Movies About Bad Bosses

Updated May 1, 2024

Multiple movies have explored Movies About Bad Bosses. Here are 14 of the best ones.

Modern Times (1936)

★★★★

3.4 out of 4 stars

From Charles Chaplin, starring Charles Chaplin, Paulette Goddard, Henry Bergman, Tiny Sandford
Rated G

Modern Times is a classic 1936 silent comedy film directed and written by Charlie Chaplin in which he stars as a factory worker, or "little tramp," struggling to survive in modern industrial society. The film follows the tramp as he is caught in the struggles between labor and capital, as well as his efforts to win the heart of a young immigrant girl. Along the way, he confronts a number of obstacles such as unemployment, unfair labor practices, and his own mental breakdown. In the end, he is able to overcome his struggles and start a new life with the girl. The film is a humorous take on the harsh realities of the Great Depression and the struggles of the working class. It is also noted for its innovative use of sound and visuals and its social commentary on the effects of rapid industrialization.

Monsters, Inc. (2001)

★★★★

3.2 out of 4 stars

From Directors: Pete Docter, David Silverman, Lee Unkrich, starring Billy Crystal, John Goodman, Mary Gibbs, Steve Buscemi
Rated G

Monsters, Inc. is an animated family comedy directed by Pete Docter, David Silverman and Lee Unkrich, released in 2001. The movie follows the adventures of two monsters, Sulley and Mike, who work at Monsters, Inc., a company responsible for scaring children. When an adventurous young girl named Boo sneaks into their world, Sulley and Mike have to protect her from the evil Randall and the CDA, while trying to get her back to her world. Along the way, they learn to care for each other, while discovering the true power of friendship and laughter.

Clerks (1994)

★★★★

3.1 out of 4 stars

From Kevin Smith, starring Brian O'Halloran, Jeff Anderson, Marilyn Ghigliotti, Lisa Spoonauer
Rated R

Clerks is a black-and-white comedy film written, directed, and produced by Kevin Smith. It follows the story of two convenience store clerks, Dante Hicks (Brian O'Halloran) and Randal Graves (Jeff Anderson), who work at a Quick Stop in Leonardo, New Jersey. The film follows a day in the lives of Dante and Randal as they talk about their lives, lament over their dead-end jobs, and insult each other and their customers. Along the way, they encounter an array of bizarre characters, including Jay (Jason Mewes) and Silent Bob (Kevin Smith), two guys who hang out at the Quick Stop. Clerks is an unconventional comedy that takes an irreverent look at work, friendship, life, and love. It is a cult classic that has become one of the most acclaimed independent films of all time.

Office Space (1999)

★★★★

3.1 out of 4 stars

From Mike Judge, starring Ron Livingston, Jennifer Aniston, David Herman, Ajay Naidu
Rated R

Office Space is a 1999 cult classic comedy directed by Mike Judge and starring Ron Livingston, Jennifer Aniston, and Stephen Root. It follows the story of Peter Gibbons, an unhappy and disgruntled office worker at Initech Corporation. After visiting a hypnotist, Peter no longer worries about pleasing his bosses and begins to voice his objections to the tedious and mundane nature of his job. His actions soon lead to him being promoted and his colleagues joining him in a plan to steal money from their employer. In the end, Peter and his fellow employees successfully steal from Initech, drastically improving their working and personal lives.