Top 10 Freelancer Comedies to Watch

Description: Although centered around office life, the film captures the essence of freelancing through Peter Gibbons' desire to escape the corporate grind and his subsequent adventures in self-employment.

Fact: The character Milton was inspired by a real-life office worker who was constantly moved around the office.

Description: Walter Mitty, a negative assets manager at Life magazine, embarks on a global adventure to find a missing photograph. His journey is filled with comedic moments as he steps out of his comfort zone, embodying the spirit of a freelancer taking on new challenges.

Fact: The film was inspired by a short story by James Thurber, but the movie's plot is quite different from the original.

Description: While not about freelancing per se, the film follows Andy Sachs, who takes on a job at a high-fashion magazine, experiencing the freelance-like nature of the fashion industry's work environment.

Fact: The film was based on a novel by Lauren Weisberger, who worked as an assistant to Vogue editor Anna Wintour.

Description: Jordan Belfort's rise and fall in the stock market world showcases a lifestyle that blurs the lines between freelancing and entrepreneurship, filled with over-the-top humor.

Fact: The film was nominated for five Academy Awards, including Best Picture.

Description: While not directly about freelancing, the film captures the essence of a group of friends taking on a "freelance" adventure in Las Vegas, with comedic results.

Fact: The film was shot in just 15 days, making it one of the fastest productions of its time.

Description: Three friends conspire to murder their awful bosses, but their plans go hilariously awry. The film touches on the freelance spirit of taking control of one's career, albeit in a very dark comedy way.

Fact: The film was initially titled "Untitled Workplace Comedy."

Description: While not strictly about freelancing, this film features characters who are essentially financial freelancers, betting against the housing market. The movie uses humor to explain complex financial concepts, making it both educational and entertaining.

Fact: The film breaks the fourth wall, with characters directly addressing the audience to explain financial jargon, adding a layer of comedy.

Description: This film follows Ben Whittaker, a 70-year-old widower, who becomes a senior intern at an online fashion site run by Jules Ostin. The dynamic between the seasoned intern and the modern, tech-savvy workplace provides plenty of comedic moments, showcasing the generational gap in freelancing.

Fact: Robert De Niro was initially hesitant to take on the role, but after reading the script, he was convinced by the unique character development.

Description: Ryan Bingham, a corporate downsizer, lives out of a suitcase, traveling the country to fire people. His lifestyle as a freelance consultant is both humorous and poignant, exploring the highs and lows of freelancing.

Fact: George Clooney learned to pack a suitcase in record time for the film, showcasing his character's efficiency.

Description: Two out-of-work salesmen, Billy and Nick, land internships at Google, where they must compete with younger, tech-savvy interns. Their lack of tech knowledge and old-school sales tactics provide plenty of laughs.

Fact: Google allowed the film crew to shoot on their campus, making the setting authentic.