Most Memorable TV Bosses From 'The Office' to 'The Bold Type'

From the inspiring to the inept, these bosses made their mark on TV history.
by Allison Bowsher — 

From left to right: Steve Carell in 'The Office' and Melora Hardin in 'The Bold Type'


It's been five years sinceThe Bold Type entered the TV landscape on June 20, 2017. The Freeform series made fast work of cementing itself as a series that puts female friendships first, quickly drawing comparisons to Sex and the City

Starring Katie StevensAisha Dee, and Meghann Fahy as Jane, Kat, and Sutton, The Bold Type centers on three best friends living in New York and enjoying their dream careers at the fictional Scarlet Magazine. The show follows the trio as they lift each other up through professional and personal hardships. Much of their success at Scarlet is not only because the women have the support of their friends, but also because they have the support of their boss, Scarlet editor-in-chief Jacqueline Carlyle (Melora Hardin).

Memorable TV bosses tend to fall into three categories: the terrifying, the incompetent, and the inspiring. Jacqueline undoubtedly lands in the last category, although Hardin has displayed her range by also dipping her toe in the first category in her role as Jan Levinson on The Office.

As Jacqueline, viewers are treated to a boss who champions her staff in their professional endeavors and provides counsel when they need it in their personal lives. How many bosses are willing to bail their employees out of jail?

Jacqueline's approachability, her seemingly endless supply of understanding, and her knack for knowing when her employees need a hug makes her a boss who is almost too good to be true. It also makes her one of TV's most memorable bosses.

From the warm and welcoming to the frigid and frightening, here are some of TV's most memorable bosses, ranked by the Metascore of the series on which they appear.


'The Sopranos'


Tony Soprano (James Gandolfini)

The Sopranos (Metascore: 94)
Best for: Fans of mobster shows and in-depth character development
Where to watch:

, Google Play, , iTunes,
Seasons: 6

It's not uncommon for employees to have some fear of their bosses, the person who can deny their vacation request or decide they don't deserve a raise. But for the people who work for Tony Soprano, the term "my boss is going to kill me" is literal. Throughout six seasons of The Sopranos, Tony rises in the ranks to become the head of a large New Jersey crime family. This position requires him to balance his work life, which often involves killing people — including members of his own family — with his home life, which includes a strained relationship with his wife (played by Edie Falco) and kids. Mental health support in the workplace is important and while Tony isn't giving employees time off to deal with their anxiety or depression, he does see a therapist himself (Lorraine Bracco). Frequently included on best TV shows of all time lists, The Sopranos won several awards during its run, including three Emmys and one Golden Globe for Gandolfini's performance as a boss who was both terrifying and memorable.

"The series became an instant TV landmark because of its riveting stories, wonderfully drawn characters, superb acting and intelligent direction." — Barry Garron, The Hollywood Reporter


Julia Louis-Dreyfus in 'Veep'


Selina Meyer (Julia Louis-Dreyfus)

Veep (Metascore: 82)
Best for: Fans of fast-paced comedies with a political edge
Where to watch:

, Google Play, , iTunes,
Seasons: 7

Louis-Dreyfus is so, so good at being a bad, bad boss theSeinfeld alum made history by winning six consecutive Emmys for her Veep role. As Selina Meyer, the Vice President of the United States, Louis-Dreyfus has mastered the art of the takedown, with her cutting commentary and biting criticism equally doled out between her political competitors and her loyal staff. There's very little said by Selina that would be deemed politically correct, including how she speaks to her staff, most of whom can also hold their own when it comes to creatively vulgar character assassinations.

"The series reserves its most blistering humor for the universal narcissism on display, always distracting from the real work at hand." — Matt Brennan, Slant


Constance Zimmer in 'UnReal'


Quinn King (Constance Zimmer)

UnReal (Metascore: 78)
Best for: Reality dating show fans who want to see behind the curtain
Where to watch:

, Google Play, , iTunes, Tubi,
Seasons: 4

Pitting producers against each other, blackmailing studio heads, and drawing tears from everyone around her, including the show's star, is a typical day for Everlasting executive producer Quinn King, who makes a successful series about love by throwing ethics out the door. As the leader of Everlasting, a Bachelor-type series within UnReal, Quinn is the puppet master who has a hand in controlling every aspect of production, from what contestants wear, to who they sleep with. If there's an HR rep on Everlasting, they're definitely not doing their job.

"Often uncomfortable to watch, sometimes hilarious soap opera, UnREAL is also both intelligent and thought-provoking, one of TV's smartest and most cynical shows." — Gail Pennington, St. Louis Post-Dispatch


John C. McGinley in 'Scrubs'


Dr. Perry Cox (John C. McGinley)

Scrubs (Metascore: 74)
Best for: Fans of comedies that can also tug at heartstrings and have no shortage of (mostly lighthearted) teasing
Where to watch:

, fuboTV, Google Play, , iTunes,
Seasons: 9

Although Dr. Bob Kelso (Ken Jenkins) is the Chief of Medicine at Sacred Heart Hospital and a memorable boss in his own right, it's Dr. Perry Cox who earns a spot on our list thanks to his seemingly endless supply of cutting one-liners and female names for his male residents, specifically Dr. John "J.D." Dorian (Zach Braff). Dr. Cox's method of teaching isn't always by the book and often includes forms of public embarrassment for the young doctors under his care, but is problematic in hindsight. But he also uses his authority to guide the residents and help them become better doctors by providing small pockets of emotional support, including in the series premiere when he gives J.D. the encouragement he needs to insert his first chest tube.

"Scrubs is to the average sitcom as a steak at the Palm is to a Big Mac. We are talking an entirely different, and superior, species." — Tom Shales, The Washington Post


Alec Baldwin in '30 Rock'


Jack Donaghy (Alec Baldwin)

30 Rock (Metascore: 73)
Best for: Fans of workplace comedies that take real-life inspiration (in this case, Saturday Night Live)
Where to watch:

, Google Play, , iTunes, Netflix, ,
Seasons: 7

As a network executive with little experience in how to run a comedy show, Jack Donaghy often creates more problems for TGS With Tracy Jordan showrunner Liz Lemon (Tina Fey) than he fixes. His eerily calm, whisper-like proclamations often land somewhere between oversharing and soul-crushing, like the time he told Liz she had was the "sexual equivalent of a million Hindenburgs." Jack's demands on Liz to ensure her series is a success typically leave her anxious and scrambling, with little to no help from her cast, which includes Tracy Jordan (Tracy Morgan) and Jenna Maroney (Jane Krakowski). For his performance as a stress-inducing boss, Baldwin took home three Golden Globes and one Emmy.

"One of the zaniest — and most savvy — workplace comedies in years." — David Zurawik, Baltimore Sun


From left to right: Andy Samberg and Andre Braugher in 'Brooklyn Nine-Nine'


Raymond Holt (Andre Braugher)

Brooklyn Nine-Nine (Metascore: 73)
Best for: Comedy fans who enjoy kooky characters and semi-realistic settings
Where to watch:

, fuboTV, Google Play, , iTunes, , Seasons: 8

A boss doesn't have to be warm and fuzzy to lead with compassion and care, as evidenced by Captain Raymond Holt. As the leader of the 99th division of the Brooklyn Police Department, Captain Holt is tasked with helping his detectives solve crimes and keep the city's residents safe. An inspiring leader who is better known for his impeccable grammar than his outward displays of affection, Captain Holt is much more than just a boss to his detectives, also acting as a mentor, a father figure, and an ally.*

"The strength of Brooklyn Nine-Nine is in the way it summons the communal spirit of [Parks and Recreation, The Office, and 30 Rock] to not only poke fun at crime-show clichés, but also reinterpret them with a fresh and idiosyncratic comedic point of view." — Luis Sanchez, Slant


Amy Poehler in 'Parks and Recreation'


Leslie Knope (Amy Poehler)

Parks and Recreation (Metascore: 67)
Best for: Viewers who want a feel-good comedy with plenty of callbacks in each season
Where to watch:

, fuboTV, Google Play, iTunes, ,
Seasons: 7

If every town and city had a Parks and Recreation department with a boss that was as committed and enthusiastic for their job as Leslie Knope, the world would be a prettier, healthier place. An ardent supporter of her hometown of Pawnee, Ind., Leslie spends her days trying to hype up her employees, motivating and encouraging them to do whatever they can to improve their small town and themselves. Her seemingly never-ending supply of energy and penchant for organizing (so many binders) eventually results in a career in politics, where she continues to be a boss that leads by example, even if where she's leading her team is very, very slippery.

"It consistently pokes fun at our culture and foibles in ways that are clever and sometimes sharp but never mean." — Nancy DeWolf Smith, The Wall Street Journal


Steve Carell in 'The Office'


Michael Scott (Steve Carell)

The Office (Metascore: 66)
Best for: Mockumentary fans who can handle a character that is very good at making people very uncomfortable
Where to watch:

, Google Play, iTunes, ,
Seasons: 9

The self-proclaimed "World's Best Boss" (he bought his own mug at Spencer Gifts), Dunder Mifflin Paper Company regional manager Michael Scott doesn't always do the right thing in front of his employees. Okay, he rarely does the right thing. His frequent missteps, including racially and sexually insensitive remarks, as well as outright hostility towards one employee in particular, make him a boss that often frustrates employees, even causing them life-threatening levels of stress. But even though his own immaturity often shines through, it would be tough to find a boss that loves Dunder Mifflin and his employees more, and all of that adds up to a prime spot on this list.

"The Office is a daring, unflinching take on very American workplace tensions." — James Poniewozik, Time


James Pickens Jr. in 'Grey's Anatomy'


Dr. Richard Webber (James Pickens, Jr.)

Grey's Anatomy (Metascore: 64)
Best for: Fans of medical dramas who are ready to invest their viewing time in one of the longest-running series ever
Where to watch:

, fuboTV, Google Play, , iTunes, Netflix,
Seasons: 18 (so far)

There are many great doctors walking the halls of Grey Sloan Memorial Hospital, but few can boast the same carrier longevity as Dr. Richard Webber. First as the Chief of Surgery and later as a General Surgery Attending, Dr. Webber uses his experience and position to guide both new doctors and his peers. An imperfect character, Webber has dealt with his own demons, including affairs and alcoholism, and has used his experiences to connect with his staff and, at times, protect them. As one of only three of the original characters still starring in Grey's Anatomy, Dr. Webber continues to teach new doctors, eventually becoming the head of the residency program.

"Grey's wants to offer something for everyone, it seems, and does an admirable job not only of mixing drama, comedy and romance, but also of mixing in issues of today's complicated world of science." — Chuck Ulie, Chicago Sun Times


Melora Hardin in 'The Bold Type'


Jacqueline Carlyle (Melora Hardin)

The Bold Type (Metascore: 58)
Best for: Drama fans who want glitz, heart, and strong leading ladies
Where to watch:

, Google Play, , iTunes,
Seasons: 5

The Bold Type celebrates female friendship with its three leading characters, who work together at Scarlet Magazine. One of the reasons the friendship between the three women thrives not only outside office hours but also inside their media workplace, a notoriously competitive landscape, is because of the supportive environment that has been created by editor-in-chief Jacqueline Carlyle. She encourages her employees to follow their instinct and to work as a team. She is willing to go to bat for them even when she receives pushback from the higher-ups. Plus, her character left a fashionable mark on TV and gives #fitnessgoals thanks to her impressive ability to run a magazine while walking on a treadmill in stilettos.

"It's part journalism drama, part Sex and the City-style female bonding comedy with sex and romance; it's equally interested in being both things at once, to the best of its ability, and damned if it doesn't pull it off more often than you'd think." — Matt Zoller Seitz, Vulture