10 TV Bosses You Hope You’ll Never Have

The ten toughest bosses on television.


Normally, TV bosses turn out to be teddy bears when relieved of their tough exterior. But as TV gets darker — and more realistic — there’s a place for the bosses who just won’t compromise. We might admire them, but we would never want to be under them. Here are ten that always get the job done.

10. Charles Montgomery Burns – ‘The Simpsons’

Boss 1

He runs Springfield’s Nuclear Power Plant like a slave labor camp (even if you’re a duck), and has no qualms firing employees (mainly Homer) at will. His evil knows no limits — he even tried to kill the Sun. But never has such a tough mind had such a floppy body.

9. Jack Donaghy – ’30 Rock’


It’s never a good sign if your boss models himself on Ronald Reagan… or at least it doesn’t bode well for your health care plan. Jack has his reasonable side, but would rather manipulatively pressure his workers into doing his bidding. And he fired Kenneth…which you had to be evil to do.

8. Peggy Olson – ‘Mad Men’

Boss 2

Thought Don Draper was tough? At least you could play hooky when he slept one off in his office. His protégé Peggy was far worse. Overbearing, demanding and unforgiving, she’ll settle for nothing less than her own idea repeated back to her by a bunch of lackeys. And Don’s termination.

7. Thomas Bale – ‘NYPD Blue’


Rogue detective Sipowicz could seemingly wrap the hardest of the 15th Precinct’s Lieutenants around his little finger — even the one he racially abused on consecutive occasions. But Bale would have none of his tomfooleries. So ruthless he brought lovable Leprechaun Medavoy up on charges, he had to be shot to finally mellow out.

6. Dr. Hubert J. Farnsworth – ‘Futurama’

Boss 3

He might hide behind the façade of an absent-minded professor but, when it comes to the treatment of his employees, the Planet Express CEO has a record worse than Amazon. Thanks to Farnsworth’s less-than-exacting attitude towards worker safety, he’s got some turnover, and only Leela to keep the numbers respectable.

5. Buck Strickland – ‘King Of The Hill’


You know when you’re initially excited to have a laid-back, fun-loving boss, but then find out that means you have to do all the work? Yep, that’s Buck Strickland. There’s nothing the philandering gambler won’t push on to Assistant Manager Hank’s plate, including an Emu outbreak and a murder charge.

4. Leslie Knope – ‘Parks And Recreation’

Boss 4

Her love for her employees is insurmountable, but so are her expectations of them. Maybe the Assistant Parks Director has to overcompensate because her boss Ron Swanson refuses to intrude on anyone else’s liberty. Or, maybe it’s because everyone in the office does about a third of the work they should.

3. Mr. Justin Pitt – ‘Seinfeld’

Boss 5

The British business mogul terrorized personal assistant Elaine with his indecision over socks, demands for salt to be removed from all his pretzels and magic eye fetish. He nearly deafened her to get a spot under Woody Woodpecker in the Macy’s Thanksgiving Parade. No wonder she tried to kill him.

2. George Bluth – ‘Arrested Development’

Boss 6

The Bluth Company CEO’s people management approach – which relied heavily on amputees – would come over a little strong… even if it wasn’t his family that was on the receiving end. George liked to pit his useless sons against each other in the hopes that he could continue to manage his company from prison.
Tony Soprano – ‘The Sopranos’

As Capo Di Tutti Capi of The New Jersey Mafia, Tony is not above murdering his employees even – no, especially – if they’re family members. He once whipped an Assemblyman on his payroll into impotence. And don’t even think about retiring — he’ll find you even if he has to miss his daughter’s college interview.