Movies like Sideways
The best movies like Sideways (2004) are Youth in Revolt (2009), Ruby Sparks (2012) and Enemies, a Love Story (1989). If Sideways 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 ratedApocalypse Now (1979)8.3/10 from 9,532 votes
- NewestThe Last Sunrise (2026)Released 2026
Youth in Revolt (2009)
As a fan of Albert Camus and Jean-Luc Godard, teenage Nick Twisp is definitely out of his element when his mother and her boyfriend move the family to a trailer park. When a pretty neighbor named Sheeni plays records by French crooners, it's love at first sight for frustrated and inexperienced Nick. Learning that she is dating someone, Nick launches a hilarious quest to find his way into Sheeni's heart -- and bed.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisRuby Sparks (2012)
Calvin is a young novelist who achieved phenomenal success early in his career but is now struggling with his writing – as well as his romantic life. Finally, he makes a breakthrough and creates a character named Ruby who inspires him. When Calvin finds Ruby, in the flesh, sitting on his couch about a week later, he is completely flabbergasted that his words have turned into a living, breathing person.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisEnemies, a Love Story (1989)
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisIn the Land of Women (2007)
After a bad breakup with his girlfriend leaves him heartbroken, Carter Webb moves to Michigan to take care of his ailing grandmother. Once there, he gets mixed up in the lives of the mother and daughters who live across the street.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisLove & Sex (2000)
When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.
Why it matches: Recommended by TMDB viewers · both comedy & drama
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 thisThe Sisters Brothers (2018)
Oregon, 1851. Hermann Kermit Warm, a chemist and aspiring gold prospector, keeps a profitable secret that the Commodore wants to know, so he sends the Sisters brothers, two notorious assassins, to capture him on his way to California.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisInherent Vice (2014)
In Los Angeles at the turn of the 1970s, drug-fueled detective Larry "Doc" Sportello investigates the disappearance of an ex-girlfriend.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisA 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 thisTom Jones (1963)
Tom loves Sophie and Sophie loves Tom. But Tom and Sophie are of differering classes. Can they find a way through the mayhem to be true to love?
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisAfter Everything (2023)
Besieged by writer’s block and the crushing breakup with Tessa, Hardin travels to Portugal in search of a woman he wronged in the past – and to find himself. Hoping to win back Tessa, he realizes he needs to change his ways before he can make the ultimate commitment.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisLooking: The Movie (2016)
Patrick returns to San Francisco for the first time in almost a year to celebrate a momentous event with his old friends. In the process, he must face the unresolved relationships he left behind and make difficult choices about what’s important to him.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisSmoke (1995)
Writer Paul Benjamin is nearly hit by a bus when he leaves Auggie Wren's smoke shop. Stranger Rashid Cole saves his life, and soon middle-aged Paul tells homeless Rashid that he wouldn't mind a short-term housemate. Still grieving over his wife's murder, Paul is moved by both Rashid's quest to reconnect with his father and Auggie's discovery that a woman who might be his daughter is about to give birth.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisThe Clique (2008)
A young girl tries to fit in with a clique of popular middle school girls after moving into the guest house of one of their homes.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisFear and Loathing in Las Vegas (1998)
Raoul Duke and his attorney Dr. Gonzo drive a red convertible across the Mojave desert to Las Vegas with a suitcase full of drugs to cover a motorcycle race. As their consumption of drugs increases at an alarming rate, the stoned duo trash their hotel room and fear legal repercussions. Duke begins to drive back to L.A., but after an odd run-in with a cop, he returns to Sin City and continues his wild drug binge.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Worth the HypeMovies like thisLove Me Love Me (2026)
After her brother's death, June moves to Milan for a fresh start, finding comfort in Will, the perfect honor student at her new international school. But when his troubled best friend James—hiding a dangerous life in clandestine MMA fights—sparks a rivalry that quickly turns into irresistible attraction, June must choose between safety and a love that upends everything she thought she wanted.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisThe Last Sunrise (2026)
Ry, a college student with a chronic illness, escapes to Mallorca for the summer with her mother, where she unexpectedly falls for a local and begins to embrace living in the moment. But as her condition worsens and long-hidden family secrets come to light, everything she has found before summer's end is threatened.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisBarton Fink (1991)
A renowned New York playwright is enticed to California to write for the movies and discovers the hellish truth of Hollywood.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisBlind (2017)
A novelist is blinded in a car crash that killed his wife and several years later rediscovers his passion for life and writing when he embarks on an affair with the neglected wife of an indicted businessman.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisHow to Be Single (2016)
New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisAbout a Boy (2002)
Will Freeman is a good-looking, smooth-talking bachelor whose primary goal in life is avoiding any kind of responsibility. But when he invents an imaginary son in order to meet attractive single moms, Will gets a hilarious lesson about life from a bright, but hopelessly geeky 12-year-old named Marcus. Now, as Will struggles to teach Marcus the art of being cool, Marcus teaches Will that you're never too old to grow up.
Why it matches: Similar story and style · both drama & comedy
Popcorn FlickMovies like thisThe Elementary Particles (2006)
Based on Michel Houellebecq's controversial novel, Atomised (aka The Elementary Particles) focuses on Michael and Bruno, two very different half-brothers and their disturbed sexuality. After a chaotic childhood with a hippie mother only caring for her affairs, Michael, a molecular biologist, is more interested in genes than women, while Bruno is obsessed with his sexual desires, but mostly finds his satisfaction with prostitutes. But Bruno's life changes when he gets to know the experienced Christiane. In the meantime, Michael meets Annabelle, the love of his youth, again.
Why it matches: Similar story and style · both drama & romance
Popcorn FlickMovies like thisThe Wizard (1989)
A boy and his brother run away from home and hitch cross-country, with help from a girl they meet, to compete in the ultimate video game championship.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisBlade Runner (1982)
In the smog-choked dystopian Los Angeles of 2019, blade runner Rick Deckard is called out of retirement to terminate a quartet of replicants who have escaped to Earth seeking their creator for a way to extend their short life spans.
Why it matches: Similar story and style · both drama
Absolute CinemaMovies like thisAnatomy of a Murder (1959)
Semi-retired Michigan lawyer Paul Biegler takes the case of Army Lt. Manion, who murdered a local innkeeper after his wife claimed that he raped her. Over the course of an extensive trial, Biegler parries with District Attorney Lodwick and out-of-town prosecutor Claude Dancer to set his client free, but his case rests on the victim's mysterious business partner, who's hiding a dark secret.
Why it matches: Similar story and style · both drama
Worth the HypeMovies like thisBeverly Hills Cop II (1987)
Axel Foley returns to the land of sunshine and palm trees to investigate the near-fatal shooting of police Captain Andrew Bogomil. With the help of Sgt. Taggart and Det. Rosewood, they soon uncover that the shooting is associated with a series of "alphabet" robberies masterminded by a heartless weapons kingpin—and the chase is on.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisJarhead (2005)
Jarhead is a film about a US Marine Anthony Swofford’s experience in the Gulf War. After putting up with an arduous boot camp, Swofford and his unit are sent to the Persian Gulf where they are eager to fight, but are forced to stay back from the action. Swofford struggles with the possibility of his girlfriend cheating on him, and as his mental state deteriorates, his desire to kill increases.
Why it matches: Similar story and style · both drama
Popcorn FlickMovies like thisApocalypse Now (1979)
At the height of the Vietnam war, Captain Benjamin Willard is sent on a dangerous mission that, officially, "does not exist, nor will it ever exist." His goal is to locate - and eliminate - a mysterious Green Beret Colonel named Walter Kurtz, who has been leading his personal army on illegal guerrilla missions into enemy territory.
Why it matches: Similar story and style · both drama
Absolute CinemaMovies like thisThe Simpsons Movie (2007)
After Homer accidentally pollutes the town's water supply, Springfield is encased in a gigantic dome by the EPA and the Simpsons are declared fugitives.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisAbsolute Power (1997)
A master thief coincidentally is robbing a house where a murder—in which the President of the United States is involved—occurs in front of his eyes. He is forced to run, while holding evidence that could convict the President.
Why it matches: Similar story and style · both drama
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Sideways?
The closest matches to Sideways are Youth in Revolt (2009), Ruby Sparks (2012) and Enemies, a Love Story (1989). Below are 27 more, each with the reason it matches.
What should I watch after Sideways?
Start with Youth in Revolt (2009), the closest match to Sideways.
What is the highest-rated movie like Sideways?
Apocalypse Now (1979), rated 8.3/10 by 9,532 TMDB users.
What is the newest movie like Sideways?
The Last Sunrise (2026) is the most recent release on this list.
Are there English movies like Sideways?
Yes: Youth in Revolt (2009), Ruby Sparks (2012) and Enemies, a Love Story (1989).
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.