If you've ever had a boss that made you laugh or cringe, these films are for you. This collection showcases the lighter side of workplace dynamics, where bosses are either the source of comedy or the butt of the joke. Whether it's their incompetence, their tyranny, or their sheer absurdity, these films will give you a good chuckle while perhaps reminding you of your own office experiences.

Nine to Five (1980)
Description: Three female office workers fantasize about getting rid of their sexist, egotistical boss, leading to a series of comedic events. This film was groundbreaking for its time, highlighting workplace sexism with humor.
Fact: The film's theme song became a hit, and the movie itself inspired a TV series.


The Secret of My Success (1987)
Description: Michael J. Fox plays a young man who, after being fired from his first job, impersonates an executive at his uncle's company. The film is a comedic exploration of ambition and the corporate ladder.
Fact: The film's title was changed from "The Secret of My Succe$s" to avoid confusion with another film.


Working Girl (1988)
Description: A secretary, played by Melanie Griffith, seizes an opportunity to advance her career when her boss is incapacitated, leading to a series of comedic and dramatic events. The film humorously portrays the struggle to succeed in a male-dominated corporate world.
Fact: The film was nominated for six Academy Awards, including Best Picture.


Office Space (1999)
Description: A classic satire on corporate culture, where an employee's frustration with his job and his boss leads to a plan to defraud the company. The film's portrayal of the mundane office life and the boss, Bill Lumbergh, has become iconic.
Fact: The character of Milton Waddams was inspired by a real-life office worker who was constantly moved around the office.


The Devil Wears Prada (2006)
Description: A young journalist lands a job at a high-fashion magazine, only to find her boss, played by Meryl Streep, is a demanding and terrifying figure. The film humorously explores the dynamics between a boss and her assistant.
Fact: Meryl Streep based her character on Vogue editor Anna Wintour, who reportedly loved the film.


Horrible Bosses (2011)
Description: Three friends conspire to murder their intolerable bosses, leading to a series of comedic misadventures. This film perfectly encapsulates the frustration of dealing with terrible bosses, making it a must-watch for anyone who's ever fantasized about getting even.
Fact: The film was so successful it spawned a sequel, "Horrible Bosses


The Internship (2013)
Description: Two middle-aged salesmen, played by Vince Vaughn and Owen Wilson, secure internships at Google, dealing with young, tech-savvy interns and their own out-of-touch boss. This film is a comedic look at generational differences in the workplace.
Fact: Google allowed the film to be shot on their campus, providing a realistic backdrop for the story.


The Intern (2015)
Description: Robert De Niro plays a 70-year-old widower who becomes an intern at a fashion website, dealing with a young, dynamic CEO played by Anne Hathaway. This film offers a unique take on the boss-employee relationship, with humor and heart.
Fact: The film was inspired by a real-life program at a tech company where older interns were brought in to share their life experiences.


The Boss (2016)
Description: Melissa McCarthy stars as a ruthless businesswoman who, after being released from prison, must rebuild her empire with the help of her former assistant. This film captures the essence of a boss who's both hilariously over-the-top and endearing.
Fact: The film was originally titled "Michelle Darnell," which was McCarthy's character's name.


Up in the Air (2009)
Description: George Clooney plays a corporate downsizer who travels the country firing people, until a new hire threatens his lifestyle. While not strictly a comedy, the film has humorous moments and deals with the boss-employee relationship in a unique way.
Fact: The film was adapted from a novel by Walter Kirn, and the screenplay was nominated for an Academy Award.
