The Best and Worst Bosses in Pop Culture

Posted by Lauren Thoman

[TV still from The Office, NBC Universal Television]

Pop culture is full of leaders of all stripes, from starship captains, kings, and queens, to office managers and school principals. Some consistently inspire greatness, while others have turned slacking off and screwing up into an art form. Today we’ll take a look at some of the best – and worst – bosses that pop culture has to offer.


[Warner Bros Television, NBC]

Best: Leo McGarry, White House Chief of Staff, The West Wing

As President Bartlet’s right hand man, Leo ran a tight ship, surrounding himself with only the best and the brightest. An innovator and unconventional thinker, Leo didn’t let the partisan politics of D.C. run the show, always seeking out the people and programs that he believes are in the best interests of the American public. Though he wasn’t perfect, Leo inspired fierce loyalty and professional excellence in every member of his staff, and was deeply missed by both the characters and the fans when his character passed away (mirroring the real-life passing of actor John Spencer).



Worst: David Brent, General Manager, Wernham-Hogg, Slough branch, The Office

While many may be tempted to put Michael Scott on a list of worst bosses, for this one, we’re going to go with his British counterpart, David Brent. Though neither Michael nor David seemed to have much of a clue about how to run an office, Michael at least cared about his employees, most of whom seemed to view him with varying degrees of exasperated fondness. David Brent, however, never seemed to care about anyone but himself, and would go out of his way to put others down in order to build himself up. And grating personality aside, David’s managerial style didn’t ever prioritize any actual work getting done, either. No matter how you slice it, David was a pretty terrible boss.



Best: Dr. Miranda Bailey, Chief of Surgery, Grey-Sloan Memorial Hospital, Grey’s Anatomy

Introduced as a surgical resident in season 1, Miranda Bailey has worked her way up through the ranks of the former Seattle Grace Hospital, advancing to Chief Resident and eventually Chief of Surgery. In her various roles at the hospital, Dr. Bailey has demonstrated her surgical and managerial skills time and time again, while also proving herself a fierce advocate both for her staff and for the rights of her patients. While she began the series with a reputation of being harsh and unforgiving, she has since shown that beneath her occasionally prickly and demanding exterior lies a heart big enough to hold the entire hospital, and has in turn won the hearts and respect of everyone that works with her.



Worst: Michael, Chief Architect, The Good Place

Unlike some of the other ‘worst’ candidates on this list, Michael isn’t here because of an off-putting personality or nonexistent work ethic. He has an endearing personality and actually does try really hard to succeed at his professional goals, but no matter what he tries, he is just no good at his job. He can’t seem to keep his employees happy, or his carefully constructed town from crumbling (sometimes literally). Poor Michael.



Best: Leslie Knope, Deputy Director, Parks and Recreation Department of Pawnee, Parks & Recreation

Leslie is not technically the boss in her office – that honor belongs to the incomparable Ron Swanson – but effectively, she’s in charge. Leslie is the innovator and motivator for her office, and unlike Ron, whose mission in his role as Director is to never do any actual work, she is constantly taking on ambitious projects and coming up with inventive and unorthodox ways to see them through to completion. Once Leslie has set her mind on a task, she never gives up, and will endlessly persevere with a smile and an inspirational attitude. The members of her staff love her almost as much as she loves her town of Pawnee, and will follow her to the ends of the Earth… as long as they don’t have to go through Eagleton.



Worst: Douglas Reynholm, Head of Reynholm Industries, The IT Crowd

Douglas takes over Reynholm Industries despite his complete lack of qualifications after his father, Denholm Reynholm, dies and leaves the company to him. Douglas’s stint as Head kicks off with a video message from his deceased father asking him to promise never to get involved in a sexual harassment case again, and goes about as well as can be expected given that introduction. Douglas never learns what his company does or the names of his employees, is consistently sexist and misogynistic toward any women who have the misfortune of having to deal with him, and is just generally terrible at everything he tries to do.



Best: Tami Taylor, Principal, Dillon High School, Friday Night Lights

Supportive and enthusiastic, Tami always had an ear for her staff and a heart for her students. Though she was always professional, she brought her experience and empathy from her time as a guidance counselor into her role as principal, and made it clear that her first priority was always the academic and personal wellbeing of the kids at her school. Through no fault of her own, Tami wasn’t the principal of Dillon High for very long, but while she was there, she was everything a parent or teacher could want in a high school principal.


[Lionsgate Television, Netflix]

Worst: Joe Caputo, Warden, Litchfield Penitentiary, Orange is the New Black

Caputo’s worst fault isn’t that he is malicious or incompetent, but that he is complacent. In his role as Warden, Caputo is in a position to affect positive change for the inmates of Litchfield, but instead of concerning himself with the events taking place within the prison, Caputo seems more interested in personal advancement while absolving himself of any personal responsibility for the hardships faced by the inmates. Over and over, Caputo has reiterated that he sees himself as a good person whose hands are tied by the system, but the reality is that he simply doesn’t care enough to actually put himself out there, and as a result, everyone under him suffers.



Best: Jean-Luc Picard, Captain, USS Enterprise 1701-D, Star Trek: The Next Generation

As a series, Star Trek is pretty great at giving us strong, competent, thoughtful leaders, but if we had to pick just one as the cream of the crop, it would be Jean-Luc Picard – intelligent, authoritative, compassionate, and with such a deep understanding of the Prime Directive that you’d think he wrote it himself. Picard isn’t a maverick that squeezes out of dangerous situations through daring and luck, but a noble strategist, who always keeps his crew and his mission at the front of his mind. With his philosophical mind and eloquent way of speaking, Picard is the kind of captain every member of Starfleet would love to serve under.



Worst: Cersei Lannister, Queen of Westeros, Game of Thrones

Westeros has had no shortage of abysmal leaders, but Cersei may be the worst of the bunch. Always hungry for more power than her position warranted, she finally managed to claw her way onto the Iron Throne over the dead bodies of her children, who were the only people she ever genuinely and selflessly loved. Now that she’s the most powerful person in the Seven Kingdoms and has no one left to keep her in check, Cersei has made her reign one of fear, deceit, and terror. Though she still has a handful of people still loyal to her, mostly, everyone is just afraid of her, making her hold on the throne tenuous and, likely, short-lived.

Lauren Thoman

Lauren Thoman

Lauren is a writer of YA speculative fiction and a dedicated eater of queso. She lives in Middle Tennessee with her husband, two daughters, and a half-blind dog. When she’s not busy with her family, binge-watching TV shows, or writing books about dragons or superheroes, she can probably be found on Twitter, or in close proximity to coffee, tacos, or a bookstore.