Movies like Side Out (1990)
The best movies like Side Out (1990) are Why Did I Get Married Again? (2026), My Awkward Sexual Adventure (2012) and Cyrus (2010). If Side Out 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 ratedLove Don't Co$t a Thing (2003)7.7/10 from 741 votes
- NewestWhy Did I Get Married Again? (2026)Released 2026
Why Did I Get Married Again? (2026)
The couples reunite for the destination wedding of Marcus and Angela's daughter, bringing drama old and new as they ask, "Why did we get married again?"
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisMy Awkward Sexual Adventure (2012)
A hyper-repressed and schlubby accountant (Jonas Chernick) strikes a deal with a worldly but disorganized stripper (Emily Hampshire): he'll help her with her crushing debt if she helps him become a better lover.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisCyrus (2010)
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before long, the two are locked in a battle of wits for the woman they both love-and it appears only one man can be left standing when it's over.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisHappythankyoumoreplease (2011)
Six New Yorkers navigate love, commitment, and adulthood. When struggling novelist Sam takes in an abandoned boy he meets on the subway, his life begins to intertwine with a talented singer who challenges his bachelor ways. Meanwhile, his best friend Annie battles alopecia while torn between two drastically different men, and a long-term couple faces a crossroads that could alter their future together.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisJust Before I Go (2015)
Ted Morgan has been treading water for most of his life. After his wife leaves him, Ted realizes he has nothing left to live for. Summoning the courage for one last act, Ted decides to go home and face the people he feels are responsible for creating the shell of a person he has become. But life is tricky. The more determined Ted is to confront his demons, to get closure, and to withdraw from his family, the more Ted is yanked into the chaos of their lives. So, when Ted Morgan decides to kill himself, he finds a reason to live.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisTogether Together (2021)
When young loner Anna is hired as the surrogate for Matt, a single man in his 40s, the two strangers come to realize this unexpected relationship will quickly challenge their perceptions of connection, boundaries and the particulars of love.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisIs This Thing On? (2025)
As their marriage quietly unravels, Alex faces middle age and an impending divorce, seeking new purpose in the New York comedy scene while Tess confronts the sacrifices she made for their family—forcing them to navigate co-parenting, identity, and whether love can take a new form.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisLove Don't Co$t a Thing (2003)
A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisThe Best You Can (2025)
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisFriends with Kids (2012)
In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can experience the joys of parenthood without significantly curbing their personal freedom. However, when Julie and Jason both become involved with others, they discover that they secretly harbor romantic feelings for each other.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisDelirious (2007)
Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved with K'Harma Leeds, the hottest pop star of the moment, Les grows jealous and plots revenge.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisYoung People Fucking (2007)
On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by angst and miscommunication. Mia and Eric are exes, making sure they are over each other. Jaime and Ken work together and this is a first date. Inez and Gord invite his roommate, Dave, to join them. By the time each couple has gone through a prelude, foreplay, sex, an interlude, orgasm, and afterglow, they've answered basic questions: can sex be anonymous, are we bored, is our marriage really finished, does anyone tell the truth, and how do we make someone happy?
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisNothing Like the Holidays (2008)
It’s Christmastime and the far-flung members of the Rodriguez family are converging at their parents’ home in Chicago to celebrate the season and rejoice in their youngest brother’s safe return from combat overseas.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisClass (1983)
Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the cocktail lounges of nearby Chicago, where he meets and beds the alluring Ellen, who unfortunately turns out to be Skip's mother. The division between the friends is further deepened when a cheating scandal engulfs the school.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisAmerican Pie 2 (2001)
After a year apart - attending different schools, meeting different people - the guys rent a beach house and vow to make this the best summer ever. As it turns out, whether that will happen or not has a lot to do with the girls. Between the wild parties, outrageous revelations and yes, a trip to band camp, they discover that times change and people change, but in the end, it's all about sticking together.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisEmergency (2022)
Ready for a night of legendary partying, three college students must weigh the pros and cons of calling the police when faced with an unexpected situation.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisThe Sisterhood of the Traveling Pants 2 (2008)
Four young women continue the journey toward adulthood that began with "The Sisterhood of the Traveling Pants." Now three years later, these lifelong friends embark on separate paths for their first year of college and the summer beyond, but remain in touch by sharing their experiences with each other.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisFire with Fire (1986)
A tough, street-smart kid serving a sentence in a state youth reformatory meets a beautiful, innocent girl studying at a nearby convent. When forbidden love blossoms between them, they must fight the prison authorities, their parents and the law.
Why it matches: Recommended by TMDB viewers · both drama & 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 thisWinter Spring Summer or Fall (2024)
Remi and Barnes, two very different teenagers, meet by chance in the winter of their senior year, then spend four days together over the course of a year that will change their lives forever.
Why it matches: Recommended by TMDB viewers · both romance & drama
Worth the HypeMovies like thisBlue Crush (2002)
Nothing gets between Anne Marie and her board. Living in a beach shack with three roommates, she is up before dawn every morning to conquer the waves and count the days until the Pipe Masters competition. Having transplanted herself to Hawaii with no one's blessing but her own, Anne Marie finds all she needs in the adrenaline-charged surf scene - until pro quarterback Matt Tollman comes along...
Why it matches: Similar story and style · both romance & drama
Popcorn FlickMovies like thisFree!: Timeless Medley - The Promise (2017)
The second Timeless Medley film mainly recaps Eternal Summer and a little bit of the first season. It focuses on Rin and Samezuka. It also includes new scenes and characters from High Speed.
Why it matches: Similar story and style · both comedy & drama
Against the Ropes (2004)
A fictional story inspired by North America's most famous female boxing promoter, Jackie Kallen. Her struggle to survive and succeed in a male dominated sport.
Why it matches: Similar story and style · both romance & drama
SnoozefestMovies like thisThe Karate Kid Part II (1986)
Summoned by his dying father, Miyagi returns to his homeland of Okinawa, with Daniel, after a 40-year exile. There he must confront Yukie, the love of his youth, and Sato, his former best friend turned vengeful rival. Sato is bent on a fight to the death, even if it means the destruction of their village. Daniel finds his own love in Yukia's niece, Kumiko, and his own enemy in Sato's nephew, the vicious Chozen. Now, far away from the tournaments, cheering crowds and safety of home, Daniel will face his greatest challenge ever when the cost of honor is life itself.
Why it matches: Similar story and style · both drama & romance
Popcorn FlickMovies like thisDog Days (2001)
Vignettes of the lives of several residents of a Vienna suburb during a heat wave.
Why it matches: Similar story and style · both drama & 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 drama & comedy
Popcorn FlickMovies like thisPeaceful Times (2008)
After fleeing to the West in 1961, peaceful times were supposed to begin for the Striesows. But Irene longs for the familiar GDR, fears her husband Dieter's supposed "second wives" and expects the Third World War every day. When the war finally breaks out in the living room, her children Ute, Wasa and Flori decide to help their mother's happiness along, with unexpected consequences.
Why it matches: Similar story and style · both comedy & drama
One Deadly Summer (1983)
Shortly after Elle Wieck moves to a small French village, she begins dating Pin-Pon, a quiet young mechanic who has grown obsessed with the beautiful newcomer. But Elle has her own reason for the relationship...
Why it matches: Similar story and style · both drama
Worth the HypeMovies like thisFree!: Take Your Marks (2017)
This film consists of all-new stories that are direct continuations of the previous two films and are told in four episodic parts. The four short stories take place in March as Haruka Nanase is about to graduate from Iwatobi High School.
Why it matches: Similar story and style · both comedy
Green Street Hooligans (2005)
After being wrongfully expelled from Harvard University, American Matt Buckner flees to his sister's home in England. Once there, he is befriended by her charming and dangerous brother-in-law, Pete Dunham, and introduced to the underworld of British football hooliganism. Matt learns to stand his ground through a friendship that develops against the backdrop of this secret and often violent world. 'Green Street Hooligans' is a story of loyalty, trust and the sometimes brutal consequences of living close to the edge.
Why it matches: Similar story and style · both drama
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like Side Out?
The closest matches to Side Out are Why Did I Get Married Again? (2026), My Awkward Sexual Adventure (2012) and Cyrus (2010). Below are 27 more, each with the reason it matches.
What should I watch after Side Out?
Start with Why Did I Get Married Again? (2026), the closest match to Side Out.
What is the highest-rated movie like Side Out?
Love Don't Co$t a Thing (2003), rated 7.7/10 by 741 TMDB users.
What is the newest movie like Side Out?
Why Did I Get Married Again? (2026) is the most recent release on this list.
Are there English movies like Side Out?
Yes: Why Did I Get Married Again? (2026), My Awkward Sexual Adventure (2012) and Cyrus (2010).
How are movies similar to Side Out chosen?
First come films that Trakt’s viewers watch alongside Side Out, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.