November 4, 2024 | Peter Kinney

The Worst Bosses In Television History (And Some Of The Best)


There's A Thin Line Between Love And Hate

TV has shown us every type of boss—loveable leaders to tyrannical terrors to those who fall in between. Here's a list of characters who make you shout, "I quit!" or "I wanna be you!"

Office - Star Trek

Dr. Miranda Bailey: Grey's Anatomy  

Dr. Miranda Bailey is a strong boss. She always wants her team to do well, but she can sometimes go a little bit extreme to make sure they achieve that. Some people label her overly strict because she is always very serious, while deep down, she is just doing her job. 

Dr. Miranda Bailey: Grey's Anatomy  Bailey Lays Down New Ground Rules - Grey's Anatomy by ABC

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Dr. Miranda Bailey: Grey's Anatomy (Cont.)

Even with the strict rules, Dr. Miranda always wants to help when things get tough, which shows that she wants the best for them. The time she stayed with Cristina Yang after her surgery showed how much she cares about her team and is willing to see them to health.

Dr. Miranda Bailey: Grey's AnatomyBailey Meets Jordan, a Resident Who Wants to Learn From Her - Grey's Anatomy by ABC

Dr. Miranda Bailey: Grey's Anatomy (Cont.)

As Chief of Surgery, she shows that women can do great things in medicine. Her rise from a hard-working resident to a respected boss shows her hard work and talent. Bailey is a role model for women who want to lead and succeed in their careers.

Dr. Miranda Bailey: Grey's Anatomymiranda bailey being iconic for almost 6 minutes straight. by Esqua

Diane Lockhart: The Good Fight 

Diane Lockhart stands out as a boss who is unapologetically feminist. She is always working hard to support women, making her law firm a place where they feel empowered. Her efforts push her female coworkers to do well and help them feel respected at work.

Diane Lockhart: The Good Fight Diane Lockhart - The Storm By The Good Fight Fanpage

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Diane Lockhart: The Good Fight (Cont.)

So when Alicia Florrick needed help, it was no surprise Diane went all out for her, even though she had her doubts. By helping and guiding her, Diane shows she's a great leader. She wants her team to do well and improve. 

Diane Lockhart: The Good FightBest of Diane Lockhart (Christine Baranski) - The Good Fight - season 2, episode 1 by The Good Fight Fanpage

Diane Lockhart: The Good Fight (Cont.)

The unfortunate twist of Diana facing big problems like losing her money in a Ponzi scheme impacted both her work and life, which also made the plot more interesting. Despite these challenging times, she stayed strong and adjusted to the situation. 

Diane Lockhart: The Good FightDiane Lockhart [The Good Wife] - We follow the law [5x04] by Supsi

Buddy Ackerman: Swimming With Sharks

The boss that literally nobody wants to have anything to do with is Buddy Ackerman. He's harsh and cusses at his assistant, Guy. But that's not all—instead of helping him, Buddy treats Guy like he doesn't matter. Talk about a more toxic work environment.

Buddy Ackerman: Swimming With SharksYou Have No Brain - Swimming with Sharks (1994) by Görkem Uyar

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Buddy Ackerman: Swimming With Sharks (Cont.)

Such abusive behavior leads to serious problems for himself and those around him. Overwhelmed by Buddy's bad treatment, Guy struggles to keep his friends. His girlfriend, Dawn, tries to help him, but she gets pulled into the problems, too. 

Buddy Ackerman: Swimming With SharksSwimming with Sharks by Christian Anthony C

Buddy Ackerman: Swimming With Sharks (Cont.)

In the end, the workers are always at a disadvantage because of the bad choices their bosses make. Buddy's cruel words and actions don't just hurt their work; they seep into their personal lives, which makes everyone around him unhappy.

Buddy Ackerman: Swimming With Sharks (Cont.)Swimming with Sharks by Christian Anthony C

Angela Bower: Who's The Boss?

In Who's the Boss?, Angela Bower is a strong and kind boss who runs her own ad company. She is always all out to show that women can do well in business and still be nice. And her decisions are always ones to be proud of.

Angela Bower: Who's The Boss?Angela Gets Fired! | Who's The Boss? by Throw Back TV

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Angela Bower: Who's The Boss? (Cont.)

The surprising change between Angela and Tony the housekeeper was one of the best parts of Who's the Boss?. Angela was the successful boss, while Tony took care of the home and the kids, something not often shown on TV. This switch challenged old ideas about gender roles.

Angela Bower: Who's The Boss?Angela's Ex Husband Fights For Custody | Who's The Boss? by Throw Back TV

Angela Bower: Who's The Boss? (Cont.)

Angela Bower was a special character because she was a woman in leadership during the 1980s. As a successful ad boss, she broke gendered norms about what women could do. The people who made the show wanted to change things up, showing how Angela was strong but also soft and caring.

Angela Bower Who's The Boss (Cont.)Who's The Boss? | Angela Finds The Perfect Man! | Throw Back TV by Throw Back TV

Michael Scott: The Office

As the boss at Dunder Mifflin in Scranton, Michael Scott has a special and friendly way of leading. He tries to be friends with his workers instead of being all business, which makes the workplace feel like a family. He also enjoys planning fun events, like parties and outings.

Michael Scott The OfficeMichael Scott Moments that need to be discussed - The Office US by The Office

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Michael Scott: The Office (Cont.)

Sometimes, Michael makes a decision that makes you question everything about him. For example, he buys a $400 iPod for Secret Santa, which is way more than the budget that they talked about. Still, he always managed to make everyone in the office feel valued (except Toby Flenderson, of course).

Michael Scott The Office (Cont.)the office moments that are cringier than scott's tots | Comedy Bites by Comedy Bites

Michael Scott: The Office (Cont.)

Even with his many mistakes, Michael shows surprising kindness and understanding that positively affect his employees. One instance is in the episode Business School, where he cheers on Pam by going to her art show and being truly proud of her work.

Michael Scott The Office (Cont.)-2UNDERRATED Cold Opens that make me audibly burst out laughing - The Office US by The Office

Jessica Pearson: Suits

Jessica is confident, resourceful, and doesn't shy away from making tough choices. One time, when her law firm was about to lose a big client, she made a quick plan and called a team meeting. She gave everyone jobs to keep them focused and excited.

Jessica Pearson: SuitsJessica Pearson Needs 2 Million Dollars | Suits by Suits Official

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Jessica Pearson: Suits (Cont.)

In the show, Jessica Pearson fights to get her law firm back from her ex-husband, Jeff Malone. She puts in a lot of effort and plans carefully to outsmart him. By working with her team and using her smarts, Jessica wins back her job. 

Jessica Pearson: SuitsJessica needs to chose between love and work | Suits by Suits Official

Jessica Pearson: Suits (Cont.)

As a boss, Jessica works hard to do what is right for her clients and her team. When everyone found out that Mike Ross wasn't really a lawyer, she took the blame and risked her OWN job to help and protect him. 

Jessica Pearson: SuitsJessica needs to chose between love and work | Suits by Suits Official

Arthur Carlson: WKRP In Cincinnati

Arthur Carlson, also known as "The Big Guy," is the boss at WKRP. He has trouble being a strong leader and doesn't understand the new music styles, and instead of learning what's new, he often plays with toys in his office.

Arthur Carlson WKRP In CincinnatiThe Art of Being The Big Guy with a tribute to WKRP regulars no longer with us. by JJ's Place

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Arthur Carlson: WKRP In Cincinnati (Cont.)

Even though Arthur isn't great at his job, he knows what is right and wrong. In one case, he stands up to a lousy photographer who took pictures of an employee without permission. And even though he makes mistakes, Arthur shows that he will protect his workers when it really matters.

Arthur Carlson: WKRP In CincinnatiWKRP Arthur Carlson by Dave K

Arthur Carlson: WKRP In Cincinnati (Cont.)

His low-key, friendly approach helps employees like Herb tackle their struggles, such as alcoholism. In episodes like Who is Gordon Sims, he assists Venus in dealing with his past. He basically acts like a father to his workers. 

Arthur Carlson Wkrp In Cincinnati (Cont.)WKRP Arthur Carlson by Dave K

Jack Donaghy: 30 Rock

Jack is a mixed bag with quite a few tricks up his sleeve. On one occasion, he helped create the Trivection oven, which shows he can see great ideas in unexpected places. He also encourages his workers to think differently, especially with Liz Lemon.

Jack Donaghy: 30 RockJack Plays Colonizers of Malaar | 30 Rock by

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Jack Donaghy: 30 Rock (Cont.)

On the other hand, Jack is a ruthless corporate man with a self-serving nature, which makes him hard to deal with. He prioritizes corporate interests over personal relationships and makes ruthless decisions that negatively impact his employees.

Jack Donaghy: 30 Rock30 Rock - Jack's Message (Episode Highlight) by 30 Rock Official

Jack Donaghy: 30 Rock (Cont.)

Still, his loyalty to his team shows when he fights for their jobs and future, which is commendable. He solves hard problems, such as keeping NBC safe from other companies. By helping his team feel safe and strong, he proves he is a leader you can trust.

Jack Donaghy: 30 RockJack Donaghy's Best Negotiations | 30 Rock by 30 Rock Official

Jean-Luc Picard: Star Trek

Picard showed excellent leadership because he cared about his team. He made calm and smart choices that helped his crew trust him. In The Inner Light, for example, he helped his crew feel close by letting them talk about their feelings and support each other.

Jean-Luc Picard Star TrekDL 2: Sir Patrick Stewart aka Captain Jean-Luc Picard - Trek Nation Director's Log - EXCLUSIVE by TrekNation

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Jean-Luc Picard: Star Trek (Cont.)

Jean-Luc Picard helps his crew grow as leaders. He encourages them to try new things and supports them with personal problems. His friendship with Data is a great example of this. Picard helps Data learn about being human while still allowing him to be his true self.

Jean-Luc Picard Star Trek (Cont.)Star Trek: 10 Things You Didn't Know About Jean-Luc Picard by TrekCulture

Jean-Luc Picard: Star Trek (Cont.)

The USS Enterprise, led by Jean, has good values and rules. The captain wants everyone to share their ideas and listen to them so everyone feels special and involved. In the episode The Best of Both Worlds, everyone was encouraged to speak up about their problems.

Jean-Luc Picard Star Trek (Cont.)-2The Best Decisions Captain Picard Has Ever Made In Star Trek by Looper

Miranda Priestly: The Devil Wears Prada

Miranda Priestly will make you rethink your own ethics and values. Some call her the worst boss, but others might say that she pushes everyone to reach their true potential. People around her were almost always tense about meeting her big demands to avoid landing in big trouble. 

Miranda Priestly: The Devil Wears PradaTop 10 Most Epic Miranda Priestly Moments by MsMojo

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Miranda Priestly: The Devil Wears Prada (Cont.)

Her way of leading is very controlling. She seems bossy because she wants everything to be perfect. Her strong attitude helps her workers be good at their jobs, but sometimes it is too much. For example, she asks a lot from Andy, which some people think is not healthy.

Miranda Priestly: The Devil Wears Prada In Defense Of: The Devil Wears Prada's Miranda Priestly by MsMojo

Miranda Priestly: The Devil Wears Prada (Cont.)

She is a well-known person in pop culture, famous for her aura and strong attitude. Her sharp words make her a character that will not be easily forgotten. Even after the movie, her influence is still there.

Miranda Priestly: The Devil Wears PradaThe Devil Wears Prada | Miranda's Most Savage Moments | 20th Century FOX by 20th Century Studios

Dave Harken: The Horrible Bosses

Nick is a worker who feels frustrated. Why? His boss, Dave Harken, is manipulative and often talks about giving Nick a promotion but never does. Harken's selfish actions show a controlling boss no one loves—staying true to the show's name.

Dave Harken: The Horrible BossesHorrible Bosses/Best scene/Seth Gordon/Jason Bateman/Charlie Day/Jason Sudeikis/Kevin Spacey by Eli D

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Dr. Julia: The Horrible Bosses

Another boss in this series to be wary of is Dr. Julia Harris, who creates an uncomfortable workspace filled with hateful behavior. She pressures her employee, Dale, to have a sexual relationship with her and threatens to tell his fiancée if he doesn't. 

Dr. Julia: The Horrible BossesJennifer Aniston as Dr. Julia Harris IN🎬Horrible Bosses (2011)🎥Directed by Seth Gordon [HQ] by Cinema History

Bobby Pellit: The Horrible Bosses

When Bobby Pellit's father dies, he takes over as boss, and things get messy. He is not careful and uses drugs, which makes work feel scary and leaves workers worried. It's like every boss in the series is trying to top the other to be the most horrible one.

Bobby Pellit: The Horrible BossesHorrible Bosses (Unrated) - I'm Your Boss Now - HD by JustPressPlay

Tony Soprano: The Sopranos 

As the leader of the DiMeo mob family Tony Soprano was well known. This character has to handle the tough things about being in the mafia and also problems at home, which makes him strict and scary. Some people think he is clever, while others are afraid.

Tony Soprano: The Sopranos Tony Soprano and Dr. Melfi S1-3 (Compilation) - The Sopranos by ceerious

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Tony Soprano: The Sopranos (Cont.)

Tony always uses tricks and threats to get what he wants. For example, he kills his cousin Tony Blundetto to stop other gangs from getting back at him. His actions show that he cares about keeping his family safe but not about family bonds. Anyone else getting Klaus Mikealson flashbacks?

Tony Soprano: The SopranosThe Sopranos - Tony Dreams by ceerious

Tony Soprano: The Sopranos (Cont.)

Besides using physical violence, he uses guilt and emotional pressure to control people. His complicated relationship with Christopher Moltisanti shows this well. After a car accident, he suffocated Christopher, showing that his choices are often affected by personal feelings but still lead to very harsh results.

Tony Soprano: The SopranosThe Sopranos - Tony Dreams by ceerious

Margaret Tate: The Proposal

Using fear, Margaret Tate forces her assistant, Andrew, into a fake marriage just to keep her job. She only cares about herself and doesn't think about how it might be an inconvenience to him. She consistently puts her own needs above Andrew's feelings and happiness.

Margaret Tate: The Proposal(The Proposal) Margaret & Andrew • I think I'm in love by NiceDhampir

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Margaret Tate: The Proposal (Cont.)

Her constant pressure makes it hard for Andrew to keep his work and personal life separate. She controls his career choices, which prevents him from following his own goals. Andrew, caught in a stressful work environment, watches his dreams slip away as Margaret focuses solely on her own needs.

Margaret Tate: The ProposalMargaret Tate & Andrew Paxton (The Proposal) by 129Ashley129

Margaret Tate: The Proposal (Cont.)

She is so busy trying to save herself that she doesn't notice the harm she causes to others and herself. She feels isolated, especially after losing her family. This loneliness and unhappiness blind her to the damage her poor leadership causes—not just to her workers but also to her own well-being.

Margaret Tate: The ProposalMargaret Tate & Andrew Paxton (The Proposal) by 129Ashley129

Lyle: The Internship

Instead of being a good leader, Lyle tries too hard to be cool, which makes things difficult for his team. His strong need to fit in makes it really hard for his team to know what to do, and they struggle to follow clear directions from him.

Lyle: The InternshipTHE INTERNSHIP | Featurette: Meet The Nooglers by 20th Century Studios Philippines

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Graham: The Internship

Another boss in this series who only cares more about himself is Graham. He cheats during a competition to get ahead, which makes the team doubt him. By thinking only of his own success and not what's right, he creates a bad working environment. 

Graham: The InternshipThe Internship 2013 - So Fat by AchuCKR

Lyle and Graham: The Internship (Cont.)

The bosses in The Internship make it very hard for people to improve. Billy and Nick want to do well, but Lyle and Graham always need help to get through. Billy even leaves for a little while because he feels sad about the poor leadership.

Lyle and Graham: The InternshipThe Internship Interview with Josh Brener by Flicks And The City Clips and Internship Graham Clip by Englishtongan01

Steve Jobs: Steve Jobs

With very high standards for himself. Steve Jobs led by mixing creativity with strict rules. This helped Apple become a top tech company. However, many think his way of working was difficult to keep up with, while some liked how he wanted to do things right.

Steve Jobs: Steve JobsSteve Jobs - Official Trailer | Danny Boyle | Michael Fassbender | 2015 by Universal Pictures UK

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Steve Jobs: Steve Jobs (Cont.) 

Jobs had big ideas that changed the world, like the iMac and iPhone. His push for success made great products but also practically saw the end of some of his relationships. He often put work before everything else, even family.

Steve Jobs: Steve JobsSteve Jobs - Official Trailer (HD) by Universal Pictures

Steve Jobs: Steve Jobs (Cont.)

His need to be perfect made people wonder what he really wanted. Jobs' ideas, like the iPhone, changed the world, but his focus on work caused tension. Still, his smart ideas made people respect him, even though some were scared of him.

Steve Jobs: Steve Jobs Steve Jobs - Official Trailer (HD) by  Universal Pictures


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