Movies like Sideways (2009)
The best movies like Sideways (2009) are A Nice Girl Like You (2020), Yoh! Bestie (2026) and Girl on a Bicycle (2013). If Sideways hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest rated¿Quieres ser mi hijo? (2023)8.4/10 from 378 votes
- NewestYoh! Bestie (2026)Released 2026
A Nice Girl Like You (2020)
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey of self-discovery, friendship, and new love.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisYoh! Bestie (2026)
Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisGirl on a Bicycle (2013)
Paolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French woman on a bicycle the very next day turns Paolo's life upside down.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisLove, Weddings & Other Disasters (2020)
A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisSex Appeal (2022)
Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisWhat's Love Got to Do with It? (2023)
Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Prince & Me 4: The Elephant Adventure (2010)
One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged marriage to the brooding and sinister Kah and is secretly in love with a young elephant handler named Alu.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisLittle Italy (2018)
Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisPlaying It Cool (2014)
A young man meets and instantly falls in love with an engaged woman.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisMy Sassy Girl (2008)
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisDesperados (2020)
A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like this¿Quieres ser mi hijo? (2023)
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Absolute CinemaMovies like thisThe Incredible Jessica James (2017)
Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisI Want You Back (2022)
Peter and Emma thought they were on the precipice of life’s biggest moments – marriage, kids, and houses in the suburbs – until their respective partners dumped them. Horrified to learn that the loves of their lives have already moved on, Peter and Emma hatch a hilarious plan to win back their exes with unexpected results.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies 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 thisThe Right Kind of Wrong (2013)
A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisLet's Make Love (1960)
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisWatching the Detectives (2007)
Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets turned upside down and the line between reality and the movies quickly begins to blur.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisCuban Fury (2014)
Beneath Bruce Garrett's under-confident, overweight exterior, the passionate heart of a salsa king lies dormant. Now, one woman is about to reignite his Latin fire.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisI Love You Again (1940)
Boring businessman Larry Wilson recovers from amnesia and discovers he's really a con man...and loves his soon-to-be-ex wife.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisAlfie (2004)
A tale of a philosophical womanizer who is forced to question his seemingly carefree existence.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisThe Out-of-Towners (1999)
The adventures of married couple Henry and Nancy Clark, vexed by misfortune while in New York City for Henry's job interview.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisYennamo Yedho (2014)
Gautham and Nithya become friends after their respective partners ditch them to get married. Friendship turns to love for Gautham but things turn complicated when Nithya gets engaged to Raja. She calls off the engagement but now, he is in a rebound relationship with Kavya. Will the two express their love for each other?
Why it matches: Similar story and style · both romance & comedy
Sweet 20 (2017)
Adapted from Korean movie, Miss Granny, this movie tells a story of old woman that despise old-age that suddenly transform to a pretty girl with all her youth problems.
Why it matches: Similar story and style · both comedy
Welcome to Collinwood (2002)
Five hapless inner-city low-lifes attempt to burgle a pawnbroker's safe, but end up being plagued by bad luck.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThe Longest Yard (2005)
Disgraced pro football quarterback Paul Crewe lands in a Texas federal penitentiary, where manipulative Warden Hazen recruits him to advise the institution's football team of prison guards. Crewe suggests a tune-up game which lands him quarterbacking a crew of inmates in a game against the guards. Aided by incarcerated ex-NFL coach and player Nate Scarborough, Crewe and his team must overcome not only the bloodthirstiness of the opposition, but also the corrupt warden trying to fix the game against them.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThe Taking of Pelham One Two Three (1974)
In New York, armed men hijack a subway car and demand a ransom for the passengers while the authorities question about the method of their escape.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisWild Wild West (1999)
Legless Southern inventor Dr. Arliss Loveless plans to rekindle the Civil War by assassinating President Ulysses S. Grant. Only two men can stop him: gunfighter James West and master-of-disguise and inventor Artemus Gordon. The two must team up to thwart Loveless' plans.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisStreetwalker (1970)
A roughneck music hall owner grooms a charmnig yet haggard belly dancer to be his new star headliner, but she falls in love with a pianist also in his employ.
Why it matches: Similar story and style · both romance
Always (1989)
The spirit of a recently deceased expert pilot mentors a newer pilot while watching him fall in love with the girlfriend that he left behind.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like this
Like Sideways and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Sideways?
The closest matches to Sideways are A Nice Girl Like You (2020), Yoh! Bestie (2026) and Girl on a Bicycle (2013). Below are 27 more, each with the reason it matches.
What should I watch after Sideways?
Start with A Nice Girl Like You (2020), the closest match to Sideways.
What is the highest-rated movie like Sideways?
¿Quieres ser mi hijo? (2023), rated 8.4/10 by 378 TMDB users.
What is the newest movie like Sideways?
Yoh! Bestie (2026) is the most recent release on this list.
Are there Japanese movies like Sideways?
The closest matches are in other languages.
How are movies similar to Sideways chosen?
First come films that Trakt’s viewers watch alongside Sideways, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.