Bad bosses in media

Michael Scott, played by Steve Carell in The Office

Bill Lumbergh, played by Gary Cole in Office Space

The pointy haired boss in Dilbert by Scott Adams

Colin Farrell, Jennifer Aniston, and Kevin Spacey in Horrible Bosses

Louie De Palma, played by Danny DeVito in Taxi

Mr. Burns, voiced by Harry Shearer in The Simpsons

Buddy Ackerman, played by Kevin Spacey in Swimming with Sharks