By Dustin Rowles | Posted Under Seriously Random Lists | Comments (58)
5. Bill Lumbergh (Gary Cole) in Office Space
4. Mr. Grey (James Spader) in Secretary
3. Miranda Priestley (Meryl Streep) in The Devil Wears Prada
2. Blake (Alec Baldwin) in Glengarry Glen Ross
1. Buddy Ackerman (Kevin Spacey) in Swimming with Sharks
← American Idol Can Suck My Nuts | DVD Releases →
Posted by: BarbadoSlim at April 28, 2009 4:07 PM
In a creepy twist of reality.
5. I used to work for someone EXACTLY like Bill Lumbergh
3. My mother looks EXACTLY like Miranda Priestley (and my mom was president of a clothing department store).
3a. I happen to look exactly like Anna Wintour, the real editor of Vogue, who was the basis for the character of Miranda Priestley. Like mother, like daughter. Scary.
Posted by: BWeaves at April 28, 2009 4:12 PM
How about Dabney Coleman in 9 to 5? Hello?
And I personally would not be averse to Mr. Grey's method of dealing with typos. But that's just me.
Posted by: MG at April 28, 2009 4:13 PM
"God no, she's not with Lumbergh. The baby would come out with hooves."
Bless you for not mentioning the two-dimensional fat joke from Wanted.
Posted by: twig at April 28, 2009 4:16 PM
Mr. Grey (James Spader) in Secretary
Speak for yourself Dustin. James Spader in Secretary was the best boss ever. James Spader in Secretary is my dream boss. James Spader in Secretary..oh, I have to stop myself now before I spontaneously orgasm.
Posted by: Cindy at April 28, 2009 4:16 PM
Hey, how about that character played by Kevin Spacey in that movie with the kid from Career Opportunities? The one were the assistant has a meltdown turns the tables and tortures him and shit.
Posted by: BarbadoSlim at April 28, 2009 4:17 PM
Maggie G. was positively brilliant in that role.
Posted by: samantha t at April 28, 2009 4:19 PM
Streep was, seriously, the only interesting thing about "Devil." Oh, and the movie completely revealed how much of a man Gisele Bundchen is when put next to the stunning Emily Blunt.
Posted by: samantha t at April 28, 2009 4:22 PM
Alec Baldwin wasn't the boss in Glengarry, Kevin Spacey was (and he was a sucky boss in that one too), but that is one motivating speech. I think it's my favorite scene in a movie full of awesome scenes.
Posted by: Chickaboom at April 28, 2009 4:27 PM
Darth Vader would indeed be a terrible boss. But I'd take him over Governor Tarkin.
If you were late with your TPS reports, Vader would choke a bitch or just kill you with a lightsaber. Tarkin would have you scrubbing the insides of all the toilets on the Destroyer WHILE BEING FLAYED ALIVE.
Posted by: malechai at April 28, 2009 4:38 PM
Chris Cooper in Breach was pretty rough.
Posted by: TK at April 28, 2009 4:39 PM
Gordon Gekko.
Posted by: Recondite at April 28, 2009 4:41 PM
Oy, drugs are bad kids, disregard my Kevin Spacey coment.
Posted by: BarbadoSlim at April 28, 2009 4:42 PM
How about...Sigourney Weaver in Working Girl, the original powercunt.
Posted by: BarbadoSlim at April 28, 2009 4:47 PM
"I'll have the penne al'aribiata."
Posted by: lizzieborden at April 28, 2009 4:47 PM
You'll need a tray.
Posted by: twig at April 28, 2009 4:56 PM
Michael Scott.
Not from movies, but he's the worst boss of all time.
Posted by: figgy at April 28, 2009 4:58 PM
This one is wet.
Posted by: Graham at April 28, 2009 5:07 PM
I concur Figgy. Worst boss ever.
Posted by: Heathen at April 28, 2009 5:09 PM
Woah, woah, Mr. Grey is not the worst boss of all time. Uh, I mean, you know, if you're into that kind of thing.
Michael Scott is not the worst boss of all time, at least his idiocy comes from an honest place. David Brent was a much more loathable boss. True story, the boss I had at my own campus job was like a mix of Michael Scott and Bill Lumbergh (mostly Lumbergh), in a lady's body. *grits teeth* There is no sarcastic quip to make here. She was just the worst.
Posted by: Kayanne at April 28, 2009 5:13 PM
Captain Vidal, Pan's Labyrinth
Dude will mess you up. Work is ACTUAL torture.
Posted by: kx2 at April 28, 2009 5:18 PM
Ralph Fiennes' concentration camp overlord in "Schindler's List". Every boss ever looks awesome next to his leadership style.
Posted by: Kballs at April 28, 2009 5:21 PM
When I read the book, The Devil Wears Prada, I took home completely the wrong message. Basically it wasn't so much that Miranda Priestly was an awful boss (she was only moderately awful), but that she got wet behind the ears girls to work for her. They spent all their time being terrified of her, when they could have been managing her. And the the main character said it herself, if the two secretaries assistants had worked together the job would have been 10 times easier. e.g. if one had a birthday party, the other could have arranged to be on call, rather than being incommunicado and making her colleage work through her own birthday party.
Posted by: ChrisD at April 28, 2009 5:25 PM
Mr. Grey can count my peas anytime.
Posted by: Stacy D at April 28, 2009 5:29 PM
I'll second Dabney Coleman in "9 to 5" (which totally dates me, eh?)
Posted by: Kristi at April 28, 2009 5:53 PM
BSlim - Swimming with Sharks
I third the call for Dabney Coleman (Frank Hart) in "9 to 5". He's the first one I thought of when I read this headline, after Lundberg.
Posted by: TylerDFC at April 28, 2009 5:56 PM
Perhaps this is revealing too much, but I'd love to be Mr. Grey to someone's Lee.
Actually sexual harassment suits notwithstanding, of course.
That movie ruled.
~ ~ ~ ~ ~
On another note, I think Alec Baldwin's brief performance in GGR stood out so much because it revealed, for the first and last time, that he could actually fucking act. Who knew?
Posted by: Big Daddy Bacchus at April 28, 2009 6:15 PM
Yeah, Dabney should be on this list.
I had a boss who sounded just like Lumbergh, but was the nicest guy. Heavy into micromanaging, but nice.
What was wrong with Mr. Grey's tactics? Wouldn't that be a plus in the corporate world? Unless you bruise easily.
Posted by: Brie at April 28, 2009 6:19 PM
Dick Cheney in the Bush Administration ... that was one long ass movie
oh wait ... I see he's already been mentioned on this thread ....
Posted by: lelnguye at April 28, 2009 6:21 PM
This one is wet, this one is wet, this one is wet--did you dry these in a fucking rainforest?
Posted by: grace b at April 28, 2009 6:22 PM
That boss from The Apartment was no bargain.
Posted by: Steve at April 28, 2009 6:32 PM
Buddy Ackerman absolutely deserves #1.
Ugh, I've worked for people like him. It's barely a parody.
Posted by: TL at April 28, 2009 6:53 PM
You'll need a tray.
Come on, twig! Vader isn't the boss. Mr. Stephens is the boss!
Posted by: Opie Curious at April 28, 2009 6:53 PM
The head of catering?
Posted by: twig at April 28, 2009 6:54 PM
Denzel in Training Day was kind of a douche.
Posted by: David M at April 28, 2009 7:15 PM
Dan Halen from Squidbillies, ultimate evil boss.
Posted by: BarbadoSlim at April 28, 2009 7:18 PM
If you've ever been a nanny for the uber-rich on the Upper East Side of Manhattan, you've had a boss like Miranda Priestley in The Devil Wears Prada. I made great money and saw the world for three years but came out scarred, tear-stained and hating children. The Nanny Diaries is 100% true!!!!
Posted by: scorzi at April 28, 2009 8:03 PM
James Spader in Secretary was the last time I wanted to fuck James Spader. (He just got too plump after that.)
I frickin' love that movie.
Posted by: Jerce at April 28, 2009 8:29 PM
Alec Baldwin was not the boss in Glengary Glen Ross, he was doing a favor for Mitch and Murray.
Posted by: LwoodPDowd at April 28, 2009 9:02 PM
Todd Barry as Wayne in The Wrestler is cartoonishly unlikable.
Also, outside movies, William Rawls from The Wire is a fucking reprobate.
Posted by: Benny at April 28, 2009 9:37 PM
that creepy ass dude that audrey tautou's character worked for in dirty pretty things.
Posted by: stopthemadness at April 28, 2009 10:14 PM
I heard that there is an inter esting place for all h O t g irls and guys,
seems it is named: ___Tallmingle Co M___ ,if u want to find some fun or lov ers, please have a try !!!
Posted by: Jack at April 28, 2009 10:21 PM
here here, BarbadoSlim! When I saw this title, Sigourney Weaver in Working Girl was the first boss who came to mind. Genuinely horrifying (and insanely funny)...can guarantee that Meryl Streep watched her to pick up tips for Prada.
Posted by: jules at April 28, 2009 10:28 PM
the asshole who wanted to reach new york in record time, thus dooming the titanic.
he sort of sucked.
Posted by: stopthemadness at April 28, 2009 10:33 PM
Good call on Swimming With Sharks. I actually assumed you were going to pass it over in light of Spacey's general uncoolness on this site.
Posted by: Laughner at April 28, 2009 11:04 PM
is no one going to mention meg foster in leviathan?
Posted by: gp at April 28, 2009 11:30 PM
Nurse Ratched in One Flew Over the Cuckoo's Nest.
Posted by: Mattfactor at April 28, 2009 11:33 PM
If you meant to say BEST boss ever, then James Spader in Secretary tops the list. Holy crap, that man is sex walking.
Posted by: Melissa at April 29, 2009 12:23 AM
Graham Chapman, King Arthur, "Monty Python and the Holy Grail."
LOOK at the BONES!
Posted by: , (the commenter formerly known as bucdaddy) at April 29, 2009 12:24 AM
James Spader does not deserve to be on this list, not at all. That man could spank me any time.
I go along with Dabney Coleman. What a prick! I still love to hate him in that movie, and I get happy every time I see him hoisted into the air by a garage door opener.
Posted by: Sharon at April 29, 2009 12:35 AM
Paul Newman in The Hudsucker Proxy. I mean, he sets up a mailroom simpleton to make the company stock plummet after the suicide of his biz partner, just so he can rape the stockholders for millions. It's like Enron, Halliburton, and AIG, only set in the 1930s.
Posted by: ceejeemcbeegee at April 29, 2009 2:12 AM
Kudos, Twig & Lizzieborden, Big Monkeyfighting Kudos!!!
Posted by: missh at April 29, 2009 6:12 AM
"Good Morning" Grant from Reality Bites.
Posted by: Whorish Mouth at April 29, 2009 9:04 AM
Really, tcfkabd, and all because some moist bint tossed him a sword in some farcical aqautic ceremony. Help, help, I'm being oppressed.
Posted by: slower lower at April 29, 2009 9:08 AM
I agree with those who think Spader in Secretary is an example of a GOOD boss.
Posted by: Less Lee Moore at April 29, 2009 11:15 AM
I'd work for either Miranda or Mr. Grey in a heartbeat. And for such different yet oh-so-sexy reasons.
Posted by: Sweetie Dahling at April 29, 2009 11:16 AM
I'd work for Mr. Grey. And I by work I mean I would... well, you know where this is going.
Posted by: superEdna at April 29, 2009 1:13 PM
i have been DREAMING of one day having a boss like MR. GREY.
Posted by: jessie-marie at April 29, 2009 2:36 PM
No Darth Vader?
You are useless Rowles.