Movies Like Boys on the Side
If you loved Boys on the Side's Comedy and Drama storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks

Will & Harper
When Will Ferrell's good friend Harper comes out as a trans woman, they take a road trip to bond and reintroduce Harper to the country as her true self.

Ana
Ana meets Rafa in a chance encounter and they embark on a road trip to try and save him from bankruptcy, or worse.

Burn Burn Burn
Following the death of their friend, two girls in their late twenties embark on a road trip to spread his ashes. Seph and Alex take turns driving. Dan is in the glove compartment, in tupperware, decreasing in volume as the trip progresses.

Reality Bites
A small circle of friends suffering from post-collegiate blues must confront the hard truth about life, love and the pursuit of gainful employment. As they struggle to map out survival guides for the future, the Gen-X quartet soon begins to realize that reality isn't all it's cracked up to be.

Unpregnant
After discovering she can’t legally get an abortion in Missouri without her parents’ permission, teenager Veronica convinces her former best friend Bailey to take a road trip to Albuquerque to seek the procedure.

As Good as It Gets
A misanthropic author, a single mother and waitress, and a gay artist form an unlikely friendship after the artist is assaulted in a robbery.

Poetic Justice
Still grieving after the murder of her boyfriend, hairdresser Justice writes poetry to deal with the pain of her loss. Unable to get to Oakland to attend a convention because of her broken-down car, Justice gets a lift with her friend, Iesha, and Iesha's postal worker boyfriend, Chicago. Along for the ride is Chicago's co-worker, Lucky, to whom Justice grows close after some initial problems. But is she ready to open her heart again?
More Movies Like Boys on the Side

Ezra
Stand-up comedian Max Bernal lives with his father Stan while struggling to co-parent his autistic son Ezra with his ex-wife. When forced to confront difficult decisions about their son's future, Max and Ezra embark on a cross-country road trip that has a transcendent impact on both their lives.

Girlfriends
A photographer and her best friend are roommates. She is stuck with small-change shooting jobs and dreams of success. When her roommate decides to get married and leave, she feels hurt and has to learn how to deal with living alone.

Grandma
Self-described misanthrope Elle Reid has her protective bubble burst when her 18-year-old granddaughter, Sage, shows up needing help. The two of them go on a day-long journey that causes Elle to come to terms with her past and Sage to confront her future.

Jeffrey
Jeffrey, a gay man living in New York City with an overwhelming fear of contracting AIDS, concludes that being celibate is the only option to protect himself. As fate would have it, shortly after his declaration of a sex-free existence, he meets the handsome Steve Howard, his dream man -- except for his HIV-positive status. Facing this dilemma, Jeffrey turns to his best friend and an outrageous priest for guidance.

All About Sex
Three friends in their mid-20s struggle to navigate their professional and personal lives, colliding head on with the messy, hilarious and dreadful growing pangs of adulthood.

Palmer
After 12 years in prison, former high school football star Eddie Palmer returns home to put his life back together—and forms an unlikely bond with Sam, an outcast boy from a troubled home. But Eddie's past threatens to ruin his new life and family.

The Daytrippers
Eliza D'Amico thinks her marriage to Louis is going great until she finds a mysterious love note to her husband. Concerned, she goes to her mother for advice. Eliza, her parents, her sister Jo, and Jo's boyfriend all pile into the station wagon and go to the city to confront Louis with the letter. On the way, the five explore their relations with each other and meet many interesting people.

XX/XY
Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.

My Girl
Vada Sultenfuss is obsessed with death. Her mother is dead, and her father runs a funeral parlor. She is also in love with her English teacher, and joins a poetry class over the summer just to impress him. Thomas J., her best friend, is "allergic to everything", and sticks with Vada despite her hangups. When Vada's father hires Shelly, and begins to fall for her, things take a turn to the worse...

The Bucket List
Corporate billionaire Edward Cole and working class mechanic Carter Chambers are worlds apart. At a crossroads in their lives, they share a hospital room and discover they have two things in common: a desire to spend the time they have left doing everything they ever wanted to do and an unrealized need to come to terms with who they are. Together they embark on the road trip of a lifetime, becoming friends along the way and learning to live life to the fullest, with insight and humor.

Green Book
Tony Lip, a bouncer in 1962, is hired to drive pianist Don Shirley on a tour through the Deep South in the days when African Americans, forced to find alternate accommodations and services due to segregation laws below the Mason-Dixon Line, relied on a guide called The Negro Motorist Green Book.

Thelma & Louise
Taking a break from their dreary lives, close friends Thelma and Louise embark on a short weekend trip that ends in unforeseen incriminating circumstances. As fugitives, both women rediscover the strength of their bond and their newfound resilience.
Why These Movies Are Similar
These recommendations share core qualities with Boys on the Side (1995): Comedy and Drama themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Boys on the Side.
See full details for Boys on the Side (1995)
