Movies Like So You Want to Be Your Own Boss

If you liked So You Want to Be Your Own Boss (1954), a movie directed by Richard L. Bare, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Office Space (1999)
★ 7.4/10
A depressed white-collar worker tries hypnotherapy, only to find himself in a perpetual state of devil-may-care bliss that prompts him to start living by his own rules, and hatch a hapless attempt to embezzle money…
2
Tony (2026)
★ 7.4/10
A 19-year-old Anthony Bourdain travels to Provincetown and stumbles into the chaotic world of a restaurant kitchen, setting off a summer that will shape the course of his life.
3
Good Burger 2 (2023)
★ 6.3/10
Dexter Reed is down on his luck after another one of his inventions fails. Ed welcomes Dex back to Good Burger with open arms and gives him his old job back. With a new crew working at Good Burger, Dex devises a plan…
4
Lion Fist (2026)
★ 7.2/10
Martial arts fighter Joe goes to prison for four years and takes his wife's blame for a drug bust. After his release, he learns that his son needs expensive surgery because of a life-threatening tumor. Joe's only…
5
Oscar (1991)
★ 6.4/10
Angelo "Snaps" Provolone made his dying father a promise on his deathbed: he would leave the world of crime and become an honest businessman. Despite having no experience in making money in a legal fashion, Snaps sets…
6
Good Burger (1997)
★ 6.2/10
Two L.A. teens with summer jobs at Good Burger try to save their small restaurant when a corporate giant burger franchise moves in across the street.
7
Horrible Bosses (2011)
★ 6.6/10
For Nick, Kurt and Dale, the only thing that would make the daily grind more tolerable would be to grind their intolerable bosses into dust. Quitting is not an option, so, with the benefit of a few-too-many drinks and…
8
How to Succeed in Business Without Really Trying (1967)
★ 6.7/10
A young but bright former window cleaner rises to the top of his company by following the advice of a book about ruthless advancement in business.
9
Clerks (1994)
★ 7.4/10
Convenience and video store clerks Dante and Randal are sharp-witted, potty-mouthed and bored out of their minds. So in between needling customers, the counter jockeys play hockey on the roof, visit a funeral home and…
10
Broadway Danny Rose (1984)
★ 7.1/10
A hapless talent manager named Danny Rose, by helping a client, gets dragged into a love triangle involving the mob. His story is told in flashback, an anecdote shared amongst a group of comedians over lunch at New…
11
Poor Cow (1967)
★ 6.4/10
Joy lives a life filled with bad choices. At a young age, she marries and has a child–with an abusive thief who quickly ends up incarcerated. Left alone, she takes up with the guy's mate, another thief, who seems to…
12
The Breadwinner (2026)
★ 7.1/10
After his wife Katie lands a once-in-a-lifetime deal on Shark Tank that takes her on a prolonged business trip - lifelong breadwinner Nate Wilcox now has to fend for his family as a first-time stay-at-home dad.
13
Comedy Central Roast of Justin Bieber (2015)
★ 6.8/10
Several roasters, and the master himself Kevin Hart, make fun of Justin Bieber.
14
The Naked Gun (2025)
★ 6.3/10
Only one man has the particular set of skills... to lead Police Squad and save the world: Lt. Frank Drebin Jr. Following in his father's footsteps, he must solve a murder case to prevent Police Squad from closure.
15
The Three Stooges (2012)
★ 5.8/10
Left on the doorstep of an orphanage run by nuns, three newborn knuckleheads grow up to be finger-poking, nyuk-nyuking janitors named Larry, Curly and Moe. When they learn that financial problems will soon force the…
16
Hollywood Shuffle (1987)
★ 6.5/10
Aspiring actor and hot-dog stand employee Bobby Taylor catches the ire of his grandmother for auditioning for a role in the regrettably titled exploitation film "Jivetime Jimmy's Revenge." When Tinseltown Studios casts…
17
Dennis the Menace (1993)
★ 5.9/10
Mr. Wilson's ever-present annoyance comes in the form of one mischievous kid named Dennis. But he'll need Dennis's tricks to uncover a collection of gold coins that go missing when a shady drifter named Switchblade Sam…
18
Teen Titans Go! To the Movies (2018)
★ 7.2/10
All the major DC superheroes are starring in their own films, all but the Teen Titans, so Robin is determined to remedy this situation by getting over his role as a sidekick and becoming a movie star. Thus, with a few…
19
Me Time (2022)
★ 5.8/10
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
20
Fierce Creatures (1997)
★ 6.2/10
Ex-policeman Rollo Lee is sent to run Marwood Zoo, the newly acquired business of a New Zealand tycoon. In order to meet high profit targets and keep the zoo open, Rollo enforces a new 'fierce creatures' policy…