Gary Cole in Office Space

Stephanie Prange

October 16, 2020

For National Boss’s Day, Fandango’s transactional streaming service Vudu has programmed a playlist of the most memorably maddening bosses, with a sale on the top movies, led by the 1999 dark comedy Office Space.

“Gary Cole’s soul-crushing, passive-aggressive Lumbergh is everyone’s favorite nightmarish boss,” Fandango editor Erik Davis said in a statement. “And his annoying omnipresence in Mike Judge’s iconic Office Space still haunts us to this day. From Meryl Streep’s hard-charging magazine editor Miranda Priestly to Steve Carell’s clueless branch manager Michael Scott, there is no shortage of awful bosses in movies and TV shows, and fans can head to Vudu to enjoy watching their memorable antics and get much-needed laughs, scare and thrills.”

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The top picks for the worst bosses in movies and TV are:

The Worst Bosses in the Movies:

1. Office Space (Gary Cole)
2. The Devil Wears Prada (Meryl Streep)
3. 9 to 5 (Dabney Colman)
4. Wall Street (Michael Douglas)
5. The Devil’s Advocate (Al Pacino)
6. Horrible Bosses (Jennifer Aniston)
7. Scrooged (Bill Murray)
8. The Wolf of Wall Street (Leonardo DiCaprio)
9. The Social Network (Jesse Eisenberg)
10. Working Girl (Sigourney Weaver)
11. Boiler Room (Ben Affleck)
12. The Proposal (Sandra Bullock)
13. Glengarry Glen Ross (Alec Baldwin)
14. Jurassic World (Bryce Dallas Howard)
15. RoboCop (Ronny Cox)

The Worst Bosses in TV Shows:

1. “The Office” (Steve Carell) and “The Office” (Ricky Gervais) — tied
2. “Mad Men” (Jon Hamm)
3. “Ugly Betty” (Vanessa Williams)
4. “Parks and Recreation” (Nick Offerman)
5. “The Simpsons” (“Mr. Burns” voiced by Harry Shearer)