Movies like Pretty Boy Josh (2020)
The best movies like Pretty Boy Josh (2020) are Pretty Boy (2015), Bros (2022) and The Half of It (2020). If Pretty Boy Josh hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedMan on the Moon (1999)7.2/10 from 2,085 votes
- NewestDave Chappelle: The Unstoppable... (2025)Released 2025
Pretty Boy (2015)
Sean is taken to a motel and is given a prostitute for his 18th birthday by his father. He must sleep with her to "fix" his questionable homosexuality. "Pretty Boy" is a coming of age story of a young bullied teen, Sean, struggling with his sexuality and the hardships of high school. After his father finds some questionable magazines in his room, this devout Christian will go to any lengths to get his son to find the light and "perform" the way a man should. Sean is introduced to Katie, a prostitute that understands the stigmas of modern society and helps him see the true light that is within him.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisBros (2022)
Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Half of It (2020)
Shy, straight-A student Ellie is hired by sweet but inarticulate jock Paul, who needs help wooing the most popular girl in school. But their new and unlikely friendship gets tricky when Ellie discovers she has feelings for the same girl.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisPillion (2025)
Colin, a timid man, meets Ray, a confident biker gang leader, who initiates him into a submissive relationship, challenging Colin’s mundane existence and prompting personal growth through their unconventional dynamic.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisDave Chappelle: The Unstoppable... (2025)
Facing a world gone sideways, comedy icon Dave Chappelle delivers bold truths and potent punchlines in this no-holds-barred special.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisGiant Little Ones (2019)
Two popular teen boys, best friends since childhood, discover their lives, families, and girlfriends dramatically upended after an unexpected incident occurs on the night of a 17th birthday party.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisThe Art of Getting By (2011)
George, a lonely and fatalistic teen who's made it all the way to his senior year without ever having done a real day of work, is befriended by Sally, a popular but complicated girl who recognizes in him a kindred spirit.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisJust One of the Guys (1985)
When Terry Griffith loses her high school's writing competition, she's convinced that it's because she's a girl. So Terry decides to change high schools and pose as a boy to prove her point. Her brother, Buddy, helps her pass as a guy so well that she is soon making friends with the boys at school, including the attractive Rick, who becomes her new best friend. But her gender-swapping makes things difficult when she falls in love with him.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Girl Next Door (2004)
Exceptionally ambitious high schooler Matthew has aspirations for a career in politics when he falls in love with his gorgeous 19-year-old neighbor, Danielle. But Matthew's bright future is jeopardized when he finds Danielle was once a porn star. As Danielle's past catches up with her, Matthew's love for her forces him to re-evaluate his goals.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisDown with Love (2003)
In 1962 New York City, love blossoms between a playboy journalist and a feminist advice author.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Bachelor and the Bobby-Soxer (1947)
Teenager Susan Turner, with a severe crush on playboy artist Richard Nugent, sneaks into his apartment to model for him and is found there by her sister Judge Margaret Turner. Threatened with jail, Nugent agrees to date Susan until the crush abates.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisArtists and Models (1955)
A struggling painter begins taking inspiration from the dreams of his friend and roommate, a comic book fan who narrates an adventure story while he sleeps, but unbeknownst to the latter, the artist of his favorite comic book lives in the same building as they do with the model for her drawings.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisAlex Strangelove (2018)
Alex Truelove is on a quest to lose his virginity, an event eagerly awaited by his patient girlfriend and cheered on with welcome advice by his rowdy friends. But Alex, a super gregarious dude, is oddly unmotivated. A magical house party throws Alex into the presence of Elliot, a hunky college guy, who pegs Alex as gay and flirts hard. Alex is taken aback but after a series of setbacks on the girlfriend front he takes the plunge and learns some interesting new facts about himself.
Why it matches: Recommended by TMDB viewers
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
Popcorn FlickMovies like thisI Used to Be Funny (2024)
Sam, an aspiring stand-up comedian and au pair struggling with PTSD, weighs whether to join the search for Brooke, a missing teenage girl she used to nanny. As she fights to recover from her trauma and return to the stage, memories of her deep bond with Brooke rush back—making it impossible to ignore her disappearance.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Object of My Affection (1998)
A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisDavid and Lisa (1962)
Teenager David Clemens develops a hysterical fear that he will die if he comes into physical contact with another person. Perturbed, David's overbearing mother places him in a home for mentally disturbed young people, but David remains withdrawn from the other patients and his psychiatrist. Over time, however, David grows interested in 15-year-old Lisa, who suffers from multiple personalities – one who can only speak in rhyme, and the other, a mute.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisMy Brother the Devil (2012)
Fourteen-year-old Mo is a lonely, sensitive boy whose hunger for the rant and banter of buddies makes him prone to tread dangerous territories. He idolizes his handsome older brother, Rashid, a charismatic, well-respected member of a local gang, whose drug dealing enables “Rash” to provide for his family. Aching to be seen as a tough guy himself, Mo takes a job that unlocks a fateful turn of events and forces the brothers to confront their inner demons. It turns out that hate is easy. It is love and understanding that take real courage.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisMan on the Moon (1999)
The story of the life and career of eccentric avant-garde comedian, Andy Kaufman.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisBanana Split (2018)
After a messy breakup with her high school boyfriend, April strikes up an unexpected platonic friendship with his new girlfriend, Clara.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like this
Like Pretty Boy Josh and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Pretty Boy Josh?
The closest matches to Pretty Boy Josh are Pretty Boy (2015), Bros (2022) and The Half of It (2020). Below are 17 more, each with the reason it matches.
What should I watch after Pretty Boy Josh?
Start with Pretty Boy (2015), the closest match to Pretty Boy Josh.
What is the highest-rated movie like Pretty Boy Josh?
Man on the Moon (1999), rated 7.2/10 by 2,085 TMDB users.
What is the newest movie like Pretty Boy Josh?
Dave Chappelle: The Unstoppable... (2025) is the most recent release on this list.
Are there English movies like Pretty Boy Josh?
Yes: Pretty Boy (2015), Bros (2022) and The Half of It (2020).
How are movies similar to Pretty Boy Josh chosen?
First come films that Trakt’s viewers watch alongside Pretty Boy Josh, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.