10 Hilarious Films About Bosses

10 Hilarious Films About Bosses Workplace Comedies

In the world of cinema, bosses have often been portrayed as the epitome of stress, incompetence, or sheer hilarity. This curated list of comedy films about bosses offers a delightful escape into the lives of those who lead with a comedic twist. Whether they're bumbling, tyrannical, or just plain quirky, these characters provide endless entertainment. From classic office satires to modern workplace comedies, this collection promises laughter, relatable moments, and perhaps a few lessons on what not to do when you're in charge.

Nine to Five (1980)
TRAILER

Nine to Five (1980)

Description: Three female office workers fantasize about getting rid of their sexist, egotistical boss, leading to a series of comedic and empowering events. This film is a classic in workplace comedy.

Fact: The film was inspired by a 9 to 5 organization advocating for women's rights in the workplace. Dolly Parton wrote the theme song, which became a hit.

Amazon Prime Video Watch Now
The Secret of My Success (1987)
TRAILER

The Secret of My Success (1987)

Description: Michael J. Fox plays a young man who, after losing his job, pretends to be an executive at a company, leading to a series of comedic mishaps and a satirical look at corporate culture.

Fact: The film was originally titled "The Secret of My Succe$s," with the dollar sign in the title. Fox's character's name, Brantley Foster, was a nod to the film's producer.

Amazon Prime Video Watch Now
Office Space (1999)
TRAILER

Office Space (1999)

Description: This film captures the essence of office life with its portrayal of Peter Gibbons, who, after hypnosis, decides to slack off at work, leading to a series of comedic events. It's a must-watch for anyone who's ever had a boss they love to hate.

Fact: The TPS reports and the character of Bill Lumbergh have become iconic symbols of office culture. The film was inspired by Mike Judge's own experiences in the tech industry.

Amazon Prime Video Watch Now
The Devil Wears Prada (2006)
TRAILER

The Devil Wears Prada (2006)

Description: While not strictly a comedy, the film's portrayal of the ruthless magazine editor Miranda Priestly, played by Meryl Streep, provides plenty of comedic moments amidst the fashion world's chaos.

Fact: Meryl Streep's performance was so convincing that many believed she was channeling real-life Vogue editor Anna Wintour. The film's title is a play on the phrase "the devil wears Prada," referring to the high fashion industry.

Amazon Prime Video Watch Now
Horrible Bosses (2011)
TRAILER

Horrible Bosses (2011)

Description: Three friends, fed up with their intolerable bosses, hatch a plan to murder them. The film's humor comes from the absurdity of their situation and the lengths they go to avoid their bosses' wrath.

Fact: The film was so successful that it spawned a sequel, "Horrible Bosses 2," released in

Amazon Prime Video Watch Now
The Big Short (2015)
TRAILER

The Big Short (2015)

Description: This film, while dealing with the serious subject of the 2008 financial crisis, uses humor and unconventional narrative techniques to make the complex world of finance accessible and entertaining.

Fact: The film breaks the fourth wall with celebrities explaining financial terms, making it both educational and humorous. It was based on the non-fiction book by Michael Lewis.

Amazon Prime Video Watch Now
The Intern (2015)
TRAILER

The Intern (2015)

Description: Robert De Niro plays a 70-year-old widower who becomes an intern at a fashion startup run by Anne Hathaway's character. The generational clash and mentorship themes provide plenty of laughs.

Fact: The film was inspired by a real-life program at a tech startup where older interns were brought in to share their wisdom. De Niro's character was based on a real person.

Amazon Prime Video Watch Now
The Boss (2016)
TRAILER

The Boss (2016)

Description: Melissa McCarthy plays a ruthless businesswoman who, after being sent to prison, must rebuild her empire with the help of her former assistant. The film's humor comes from McCarthy's over-the-top performance.

Fact: McCarthy co-wrote the film with her husband, Ben Falcone, who also directed it. The character was inspired by real-life business tycoons.

Amazon Prime Video Watch Now
Up in the Air (2009)
TRAILER

Up in the Air (2009)

Description: While not strictly a comedy, George Clooney's character, Ryan Bingham, who fires people for a living, provides dark humor and insights into corporate America's downsizing culture.

Fact: The film was based on a novel by Walter Kirn. Clooney's character was inspired by real-life corporate downsizers.

Amazon Prime Video Watch Now
The Internship (2013)
TRAILER

The Internship (2013)

Description: Two middle-aged salesmen, played by Vince Vaughn and Owen Wilson, land internships at Google, leading to a comedic clash of generations and corporate culture.

Fact: Google allowed filming on their campus, making it one of the few films to showcase the real Googleplex. The film was criticized for its portrayal of Google's work culture.

This movie is not available on Amazon Prime, but you can use the bonus:
Amazon Prime Video 30 Days Free
Rate collection
cinepicker.com
Add a comment