Movies like You're the Boss (2023)
The best movies like You're the Boss (2023) are Chief Daddy 2: Going for Broke (2021), Billy Madison (1995) and Thunderstruck (2012). If You're the Boss hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedThe Willoughbys (2020)7.1/10 from 1,037 votes
- NewestDriver's Ed (2026)Released 2026
Chief Daddy 2: Going for Broke (2021)
The Beecroft family are ready to spend all of Chief Daddy's inheritance, but not if the CEO of his company has anything to do with it.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBilly Madison (1995)
Billy Madison is the 27 year-old son of Bryan Madison, a very rich man who has made his living in the hotel industry. Billy stands to inherit his father's empire, but only if he can make it through all 12 grades, 2 weeks per grade, to prove that he has what it takes to run the family business.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThunderstruck (2012)
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Roast of Tom Brady (2024)
Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisClass Rank (2017)
Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn a thing or two about love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Wedding Year (2019)
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisSneakerella (2022)
When El, an aspiring sneaker designer from Queens, meets Kira King, the fiercely independent daughter of legendary basketball star and sneaker tycoon Darius King, sparks fly as the two bond over their mutual affinity for sneakers. With a little nudge from his best friend and a sprinkle of Fairy Godfather magic, El finds the courage to use his talent to pursue his dream of becoming a ‘legit’ sneaker designer in the industry.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisLittle Big League (1994)
When the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take orders from a 12-year-old.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisPsych 2: Lassie Come Home (2020)
After Santa Barbara Police Chief Carlton Lassiter is ambushed and left for dead, Shawn and Gus return to help him and find themselves embroiled in a case involving the personal, the professional – and even the supernatural.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Trouble with Angels (1966)
Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and their unpleasant classmates, becoming a constant thorn in Mother Superior's side. However, as the years pass, Mary and Rachel slowly mature and begin to see the nuns in a different light.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Willoughbys (2020)
When the four Willoughby children are abandoned by their selfish parents, they must learn how to adapt their Old-Fashioned values to the contemporary world in order to create something new: The Modern Family.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisClear History (2013)
Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDriver's Ed (2026)
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisI Love My Dad (2022)
A hopelessly estranged father catfishes his son in an attempt to reconnect.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisThe Pink Panther Strikes Again (1976)
Charles Dreyfus, who has finally cracked over inspector Clouseau's antics, escapes from a mental institution and launches an elaborate plan to get rid of Clouseau once and for all.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 · both comedy
Popcorn FlickMovies like thisCorner Gas: The Movie (2014)
It’s been a few years, and there’s still not a lot going on 40 kilometers from nowhere. But that’s all about to change as the fine folks of Dog River, Saskatchewan face their biggest crisis ever. Brent and the gang discover that the town’s been badly mismanaged, leaving residents with little choice but to pack up and leave. As residents make one last rally to save Dog River as they know it, they discover a devious plan by a corporate chain that would change life for Dog Riverites forever.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCadet Kelly (2002)
Hyperactive teenager Kelly is enrolled into a military school when her new stepfather becomes the Commandant. At first she has problems fitting in and taking orders until she tries out for the drill team.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAli Wong: Single Lady (2024)
After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJoy Ride (2023)
When Audrey's business trip to Asia goes sideways, she enlists the aid of Lolo, her irreverent, childhood best friend who also happens to be a hot mess; Kat, her college friend turned Chinese soap star; and Deadeye, Lolo's eccentric cousin. Their no-holds-barred, epic experience becomes a journey of bonding, friendship, belonging, and wild debauchery that reveals the universal truth of what it means to know and love who you are.
Why it matches: Recommended by TMDB viewers · both comedy
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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 Chief Daddy 2: Going for Broke (2021), Billy Madison (1995) and Thunderstruck (2012). Below are 17 more, each with the reason it matches.
What should I watch after You're the Boss?
Start with Chief Daddy 2: Going for Broke (2021), the closest match to You're the Boss.
What is the highest-rated movie like You're the Boss?
The Willoughbys (2020), rated 7.1/10 by 1,037 TMDB users.
What is the newest movie like You're the Boss?
Driver's Ed (2026) is the most recent release on this list.
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.