From the empathetic mentors who guide us to success to the bad figures who make every day a living nightmare, these fictional leaders offer a spectrum of management styles we’d either aspire to work for or run from in terror. Their unique personalities, for better or worse, provide compelling lessons on power dynamics.
Leslie Knope – Parks and Recreation
As Deputy Director of the Parks Department in Pawnee, Leslie Knope is the kind of boss who inspires loyalty and passion. Tirelessly optimistic and relentlessly supportive, she champions her team with boundless enthusiasm. While her perfectionist streak can be intense, her belief in good governance and waffles would make her an absolute delight to work for.
Don Draper – Mad Men
Don Draper’s charisma and creativity made him a powerhouse in the 1960s advertising world, but his personal demons and emotional detachment would make him a complex boss. He values talent and bold ideas but can be moody, unreliable, and at times deeply aloof.
Michael Scott – The Office
Michael Scott may not be the most competent manager, but he’s certainly one of the most unforgettable. As Regional Manager of Dunder Mifflin’s Scranton branch, his cringe-worthy antics are often offset by genuine, if misguided, efforts to care for his employees. His lack of professionalism would be exhausting in real life, but his heart (and comedic timing) make him a boss viewers can’t help but root for.
Olivia Pope – Scandal
As the head of a crisis management firm, Olivia Pope is the ultimate fixer, brilliant, fearless, and morally complex. Working for her means operating in high-stakes, high-pressure environments where loyalty is everything.
Tony Stark – Iron Man / Marvel Cinematic Universe
As the billionaire genius behind Stark Industries, Tony Stark is bold, brilliant, and completely unpredictable. He thrives on innovation and risk, often pushing boundaries with little concern for protocol. Working for him would mean access to cutting-edge tech and the constant possibility of disaster.
Miranda Priestly – The Devil Wears Prada
Intimidating, icy, and impossibly chic, Miranda Priestly (played by Meryl Streep) runs the fashion magazine Runway with an iron will and razor-sharp instincts. We all felt the fear Anne Hathaway’s character did when Miranda Priestly fixed her with that icy stare. While working for her would be a daily exercise in survival, her exacting standards and influence in the industry are unmatched. Beneath the frosty demeanor is a woman who’s made sacrifices for success.
Jack Donaghy – 30 Rock
As an NBC executive with a passion for capitalism and an encyclopedic knowledge of business theory, Jack Donaghy is sharp, strategic, and occasionally ruthless. Yet, the character portrayed by Alec Baldwin he forms an unexpectedly supportive mentorship with Liz Lemon, proving there’s a heart under the expensive suits.
Jules Ostin – The Intern
Robert De Niro and Anne Hathaway formed an unexpected yet iconic duo in The Intern, where De Niro plays the intern and Hathaway the boss. Jules Ostin, the driven founder of an online fashion startup, is a modern leader navigating rapid growth and personal sacrifice. She’s sharp, compassionate, and deeply invested in her company—though often stretched thin trying to balance it all. While initially reluctant about the company’s new senior internship program, Jules gradually learns valuable lessons from her experienced intern.
Gordon Ramsay – Hell’s Kitchen
The real Gordon Ramsay is terrifying on TV, and his fictionalized self in Hell’s Kitchen doesn’t hold back either. He is known for explosive outbursts and impossibly high standards, but he’ll also push you to your limits and beyond.
Margaret Tate – The Proposal
As a high-powered editor at a New York publishing house, Margaret Tate is feared by her employees for good reason: she’s cold, demanding, and unapologetically strict. But beneath the icy facade is someone who’s just as vulnerable as the rest of us.