plays its part in the gestures he makes toward his underlings, including making Liz Lemon his reluctant protege. He’s not without flaws, including an almost unswerving devotion to capitalism, but occasionally shows a human side—refusing to fire Kenneth Parcell after the NBC page bets his job in a poker game, for example. And every once in awhile, he’ll fire a backhanded compliment at one of his employees when they go above and beyond in his eyes.

1. Phil Coulson, Agents of S.H.I.E.L.D.

via imdb

This S.H.I.E.L.D. team special agent is the kind of person you’d hang out with after work, if he wasn’t the boss. He’s a huge fan of the Avengers, Captain America, and superheroes in general, making for a great conversationalist if you’re into the same thing. As a veteran S.H.I.E.L.D. operative and Nick Fury’s former second in command, Coulson brings his own credibility to his leadership role. But he’s also a genuinely nice guy—not always the makings of a great boss, but in this case he leads the S.H.I.E.L.D. team from the front, refusing to delegate the hard tasks to others. That kind of genuineness inspires a lot of loyalty from his team.


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