Movies like The Boss's Daughter (2016)
The best movies like The Boss's Daughter (2016) are Which Brings Me to You (2023), A California Christmas: City Lights (2021) and The Other Sister (1999). If The Boss's Daughter hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedThe Apartment (1960)8.2/10 from 2,848 votes
- NewestHe Loves Me Not (2026)Released 2026
- In FrenchMoliere (2007)Also in French
Which Brings Me to You (2023)
Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of messy histories and heartbreak, on the off chance that this fling might be the real thing.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisA California Christmas: City Lights (2021)
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Other Sister (1999)
A mentally challenged girl proves herself to be every bit as capable as her "perfect" sister when she moves into an apartment and begins going to college.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisCosi (1996)
Lewis, a young amateur theater director, is offered a job with a governmental program for the rehabilitation of mentally ill patients in a Sydney institution. His project is overrun by one of the patients, who wants to stage the opera Cosi Fan Tutte by Mozart, despite the fact that none of the patients can sing or speak Italian. A comedy of errors ensues, but one which unifies the patients and their director in unexpected ways.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisHe Said, She Said (1991)
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisA California Christmas (2020)
With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisMoliere (2007)
Molière, a down-and-out actor-cum-playwright up to his ears in debt. When the wealthy Jourdain offers to cover that debt so that Molière's theatrical talents might help Jourdain win the heart of a certain widowed marquise, hilarity ensues.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisHappiness for Beginners (2023)
At a crossroads after her divorce, a schoolteacher ventures toward a fresh start in life — and love — when she signs up for a grueling group hiking trip.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLove Is Overrated (2025)
Diagnosed «crap with girls» by his friends, Anis’ love life has barely a pulse. Three years after the loss of Isma, his best friend and mentor, Anis takes his courage in both hands and decides finally to get out and meet people again. And the person he meets is Madeleine. Thinking she’s way out of his league, Anis gets tangled in a web of silly lies trying to impress her. But something huge is about to start. An unexpected thing. A thing called love.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisAnother Woman's Life (2012)
When the fun loving Marie sets her eyes on brooding comic book artist Paul, it sets off the kind of romantic sparks that quickly culminate in the bedroom. But the next morning brings its share of surprises as Marie crawls out of bed to discover her life flash-forwarded fifteen years down the road: Not only has she been married to Paul all this time, but she’s now the mother of a little boy the head of a powerful multinational investment firm and the proprietor of a fabulous apartment overlooking the Eiffel Tower. Quickly Marie discovers that all her achievements have not brought happiness.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisL.A. Without a Map (1999)
An aspiring Hollywood actress, on a visit to a charming North England town, has a brief fling with the town undertaker, who also writes obituaries for the local paper. Returning home, where she works as a waitress at a Japanese restaurant, she tells everyone about the handsome "writer" she met on her trip. Unfortunately, he decides to follow her back to Hollywood, setting up the expected light romantic comedy with asides as the newcomer gains experience about the goings on in Hollywood.
Why it matches: Recommended by TMDB viewers · both drama & comedy
SnoozefestMovies like thisSidewalks of New York (2001)
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisThe Baltimorons (2025)
A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisLove in Taipei (2023)
A young American woman is sent by her parents to a cultural immersion program in Taipei where she begins a new journey of self-discovery and romance.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisOnce Around (1991)
A struggling woman finds unexpected love with a charismatic older salesman at a real estate seminar. Their passionate relationship clashes with the values of her family, particularly her father.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisHitch (2005)
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisI Met a Girl (2020)
An aspiring musician struggling with schizophrenia falls for a mysterious woman who may be all in his head. When she suddenly vanishes, he takes off on a cross-country journey across Australia to find her, forcing his long-suffering brother to chase after him.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisMarius (1931)
César runs a bar along Marseilles' port, assisted by his 23-year-old son, Marius. Friends since childhood, Fanny and Marius love each other, but Marius has a secret wanderlust: every ship's whistle stirs a longing for foreign lands. When M. Panisse seeks Fanny's hand in marriage and when a departing clipper needs a deckhand, Marius and Fanny must decide who and what they love most. César, with his generous, wise spirit, tries to guide his son.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisLove Is in the Air (2023)
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisRelationship Goals (2026)
When TV producer Leah Caldwell aims to become the first woman running New York's top morning show, her ex competes for the same role. Leah stays focused on her career, until chemistry with her ex challenges her priorities.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Apartment (1960)
Bud Baxter is a minor clerk in a huge New York insurance company, until he discovers a quick way to climb the corporate ladder. He lends out his apartment to the executives as a place to take their mistresses. Although he often has to deal with the aftermath of their visits, one night he's left with a major problem to solve.
Why it matches: Similar story and style · both comedy & drama
Absolute CinemaMovies like thisChocolat (2000)
In the winter of 1959, a single mother and her young daughter arrive in a rural French town, where they open an unusual chocolate shop that disrupts the moral fiber of the strictly Catholic townsfolk and mayor.
Why it matches: Similar story and style · both comedy & drama
Worth the HypeMovies like thisFools Rush In (1997)
After a one night stand with Alex, Isabel realizes that she is pregnant and they decide to get married. However, along with the marriage comes compromise of one's own cultural traditions.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisCasablanca (1943)
In Casablanca, Morocco in December 1941, a cynical American expatriate meets a former lover, with unforeseen complications.
Why it matches: Similar story and style · both drama & romance
Absolute CinemaMovies like thisBewitched (2021)
It's more dificult to love than to be bewitched. The film has as it's central theme the loving separation, but the consequences of this separation are attributed to occult forces that throwing the protagonist in the world of Afro-Brazilian mystical religions.
Why it matches: Similar story and style · both comedy & romance
Notting Hill (1999)
London bookstore owner William Thacker's quiet life turns upside down when a chance encounter with famous actress Anna Scott sparks an unlikely romance challenged by their vastly different worlds.
Why it matches: Similar story and style · both romance & comedy
Worth the HypeMovies like this50 First Dates (2004)
Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and again. That's because the delightful Lucy has no short-term memory, so Henry must woo her day after day until he finally sweeps her off her feet.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisThe Wedding Planner (2001)
San Francisco's premiere wedding planner, Mary Fiore is rescued from an accident by the man of her dreams, pediatrician Steve Edison, only to find he is the fiancé of her latest client. As Mary continues making their wedding arrangements, she and Steve are put into a string of uncomfortable situations that force them to face their mutual attraction.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like this2 Days in Paris (2007)
Marion and Jack try to rekindle their relationship with a visit to Paris, home of Marion's parents — and several of her ex-boyfriends.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisHe Loves Me Not (2026)
An aspiring actress chosen as a wild card for a reality TV dating show uses a secret elixir to win the heart of the star, but when her deception is revealed, she discovers a messy but real chance for love.
Why it matches: Similar story and style · both romance & comedy
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Frequently asked questions
What are the best movies like The Boss's Daughter?
The closest matches to The Boss's Daughter are Which Brings Me to You (2023), A California Christmas: City Lights (2021) and The Other Sister (1999). Below are 27 more, each with the reason it matches.
What should I watch after The Boss's Daughter?
Start with Which Brings Me to You (2023), the closest match to The Boss's Daughter.
What is the highest-rated movie like The Boss's Daughter?
The Apartment (1960), rated 8.2/10 by 2,848 TMDB users.
What is the newest movie like The Boss's Daughter?
He Loves Me Not (2026) is the most recent release on this list.
Are there French movies like The Boss's Daughter?
Yes: Moliere (2007), Love Is Overrated (2025) and Another Woman's Life (2012).
How are movies similar to The Boss's Daughter chosen?
First come films that Trakt’s viewers watch alongside The Boss's Daughter, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.