Top 10 Outrageous TV Bosses

VOICE OVER: Rebecca Brayton
Script written by Nathan Sharp

There are some hilarious and outrageous TV bosses on this list from classic workplace sitcoms. Some are funny, some make you laugh because otherwise you'd have to cry! Featuring the likes of Bob Kelso from Scrubs, Ray Holt from Brooklyn Nine-Nine, Lou Grant from the The Mary Tyler Moore Show, Jimmy James from NewsRadio, Ron Swanson from Parks and Recreation, David Brent & Michael Scott from The Office, Mr. Burns from The Simpsons.

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Script written by Nathan Sharp

Top 10 TV Bosses

You wouldn’t want to work for them in a million years, but you’d watch them on TV any day. Welcome to, and today we’re counting down our picks for the top 10 TV bosses.  

For this list, we’re taking a look at television’s funniest and most relatable employers that bring something unique to the familiar sitcom archetype. Keep in mind that we’re restricting this list to traditional bosses only, so we’re excluding people like Louie De Palma from “Taxi” and Sam Malone from “Cheers.” 

#10: Jimmy James
“NewsRadio” (1995-99)

As owner of Jimmy James Incorporated, Mr. James should command any room he walks into. Instead, the billionaire spends all his free time at the crown jewel of his empire – WNYX. Whether running for president, replacing drive time with old timey radio shows, adding a romance arc to the news, or just enjoying a cracker or two, Mr. James can’t help but inject life, odd ball wisdom, and genuine heart into his chosen playground. As much a father figure to his staff as he is a leader, it’s hard not to love the quirky Jimmy James – the man so nice, they named him twice.  

#9: B.P. Richfield
“Dinosaurs” (1991-94)

It may’ve been set in 60,000,003 (60 million and three) BC and it may’ve been populated with reptiles, but “Dinosaurs” included all the staples found in most American sitcoms: The dysfunctional family, the best friends, and, of course, the intimidating boss. Although B.P. Richfield is a Triceratops and tree pusher Earl Sinclair is a meat-eating Megalosaurus, you often expect this suspender-wearing, hunched over herbivore to devour his subordinate. Wonderfully designed by the puppeteers at Jim Henson Productions and aggressively voiced by Sherman Hemsley, Richfield will do anything to drive up sales at the WESAYSO Development Corporation, ultimately helping to cause his species’ extinction.

#8: Dr. Bob Kelso
“Scrubs” (2001-10)

At first glance, Bob Kelso might come off as a heartless, dishonest, manipulative bureaucrat who only cares about saving his hospital money. While he’s far from the perfect physician or person, there’s more to the Sacred Heart Chief of Medicine than you initially think. Behind his constant insults and acts of adultery, Kelso secretly harbors affection for his co-workers, family, and patients. He’ll just mask such compassion at any cost. After retiring, however, Kelso slowly lets his defenses down and reveals himself as a human being to his peers.

#7: Lou Grant
“The Mary Tyler Moore Show” (1970-77)

News director at WJM-TV and begrudging mentor to Mary Richards, Mr. Grant is a no-nonsense kinda boss. Rough around the edges and a workaholic through-and-through, Lou doesn’t trust many people. But he and Mary have a different kind of working relationship; at times, it’s more like a father-daughter bond than a boss-employee one. He treats all of his workers with respect – well, with the possible exception of the moronic Ted Baxter – and is passionate about the news. But it’s that underlying vulnerability that makes him so fascinating. It’s that complexity that helped Lou Grant become the only TV character to have a lead role in both a successful comedy and drama series.

#6: Capt. Ray Holt
“Brooklyn Nine-Nine” (2013-) 

When you have a work environment as zany as the 99th Precinct, you need a zero-nonsense police captain to balance things out. Played to perfection by a stone-faced Andre Braugher, you can never tell when Captain Holt is happy, angry, or attempting to tell a joke. As a result, almost everything that comes out of his mouth ends up being unintentionally hysterical. While he might not emote much, Holt has overcome many hurtles in life as a gay, African-American to become his department’s respected boss and father figure.

#5: Ron Swanson
“Parks and Recreation” (2009-15)

In most sitcoms, it’s usually the proactive boss who torments his lazy workers. In “Parks and Recreation,” it’s the other way around. Ron Swanson loathes his job as parks department director as well as the government he works for. The polar opposite of City Manager Chris Traeger, Ron will do everything in his power to avoid accomplishing any work, instead dedicating his time to eating breakfast, woodworking, and silently sitting alone in his office. Regardless, he’s constantly forced by his go-getting underling Leslie Knope to help make the world a better place. 

#4: J. Peterman
“Seinfeld” (1989-98)

Although Jerry’s a standup comedian and Kramer’s self-employed – although we use that term loosely – “Seinfeld” still managed to produce some exceptional workplace humor through George and Elaine’s various bosses. As uproarious as Mr. Steinbrenner is, J. Peterman leaves an even greater impression. He’s not the easiest person to work for given his oblivious and unpredictable nature. Peterman is so positively lively, though, that you can’t help but be charmed by him. With a one-of-a-kind voice and infectious personality, John O’Hurley actually created a J. Peterman even more iconic than the real J. Peterman.

#3: Jack Donaghy
“30 Rock” (2006-13)

He might be the most diehard liberal in real life, but Alec Baldwin was born to play ultraconservative businessman and Ronald Reagan devotee Jack Donaghy. Beginning as GE Vice President of East Coast Television and Microwave Oven Programming, Jack uses all his power to influence elections, crush his enemies, and work his way even higher up the ladder. Although Jack views everybody as a giant dollar sign, he always has time to impart wisdom to his mentee Liz Lemon. In exchange, Liz acts as a loyal confidante who somehow manages to bring out Jack’s tender side.

#2: C. Montgomery Burns
“The Simpsons” (1989-)

The richest man in Springfield, USA, Mr. Burns runs his nuclear power plant like a Bond villain – minus the cat-stroking. While his 104-year-old body is on the brink of becoming a corpse, the cogs in his diabolical brain never stop rotating. With his dedicated assistant Waylon Smithers by his side, Burns is frequently cooking up new schemes to benefit himself, like blocking out the sun, depriving his workers of their dental plan, and stealing teddy bears from small children. All of Springfield fears Mr. Burns and would never take a stand against him…unless they happen to be a baby armed with a gun...
Before we get to our top pick, here are a few honorable mentions:
- Avery Bullock 
“American Dad!” (2005-) 
- Malory Archer 
“Archer” (2009-) 
- Mayor Randall Winston 
“Spin City” (1996-2002) 
- Don Draper
“Mad Men” (2007-15)

#1: David Brent & Michael Scott
“The Office” (2001-03; 2005-13)

It seemed appropriate that we group these two “Office” bosses together since they’re so similar, yet so different. David is arguably even more conceited and insensitive whereas Michael is more obnoxious and idiotic – though both are oblivious. When you’re not laughing at them, there’s a good chance you want to slap them across the face. Neither knows when to shut up, which only makes them harder to like. Nevertheless, you can’t help but sympathize with two guys who are so socially inept that they must force relationships on their employees to achieve some form of friendship and family. Actually, that’s pretty harsh: David and Michael are harmless, and pretty lovable in their own special ways.

Do you agree with our list? Who’s your favorite TV boss? For more entertaining Top 10s published every day, be sure to subscribe to