Movies Like You're The Boss!

If you liked You're The Boss! (1985), a movie directed by Michael Carpenter, 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
Cruel Intentions (1999)
★ 6.8/10
Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn. But if he…
2
She's the Man (2006)
★ 6.8/10
Viola Hastings is in a real jam. Complications threaten her scheme to pose as her twin brother, Sebastian, and take his place at a new boarding school. She falls in love with her handsome roommate, Duke, who loves…
3
Spa Weekend (2026)
★ 6.5/10
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
4
Like a Boss (2020)
★ 6.2/10
Two female friends with very different ideals decide to start a beauty company together. One is more practical, while the other wants to earn her fortune and live a lavish lifestyle.
5
Fired Up! (2009)
★ 6.1/10
Popular high schoolers and best friends Shawn and Nick decide to ditch football camp for cheerleader camp. For the girls and for the glory.
6
One of Them Days (2025)
★ 6.7/10
Best friends and roommates Dreux and Alyssa are about to have One of Them Days. When they discover Alyssa’s boyfriend has blown their rent money, the duo finds themselves going to extremes in a comical race against the…
7
Sextuplets (2019)
★ 6.2/10
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
8
How to Lose a Guy in 10 Days (2003)
★ 6.9/10
It's the battle of wills, as Andie needs to prove she can dump a guy in 10 days, whereas Ben needs to prove he can win a girl in 10 days. Now, the clock is ticking—and the wildly entertaining comedy smash is off and…
9
Joe's Apartment (1996)
★ 5.8/10
A nice guy has just moved to New York and discovers that he must share his run-down apartment with a couple thousand singing, dancing cockroaches.
10
The Matchmaker's Playbook (2018)
★ 7.1/10
After a career-ending accident, former NFL recruit Ian Hunter is back on campus, and he's putting his extensive skills with women to work as one of the masterminds behind a successful and secretive dating service. But…
11
Roommates (2026)
★ 6.4/10
When shy college freshman Devon asks cool-girl Celeste to be her roommate, a blossoming friendship quickly spirals into a war of passive aggression.
12
Someone Like You... (2001)
★ 6/10
Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane…
13
Neighbors 2: Sorority Rising (2016)
★ 5.8/10
A sorority moves in next door to the home of Mac and Kelly Radner who have a young child. The Radner's enlist their former nemeses from the fraternity to help battle the raucous sisters.
14
The Hangover Part III (2013)
★ 6.2/10
This time, there's no wedding. No bachelor party. What could go wrong, right? But when the Wolfpack hits the road, all bets are off.
15
Good Advice (2001)
★ 5.9/10
An investment banker loses everything and must discover what's really important in life.
16
Hello, Dolly! (1969)
★ 7/10
Dolly Levi is a strong-willed matchmaker who travels to Yonkers, New York in order to see the miserly "well-known unmarried half-a-millionaire" Horace Vandergelder. In doing so, she convinces his niece, his niece's…
17
The Ladies Man (1961)
★ 6.3/10
After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women. Can he live in the same home with…
18
The Underdoggs (2024)
★ 7/10
Jaycen 'Two Js' Jennings is a washed-up former pro football star who has hit rock bottom. When sentenced to community service coaching the Underdoggs, an unruly pee-wee football team in his hometown, he sees it mostly…
19
The Change-Up (2011)
★ 6.2/10
Lifelong friends Dave and Mitch are envious of the other's life. Mitch thinks Dave has it all: a beautiful, loving family and a high-paying job at a prestigious law firm. But Dave thinks Mitch’s stress-free playboy…
20
Shades of Desire (2023)
★ 6.5/10
After her twin sister Aubrey goes missing, Jennifer uncovers the scandalous, secret double-life that Aubrey leads - and that has put both of them in danger.