The 20 Most Terrible On-Screen Bosses

The 20 Most Terrible On-Screen Bosses

Gordon Ramsay putting two pieces of bread on a chef's ears and saying 'what are you' she replies 'an idiot sandwich'Last week we posted a blog called: The 10 Worst (Real-Life) Bosses – Could You Cope?

Some of the stories we discovered were so peculiar and unbelievable that we just had to ask ourselves… where do these bosses get their management techniques from?

What on earth has possessed them to be so. bloody. irresponsible?

And then, a light-bulb switched on! Could these truly horrible bosses be taking advice from the movie stars? Maybe… (probably not.)

Either way, this week we’ve come up with the 20 most terrible on-screen bosses to grace the silver screen.

Warning: If you’re easily offended by bad language and sexual innuendo, then you might just want to skip this blog…

1. Hilly Holbrook (Bryce Dallas Howard)

Hilly Holbrook from the Help - wretchingFilm: The Help

Charged with: Being a terrible, racist witch (don’t worry, she gets her comeuppance… But you’ll have to watch to find out how).

Terrible boss quote: “They carry different diseases than we do. That’s why I’ve drafted the Home Health Sanitation Initiative.”

2. Gregory House (Hugh Laurie)

House with quote 'wow, you're ugly'TV Programme: House

Charged with: supreme arrogance and an inability to understand other points of view. Dr. House refuses to visit his patients, is willing to put their lives at risk on a whim and is quite happy to put his team’s jobs on the line for his own personal gain. Also, he’s addicted to pain medication… shockingly, he’s the hero of the show!

Terrible boss quote: “It’s nothing personal. I don’t like anybody”

3. Mark Zuckerberg (Jesse Eisenberg)

Mark Zuckerberg looking bored - with quote 'oops'Film: The Social Network

Charged with: Arrogance, paranoia, screwing over his friend and creating Facebook for the sole aim of attracting women – no wonder the real Mark Zuckerberg wasn’t a fan of his portrayal on the big screen.

Terrible boss quote: Eduardo Saverin (his friend): “You set me up.” Mark Zuckerberg: “You’re gonna blame me because you were the business head of the company and you made a bad business deal with your own company?” Ruthless.

4. Dudley Smith (James Cromwell)

Film: L.A. Confidential

Charged with: corruption, bullying, murder, extortion, general conniving. Basically an all-round snake, oh and an LAPD captain! Perfect.

Terrible boss quote: Dudley Smith: “Would you be willing to shoot a hardened criminal in the back, in order to offset the chance that some lawyer…” Ed Exley: “No” Dudley Smith: “Then, for the love of God, don’t be a detective.”

Dudley Smith shooting a man without warning

5. Dr Evil (Mike Myers)

Dr Evil laughing an evil laughFilm: Austin Powers

Charged with: It’s sort of in the name really..? Demanding, stubborn, sarcastic and just a little bit silly. Of course, woe betide you if you get on his wrong side; you could get beaten, shot, run over by a steamroller, thrown into boiling hot lava…or worse.

Terrible boss quote: “That makes me angry. And when Dr. Evil gets angry, Mr. Bigglesworth gets upset. And when Mr. Bigglesworth gets upset, people DIE!!”

6. Les Grossman (Tom Cruise)

les grossman dancing Film: Tropic Thunder

Charged with: Les, as his name would suggest is genuinely quite a ‘gross man.’ Sporting an outrageous ‘do, swearing constantly and showing off some absolutely killer dance moves, it’s impossible to take him seriously.

Terrible boss quote: “Look f#ck stick, I’m incredibly busy. So why don’t you get the hell out of here before I snap your d#ck off and jam it into your…” (In my defence, it was pretty difficult to find a quote without numerous swear words and offensive language.

7. Katharine Parker (Sigourney Weaver)

Katherine parker with quote - I'm getting tired of this sh*tFilm: Working Girl

Charged with: conniving and taking credit for her employees’ ideas, Katharine is a truly formidable and back-stabbing boss.Would you mess with the Weaver?

Terrible boss quote: “Why that little… slut! B#tch! Secretary!”

8. Daniel Cleaver (Hugh Grant)

Daniel cleaver fighting mark darcy in the streetsFilm: Bridget Jones’s Diary

Charged with: acting like a chauvinistic pig. Daniel pursues our lovable heroine Bridget by making outrageous comments about her clothing (namely, a non-existent skirt). True, Bridget does give as good as she gets but she also falls for Daniel who goes on to break her heart by sleeping with a younger model.

Terrible boss quote: Via Email: “Mortified to have caused offense. Will avoid all non-P.C. overtones in future. Deeply apologetic. P.S. Like your t#ts in that top.”

9. John Milton (Al Pacino)

Film: The Devil’s Advocate

Charged with: being the devil! Al Pacino’s chilling representation of Satan (a New York law firm rep) who hires poor, unsuspecting Kevin Lomax and subjects him to a terrible set of demonic events certainly doesn’t disappoint.

Terrible boss quote: “The law, my boy, puts us into everything. It’s the ultimate backstage pass; it’s the new priesthood, baby. Did you know there are more students in law school than there are lawyers walking the Earth? We’re coming out, guns blazing! The two of you, all of us, acquittal after acquittal after acquittal… until the stench of it reaches so high and far into heaven, it chokes the whole lot of them.”

John Milton terribly on-screen bosses 

10. Michael Corleone (Al Pacino)

Michael Corleone giving Fredo a kissFilm: The Godfather Part 2

Charged with: killing his own brother. Now here’s a gangster who takes his job very seriously… when Fredo (his slightly dimwitted brother and a member of his entourage) admits he betrayed him – he was promised that Michael wouldn’t be harmed – Michael has him murdered. If Michael could do that to his own brother, just imagine what he’d do to you.

Terrible boss quote: As he gives Fredo a terrifying, emotional Sicilian kiss of death, sealing his fate: “I know it was you Fredo. You broke my heart. You broke my heart!”

11. Darth Vader (David Prowse)

Film: Star Wars IV – A New Hope

Charged with: being on the dark side. From the first time you meet Darth Vader, you just know he’s not someone you should mess with, let alone work for. During the three classic films he randomly ‘force chokes’ his staff for being insolent, annoying or just a bit stupid. (Yes, yes, he turns out to be good in the end… but you still wouldn’t want to work for him)!

Terrible boss quote: To Luke:Give yourself to the Dark Side. It is the only way you can save your friends. Yes, your thoughts betray you. Your feelings for them are strong. Especially for… sister. So, you have a twin sister. Your feelings have now betrayed her, too.”

12. Michael Scott (Steve Carell)

Michael Scott telling Toby (HR) he's going to kill himTV programme: The Office (USA)

Charged with: acting like a clown. Everyone loves Michael Scott, but that doesn’t necessarily mean that you’d want him as your boss! Spending the majority of his time distracting others, getting his staff into trouble and avoiding doing any work for himself – oh and he’s also got an irrational hatred for the HR rep. What a great role model…

Terrible boss quote: “If I had a gun with two bullets and I was in a room with Hitler, Bin Laden and Toby, I would shoot Toby twice”

13. David Brent (Ricky Gervais)

Ricky Gervais doing his danceTV programme: The Office (UK)

Charged with: acting like a clown. Our list of terrible on-screen bosses could never, ever be complete without including Michael Scott’s British counterpart. Cocky, annoying and sometimes genuinely nasty, yet we all love (to hate) him!

Terrible boss quote: “My proudest moment here wasn’t when I increased profits by 17%, or cut expenditure without losing a single member of staff. No. It was a young Greek guy, first job in the country, hardly spoke a word of English, but he came to me and he went “Mr. Brent, will you be the Godfather to my child?”. Didn’t happen in the end. We had to let him go, he was rubbish. He was rubbish!”

14. Bill (David Carradine)

Film: Kill Bill

Charged with: attempted murder. Beatrix Kiddo had had a enough of the assassin’s life. She just wanted to settle down, forget about her co-assassin ex-lover, ex-boss Bill and marry her new (normal) fiancé. But Bill’s having none of it. He rocks up, gang of trained killers in tow and attempts to kill everyone in the church, including his very own unborn child.

Terrible boss quote: Staring out at the dying bride: “Do you find me sadistic? You know, I’ll bet I could fry an egg on your head right now if I wanted to. No, Kiddo, I’d like to believe you’re aware enough, even now, to know there’s nothing sadistic in my actions. Maybe towards those other jokers, but not you. No, Kiddo, this moment, this is me at my most … masochistic.”

Bill saying 'some things, once you do, they can never be undone'

15. Miranda Priestly (Meryl Streep)

Film: The Devil Wears Prada

Charged with: acting like a complete and utter thoughtless queen-b#tch. Miranda Priestly has all of her staff jumping through hoops for her. They’re expected to work around the clock and compete mercilessly with co-workers. One wrong move and you’re out of the door; she didn’t get to where she is by being nice.

Terrible boss quote: Miranda: “You have no style or sense of fashion’ Andrea: “I think that depends on…” Miranda: “No, no, that wasn’t a question.’

Miranda Priestly - did you fall down and smach your little head off the pavement?





16. Montgomery Burns (Harry Shearer)

Mr Burns doing an evil laughTV Programme: The Simpsons

Charged with: an extreme addiction to money. Mr. Burns doesn’t care who he hurts on his quest to becoming rich, including his sidekick (and best pal/ would-be lover) Smithers, who’ll pretty much do anything for his boss. His evil plots have ranged from creating dangerous labs that could wipe out the whole of Springfield to becoming the pope (to gain power)!

Terrible boss quote: “Release the Hounds” (oh and I simply couldn’t leave out “Excellent”).

17. E. Edward Grey (James Spader)

secretary bent over deskFilm: Secretary

Charged with: sexual harassment at it’s worst. Lee Holloway starts working as a secretary for E. Edward Grey after a short stint in a mental health institution. Their professional relationship soon turns sadomasochistic and Lee is coerced into some very compromising positions. Christian eat your heart out… this is the original Mr. Grey.

Terrible boss quote:  Telling Lee what she will eat for dinnerOne scoop of creamed potatoes. A slice of butter. Four peas. And as much ice cream as you’d like to eat.”

18. Brick Top Polford (Alan Ford)

Brick Top PolfordFilm: Snatch

Charged with: murdering his unlucky ‘staff members’ and then feeding their body parts to the pigs. Enough said really.

Terrible boss quote: “You’re always gonna have problems lifting a body in one piece. Apparently the best thing to do is cut up a corpse into six pieces and pile it all together.”

19. Gordon Gekko (Michael Douglas)

Gordon gekko with quote 'The point, ladies and gentlemen, is that greed, for lack of a better word, is good'Film: Wall Street

Charged with: being one ruthless (and fraudulent) investor with the motto: ‘greed is good.’ Stand in Gordon’s way and you’re really going to face the music. Ally yourself with him and you could end up in prison… it’s a lose-lose situation!

Terrible boss quote: “When I get a hold of the son of a b#tch who leaked this, I’m gonna tear his eyeballs out and I’m gonna suck his f#ing skull.”

20. Bill Lumbergh (Gary Cole)

Bill looking shifty and saying 'We have sort of a problem'Film: Office Space

Charged with: crushing the souls of his poor employees with long hours and micromanagement. Probably sounds like the pussycat compared to our other 19 terrible on-screen bosses – right? What’s scary about Bill is that you actually could very easily end up with a boss like him (unlike working for Satan, Darth Vader or a mobster – hopefully).

Terrible boss quote: “Ummm, I’m gonna need you to go ahead come in tomorrow. So if you could be here around 9 that would be great, mmmk… oh oh! and I almost forgot ahh, I’m also gonna need you to go ahead and come in on Sunday too, kay. We ahh lost some people this week and ah, we sorta need to play catch up.”


There you have it – 20 of the most irritating, annoying and downright offensive bosses from the silver screen – could you work for them?

OK – so it’s incredibly unlikely that you’re going the end up working for an overlord of the dark side or a pig-yielding gangster – but that doesn’t mean your bully boss is any less of a plague on your life.

If you find yourself suffering at the hands of an employer, don’t just ride it out and hate your job – do something about it or quit your job!

You don’t want to end up hating your job – it’s not worth it.

Recruiter Pro Tip

If you think YOU are the bully boss… then I urge you to stop, now.

To make your business a real success, you want to attractive creative, engaged people and then retain them – you’re never going to do that with scare tactics.

Bullying costs businesses an estimated £2bn a year in sick pay, staff turnover and productivity… it’s worth remember that figure.

On another topic altogether – fair play to these fantastic actors for making us hate them!

Happy Friday!

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