Movies like You're The Boss! (1985)
The best movies like You're The Boss! (1985) are Cruel Intentions (1999), She's the Man (2006) and The King of Marvin Gardens (1972). If You're The Boss! hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedHello, Dolly! (1969)7.0/10 from 409 votes
- NewestSpa Weekend (2026)Released 2026
Cruel Intentions (1999)
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 loses, Kathryn will claim his most prized possession.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisShe's the Man (2006)
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 beautiful Olivia, who has fallen for Sebastian! As if that were not enough, Viola's twin returns from London ahead of schedule but has no idea that his sister has already replaced him on campus.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe King of Marvin Gardens (1972)
Jason Staebler lives on the Boardwalk and fronts for the local mob in Atlantic City. He is a dreamer who asks his brother David, a radio personality from Philadelphia, to help him build a paradise on a Pacific Island, which might be just another of his pie-in-the-sky schemes. Inevitably, complications begin to pile up.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisLike a Boss (2020)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSpa Weekend (2026)
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, the women escape to a luxury spa retreat for an unforgettable weekend dedicated to fun, laughter, and a lot of really bad decisions.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisFired Up! (2009)
Popular high schoolers and best friends Shawn and Nick decide to ditch football camp for cheerleader camp. For the girls and for the glory.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Ladies Man (1961)
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 all these females?
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisDeliver Us from Eva (2003)
Eva Dandridge has been in charge of her younger sisters ever since their parents died many years ago. She is a very uptight young woman who constantly meddles in the affairs of her sisters and their significant others. Her brothers-in-law, who are tired of Eva interfering in their lives, decide to set her up with someone so she can leave them alone. They end up paying Ray, the local "playboy," $5,000 to date her. The plan goes by smoothly, but trouble comes when Ray actually falls in love with Eva.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisGood Advice (2001)
An investment banker loses everything and must discover what's really important in life.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisOne of Them Days (2025)
When one roommate's boyfriend blows their rent money, two best friends embark on a chaotic race against time to avoid eviction while trying to keep their friendship intact.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSextuplets (2019)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisHello, Dolly! (1969)
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 intended, and Horace's two clerks to travel to New York City.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisJoe's Apartment (1996)
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.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisThe Underdoggs (2024)
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 as an opportunity to rebuild his public image. But in the process, he may just turn his life around and rediscover his love of the game.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisThe Matchmaker's Playbook (2018)
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 when Blake Olson requests the services of Wingmen, Inc., Ian may have landed his most hopeless client yet. As Blake begins the transformation from hot mess to smokin' hot, Ian realizes he's in danger of breaking his cardinal rule....
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisHow to Lose a Guy in 10 Days (2003)
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 running in this irresistible tale of sex, lies and outrageous romantic fireworks!
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisIn the Good Old Summertime (1949)
Two co-workers in a music shop dislike one another during business hours but unwittingly carry on an anonymous romance through the mail.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like this40 Dates and 40 Nights (2026)
Ready to quit the dating scene altogether, burned-out Leah accepts her grandmother's outrageous challenge—40 dates in 40 nights in exchange for a year's rent—only to discover amidst the awkward dinners and unexpected sparks that her biggest obstacle to love is herself.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisSomeone Like You... (2001)
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 begins an extensive study of the male animal, including her womanizing roommate Eddie. Jane puts her studies and romantic misadventure to use as a pseudonymous sex columnist -- and becomes a sensation.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisRoommates (2026)
When shy college freshman Devon asks cool-girl Celeste to be her roommate, a blossoming friendship quickly spirals into a war of passive aggression.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like You're The Boss!?
The closest matches to You're The Boss! are Cruel Intentions (1999), She's the Man (2006) and The King of Marvin Gardens (1972). Below are 17 more, each with the reason it matches.
What should I watch after You're The Boss!?
Start with Cruel Intentions (1999), the closest match to You're The Boss!.
What is the highest-rated movie like You're The Boss!?
Hello, Dolly! (1969), rated 7.0/10 by 409 TMDB users.
What is the newest movie like You're The Boss!?
Spa Weekend (2026) is the most recent release on this list.
Are there English movies like You're The Boss!?
Yes: Cruel Intentions (1999), She's the Man (2006) and The King of Marvin Gardens (1972).
How are movies similar to You're The Boss! chosen?
First come films that Trakt’s viewers watch alongside You're The Boss!, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.