Top Five… Movie Bosses You Would Like To Work For

To mark the release of new comedy Horrible Bosses with a twist, Ross McG has decided to pick out the cinematic head honchos who didn’t set out to ruin their workers’ lives. These are the movie bosses you’d be happy to go for a drink with after work.

5. Doug Coughlin (Bryan Brown) – the boss from Cocktail

Cruise and Brown's screen test for Twins was something of a disaster

If you are of a certain age (born in the late 70s to early 80s), Cocktail was at one point the coolest film you had ever seen. In its own messed-up, poetry-quoting, white trouser-wearing way, it was the 80s’ answer to Pulp Fiction – considered hip by everyone under the age of 16. If a viewing on a VCR of Cocktail coincided with your puberty, there was no resisting it. Cocktail had everything: regular access to a bar years before you were allowed to enter a real one (I can only speak for myself when I say I was incredibly disappointed a few years later to find barmen didn’t spend 20 minutes dancing to Addicted To Love while you were waiting on your drink); Elisabeth Shue naked under a waterfall (Daniel Laruso never got that far with her) and its most important ingredient… Bryan flipping Brown. As Doug Coughlin, the bar manager who gives cocky Tom Cruise his big break in the twirling-drink-shakers-to-crap-music business, Brown oozes cool. When you’re a teenager, this is the boss you dream of having (if you even dreamt of having a job as a teenager). He can teach you how to pour drinks. He can teach you how to look cool while pouring drinks. He can teach you how to get chicks. He even has his own set of laws! Okay, so his laws make sense if you want to end up 1. an alcoholic and 2. a dead alcoholic, and he’s just as likely to sleep with your new girlfriend as help you find her in the first place, but his heart’s in the right place. And as most movie bosses are heartless bastards, he sneaks on to this list.

4. Daniel Clamp (John Glover) – the boss from Gremlins 2: The New Batch

The Muppets Christmas Special was really messed up

John Glover has a bit of a talent for playing bosses. These days he’s best known for bossing Superman’s nemesis around as Lex Luthor’s dad (seriously, does anyone actually watch Smallville? I’m genuinely interested to know…) but for us he will be most fondly remembered for two particular higher-ups. He slimed his way through 1988 Christmas gem Scrooged as the brilliantly named Brice Cummings, although he had to portray something of an asshole to make Bill Murray’s executive asshole look somewhat less of an asshole. It’s complicated. Two years later, in underrated sequel Gremlins 2, while he once again plays a bit of a self-involved jerk, it’s a self-involved jerk who is really quite loveable. Donald Trump CEO-alike Daniel Clamp may be the owner of a major corporation, but that doesn’t stop him getting his hands dirty when his corporation is overrun by little green monsters. And behind that false-looking toothy grin, he’s not averse to mixing with the little guy, even giving Gizmo-sitter Billy Peltzer a promotion just because he drew a picture of his home town. The coolest thing about Clamp, however, is his secret passageway telephone booth that takes him in and out of his building. In your face, Superman.

3. Cleo McDowell (John Amos) – the boss from Coming To America

'No Juno... YOU hang up..'

Forget that he is only interested in money. Forget that his fast food outlet, McDowell’s, is a lame copy of a rather well-known restaurant chain. Cleo McDowell is a good boss. He is an equal opportunities employer, whether you are an African prince or an African prince pretending to have no money in Queens, New York City. And after a few days mopping floors, disarming Samuel L Jackson and catching milkshakes thrown at you by a man with a shiny permed head, Mr McDowell will invite you to his home, albeit to work some more for him helping out at his parties. But if you’re stuck for a job, have no qualifications and have just come in off the boat… the man who invented the Big Mick burger (like the Big Mac, only no sesame seeds in the bun) will give you a chance. It’s enough to make your Soul Glo.

2. Tony’s Boss (Alan Arkin) – the boss from So I Married An Axe Murderer

It had been a rough couple of years in the stock market for Gordon Gekko

Dirty Harry. Martin Riggs. John McClane. All the best movie cops are chewed out at some stage by a volatile chief, who tells them they’re off the case if they don’t stop playing by their own rules and that the DA is on their back to get results. So it’s a pleasant surprise in Mike Myers’ quirky follow-up to Wayne’s World when Alan Arkin, the head of police overseeing the progress of officer Tony Giardino (Anthony LaPaglia) is the nicest guy – nevermind boss – you’re ever likely to meet. When Tony gets fed up of the his superior’s soft approach (‘Somebody needs a hug!), he asks him to bawl him out a little more. The chief’s subsequent attempts at aggression just make him all the more sweet. I’d bring this cop a case of doughnuts any day.

1. Mr MacMillan (Robert Loggia) – the boss from Big

Andre the Giant was going to be really pissed when he found footprints all over his piano

Most movie bosses (I’m looking at you, Bill Lumberg) just want their drones to stare at a grey wall in an office cubicle all day, but our top movie boss lets you spread your wings, find your inner child and will even dance with you on a giant electronic piano. Step forward Mr MacMillan, so great he doesn’t even need a first name. This guy offers us all hope that our dream job could be just one chance encounter with a friendly old man in a toy shop away. Despite his blatant flouting of child labour laws – his latest employee is after all only 13, even if he is trapped in the body of a grown man – Mr MacM has a good eye for talent and even if you run out of a board meeting he’s hosting and never return again, he won’t hold it against you.


Follow Ross v Ross at


24 Responses to “Top Five… Movie Bosses You Would Like To Work For”

  1. Albert Finney as Edward Massey in “Erin Brockovich” has to be one of the greatest bosses ever. Also would have loved to work at the electronics store with Jane Lynch in “40 Year Old Virgin”

  2. good shout Markuswelby1 – Jane Lynch always gives good boss.

  3. nowhereman136 Says:

    Willy Wonka, President from “ID4”, Im stretching alittle by saying God from Bruce/Evan Almighty and any coach from a sports movie. But thats what comes to mind

    and im amazed you missed Oskar Schindler from “Schindlers List”

  4. Hmmm not so sure about working for Sue Sylvester, Marcus. Maybe one of my friends working for her so we could go in and laugh at him for a bit, but then go back to our normal jobs

  5. Yeah Oskar seems like a nice guy, although working for him meant you were a Jew working around the corner from a concentration camp, not great for morale

  6. good shout on Schindler nowhereman136.. cant think of too many bosses who would save their workers’ lives

  7. Alan Arkin as Arnie Klein in Marley & Me. Helps John Grogan write better. A switch to better life from being a reporter to a columnist and giving the subtle hints to tackling life as he grows.

  8. Apathygrrl Says:

    Joe from Empire Records. Really cool guy. He really cares about his employees and does everything he can to help them out. He even hires the guy who got caught shoplifting from the store. Plus he’ll party with the employees on the rooftop at the end of the day.

  9. Hey Rosses, congrats on making the IMDb hitlist. Way to go fellas!!

    I love the fact you put Clamp on here. The perpeutal 12 year old but billionaire entrepreneur; what a great but mainly aloof character:)

    Call me crazy but I wouldn’t mind working for construction contractor Doug Kinney (Michael Keaton) in Multiplicity…I think a day on the job site would be ok as long as I didn’t show up late:P

  10. Oh and maybe Big Weld from “Robots”. Cme on, it’s lovable Mel Brooks’ CG counterpart…everyone needs a boss like that right?:)

  11. Armstrong Says:

    Tom’s boss in 500 Days of Summer played by Clark Gregg. Very understanding, thoughtful and caring guy.
    Perhaps not the epitome of cool, but solid individual.

  12. […] The Cinematic Bosses We Would All Like To Work For from […]

  13. Havent seen Robots yet, recorded it on DVR ages ago. Worth watching?

  14. It’s cute, better than most non Pixar CG flicks and has surprising amounts of wit, charm and laughs…if you’ve got it on DVR (read: free) you pretty much can’t lose. BTW it looks gorgeous on BD.

  15. Apathygirl.. great shout on Empire Records! Anthony LaPaglia returning the good favour from his boss in So I Married… to being a good one himself. like it when he kicks the guy out of Grease 2 out of the store for being a sleaze

  16. Marc.. who wouldnt wanna work for four Michael Keatons?

  17. neoanakinpotter Says:

    I would have to say Becky Scott (Rosario Dawson) from Clerks 2. Not only do you get to stay late working on the “prep table” sometimes…but she’ll take you dancing on the roof & let you just kick it in the boss’ office painting her toenails leaving your best friend to deal w/ all the hobbit loving customers! lol

  18. Great list! I was going to say Tony’s boss from So I Married an Axe Murderer, but then you beat me to it. Well played, Ross vs. Ross. Well played.

  19. Joanna Cassidy from Don’t Tell Mom the Babysitter’s Dead would be a good one. If you don’t have the experience, fake it using a resume from a book. If you are broke, here’s something called petty cash. And when you finally get busted by your mother, it’s OK, she will still offer you a full time position. Overall, a bit clueless, but a cool boss to have.

    Neo, good choice with Becky Scott. Wish I had a boss like she was when I worked fast food.

  20. Just gotta say, Jennifer Aniston in Horrible Bosses. She didn’t seem like such a bad boss to me. Looked like a rather enjoyable workplace.

  21. Casper Friendly Says:

    I gotta go with Mr. Cheezle (Kevin Nealon) from Grandma’s Boy… –

  22. […] Top 5 Movies You want to work for (Ross vs Ross) […]

  23. Belated congrats on the hit list, guys… looks like we both lucked out last week w/ IMDb 😀

    As for movie bosses I like to work for… hmmm, you got me, I don’t know, but I love my REAL boss so I guess I’m quite blessed in that regard.

  24. Great top 5 guys. Speaking on Bryan Brown I wouldn’t mind working for him in F/X. It would be cool making all those special-effects gizmos for the movies…could do without all the actual murdering mind you.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: