14 On-Screen Bosses Who Make Us Cringe

Sometimes, you get stuck with a bad boss. Someone who makes you work weekends…or who, like, clips their nails at their desk. Maybe you’ve thought about quitting, but you’ve probably (we hope) never gone to extremes like the guys from Horrible Bosses 2.  In honor of them – and anyone who’s ever dealt with a bad boss – here are some of the most cringeworthy bosses in movies and television.

1. Miranda Priestly (Meryl Streep) in The Devil Wears Prada


Miranda Priestly is probably the scariest kind of boss because she’s so calm about it all, even when she’s saying something completely soul-crushing.

2. Bobby Pellitt (Colin Farrell) in Horrible Bosses


Ok so there are several awful bosses in this movie, hence the title, but we’re singling out Bobby because he represents nepotism, incompetence and really bad combovers. He’s also a raging cocaine addict. Bad, bad, bad.

3. Bill Lumbergh (Gary Cole) in Office Space


Lumbergh is the epitome of the annoying boss. He makes his employees work weekends, he’s a stickler for pointless TPS reports, and he says things like “I’m gonna need you to…” right before assigning you a mundane task.

4. Michael Scott (Steve Carell) in The Office



We love Michael Scott, but man did he make us cringe. Whether he was telling an inappropriate joke or running down one of his employees with his car, he was simply not meant to be a boss.

5. David Brent (Ricky Gervais) in The Office (UK)


David Brent had even less of a clue than Michael Scott, if that’s possible. He thinks his workers look up to him as a mentor, but they really don’t respect him at all.

6. Miranda Bailey (Chandra Wilson) in Grey’s Anatomy


We’ve seen Bailey’s softer side, but remember when she was known only as “The Nazi”? She kept those interns in line!

7. Margaret Tate (Sandra Bullock) in The Proposal


This Canadian boss lady forces her assistant to pretend he’s her fiancé in order to avoid deportation. Not only is that totally awkward, it’s an HR nightmare! Thankfully Ryan Reynolds was very accommodating.

8. Don Draper (Jon Hamm) in Mad Men


Granted Don Draper is good at what he does, but he’s kind of the worst boss. Just ask Peggy – she’s seen his bad side on more than one occasion. He sleeps with his secretaries, drinks during the day and takes frequent naps on the couch in his office.

9. President Snow (Donald Sutherland) in The Hunger Games


He’s the boss of an entire country and he’s completely evil. Definitely not a person you want in charge. He sends children to fight to the death basically for his own amusement.

10. Walter White (Bryan Cranston) in Breaking Bad



He wasn’t so much a boss as he was a, well, kingpin, but he still had complete control over his “employee” Jesse Pinkman. All that manipulation really made us cringe!

11. Maria Laguerta (Lauren Velez) in Dexter


Over the course of Dexter, the fiercely ambitious Laguerta went from Lieutenant to Captain of the Miami Metro Police Department and never failed to make Debra Morgan’s life a living hell.

12. Carter Duryea (Topher Grace) in In Good Company


At 26, he became the boss at an established sports magazine and was forced to manage people with way more experience than him – namely Dennis Quaid’s Dan Foreman. He was all about promoting “synergy,” despite having little to no clue what that actually meant. 

13. Ron Swanson (Nick Offerman) in Parks and Recreation



Don’t get us wrong, we love everything about Ron Swanson – from his mustache to his deep and abiding love of red meat. But he works in city government and actively tries to make it less effective. Not exactly someone you want running things.

14. Jordan Belfort (Leonardo DiCaprio) in The Wolf of Wall Street


Belfort represented Wall Street corruption at its worst. He ran his firm with no ethical standards, and when he was caught, he barely got any jail time! Most cringeworthy thing about this guy is that he actually existed!

Which on-screen boss makes YOU cringe? Let us know on Twitter!