Movies like In Deep: Miles to Go (1999)
The best movies like In Deep: Miles to Go (1999) are The Bachelor and the Bobby-Soxer (1947), My Fake Boyfriend (2022) and Porno (2019). If In Deep: Miles to Go hooked you, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedBlindspotting (2018)7.3/10 from 757 votes
- NewestStraight Guy Watches Gay Porn for the First Time (2026)Released 2026
The 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 thisMy Fake Boyfriend (2022)
A young man in a tricky situation follows the advice of his unconventional best friend and uses social media to create a fake boyfriend to keep his awful ex-lover out of his life. But everything backfires when he meets the real love of his life, and breaking up with his fake boyfriend proves hard to do.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisPorno (2019)
When a group of naive teens working at a movie theater in a small Christian town discover a mysterious film hidden in its basement, they unleash an alluring succubus who gives them a sex education…written in blood.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisLife (2015)
In 1955, young photographer Dennis Stock develops a close bond with actor James Dean while shooting pictures of the rising Hollywood star.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisScorpio Rising (1964)
A gang of bikers prepares for a race as sexual, sadistic, and occult images are cut together.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisKing Cobra (2016)
It’s 2006, YouTube is in its infancy, and internet porn is still behind a paywall. Taking the stage name Brent Corrigan, a fresh-faced, wannabe adult video performer is molded into a star by Stephen, a closeted gay porn mogul who runs the skin flick empire Cobra Video from his seemingly ordinary suburban home.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisIn the Blood (2014)
When her husband goes missing during their Caribbean vacation, a woman sets off on her own to take down the men she thinks are responsible.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisYour Friends & Neighbors (1998)
Restless and unhappy, two couples get caught up in infidelity and deception. Barry is a sullen businessman married to Mary, a writer who is unsatisfied with their relationship. Mary begins an affair with Jerry, a smug theater professor and husband of her friend, Terri, who is also a writer. Adding to the adulterous mix are Cary, a callous doctor, and Cheri, an art-gallery assistant.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisBlindspotting (2018)
Collin must make it through his final three days of probation for a chance at a new beginning. He and his troublemaking childhood best friend, Miles, work as movers, and when Collin witnesses a police shooting, the two men’s friendship is tested as they grapple with identity and their changed realities in the rapidly-gentrifying neighborhood they grew up in.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisA Month in the Country (1987)
A destitute WWI veteran is hired to help carry out restoration work on a medieval mural in a rural Yorkshire church. While living in the quiet village, he forms a close friendship with an archaeologist and begins to come to terms with his trauma.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSmall Apartments (2012)
When a clumsy deadbeat accidentally kills his landlord, he must do everything in his power to hide the body, only to find that the distractions of lust, the death of his beloved brother, and a crew of misfit characters force him on a journey where a fortune awaits him.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisSalting the Battlefield (2014)
David Hare concludes his trilogy of films about MI5 renegade Johnny Worricker with another fugue on power, secrets and the British establishment. Johnny Worricker goes on the run with Margot Tyrell across Europe, and with the net closing in, the former MI5 man knows his only chance of resolving his problems is to return home and confront prime minister Alec Beasley.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisLemmy (2010)
Over four decades, Motorhead frontman Lemmy Kilmister has registered an immeasurable impact on music history. Nearly 65, he remains the living embodiment of the rock and roll lifestyle, and this feature-length documentary tells his story, one of a hard-living rock icon who continues to enjoy the life of a man half his age.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisChristmas Next Door (2017)
Eric Randall, an author of bachelor lifestyle books, is left in charge of his young niece and nephew for the holidays. Eric turns to his neighbor April, a lover of all things Christmas, for help.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisNaked as We Came (2013)
After an unexpected phone call, Laura and her brother Elliot rush to their family’s country estate to find their mother, Lilly, gravely ill and living with a handsome young stranger named Ted. Estranged for some time, their mother’s condition sets Laura and Elliot on a path to realizing where their own lives have gone wrong.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisWelcome to Chechnya (2020)
This searing investigative work shadows a group of activists risking unimaginable peril to confront the ongoing anti-LGBTQ program raging in the repressive and closed Russian republic. Unfettered access and a remarkable approach to protecting anonymity exposes this under-reported atrocity–and an extraordinary group of people confronting evil.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisMass Effect: Paragon Lost (2012)
An untold chapter in the Mass Effect saga, following the early career of Alliance Marine, James Vega, as he leads a squad of elite special forces into battle against a mysterious alien threat known as The Collectors. Stationed at a colony in a remote star system, Vega and his troops must protect the inhabitants from an invasion of the deadly insectoid warriors determined to collect the population for unknown purposes. Soon after the attack, Vega's commanding officer falls in battle, forcing the young officer to embrace the responsibility of leadership for the colony's survival. Having idolized Earth's greatest hero and warrior, Commander Shepard (the central character in the Mass Effect video games), the young and idealistic Vega must now make life and the death decisions that will effect not only the lives of his squad, but the lives of every person in the colony - all of whom he has sworn to protect...
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisNaughty or Nice (2012)
Krissy Kringle receives a delivery intended for Santa Claus. A magical book that shows if a person has been naughty or nice. She uses the book's power to find out about those around her, which leads to some very unusual and unintended results. Krissy realizes that everyone has some good and some not so good in them.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Paper Tigers (2020)
Three middle aged men polish their martial arts skills to avenge their fallen master.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisDeuce Bigalow: Male Gigolo (1999)
Deuce Bigalow is a less than attractive, down on his luck aquarium cleaner. One day he wrecks the house of a gigolo and needs quick money to repair it. The only way he can make it is to become a gigolo himself, taking on an unusual mix of female clients. He encounters a couple of problems, though. He falls in love with one of his unusual clients, and a sleazy police officer is hot on his trail.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisTitle 18 (2022)
An experimental short film made as part of a multi-media triptych, originally screened alongside a fashion collection and an art-installation. Drawing from Papa Yorick’s (Director and fashion designer) thesis “Men Are My Cumrag”, the film reenacts eight mainstay gay porn scripts, incorporating and parodying tropes and clichés, that explore masculine identities within the gay porn industry, through a satirical and critical lens.
Why it matches: Similar story and style
Tips (2016)
Mario (Thiago Cazado) is in debt. To pay the bills, he displays the body on a famous porn site.
Why it matches: Similar story and style
The Fall of Communism as Seen in Gay Pornography (1998)
Every image in The Fall of Communism as Seen in Gay Pornography comes from gay erotic videos produced in Eastern Europe since the introduction of capitalism. The video provides a glimpse of young men responding to the pressures of an unfamiliar world, one in which money, power and sex are now connected.
Why it matches: Similar story and style
Straight Guy Watches Gay Porn for the First Time (2026)
When Janek, a straight Polish guy watches gay porn for the first time, his world is turned upside down. Battling with unsettling new thoughts, he is put into a journey of self-discovery.
Why it matches: Similar story and style
The Fluffer (2001)
Self-effacing, boyish Sean moves to LA to pursue a career in movies but finds it tougher than he imagined. He stumbles onto porn star Johnny Rebel - a handsome, muscled dream of men and women alike - who awakens Sean’s deep obsession.
Why it matches: Similar story and style
SnoozefestMovies like thisI'm a Porn Star (2013)
I'm a Porn Star follows the lives of guys in the neighborhood who are likely a lot more famous than you - at least on the Internet. There are an estimated 370 million pornographic websites on-line. Porn is now a thirteen BILLION dollar business. So who's doing all this moonlighting? Turns out -- probably some people you know.
Why it matches: Similar story and style
Without a Mom (2011)
Two gay dads fumble to provide their straight son with meaningful support after the loss of his first real love.
Why it matches: Similar story and style
Knife+Heart (2018)
In the summer of 1979, gay porn producer Anne sets out to film her most ambitious film yet, but her actors are picked off, one by one, by a mysterious killer.
Why it matches: Similar story and style
SnoozefestMovies like thisThe Day I've Been Fucked in Front of the Entire World (2023)
Remodeling of a pornographic scene in which I shot for a major French studio. It was a question of reappropriating these images (originally categorized as "hard") to extract their erotic and perhaps even romantic potential.
Why it matches: Similar story and style
The Inner Shadow (2018)
Son of a patriarchal family in the country interior finds out something.
Why it matches: Similar story and style
Like In Deep: Miles to Go and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like In Deep: Miles to Go?
The closest matches to In Deep: Miles to Go are The Bachelor and the Bobby-Soxer (1947), My Fake Boyfriend (2022) and Porno (2019). Below are 27 more, each with the reason it matches.
What should I watch after In Deep: Miles to Go?
Start with The Bachelor and the Bobby-Soxer (1947), the closest match to In Deep: Miles to Go.
What is the highest-rated movie like In Deep: Miles to Go?
Blindspotting (2018), rated 7.3/10 by 757 TMDB users.
What is the newest movie like In Deep: Miles to Go?
Straight Guy Watches Gay Porn for the First Time (2026) is the most recent release on this list.
Are there English movies like In Deep: Miles to Go?
Yes: The Bachelor and the Bobby-Soxer (1947), My Fake Boyfriend (2022) and Porno (2019).
How are movies similar to In Deep: Miles to Go chosen?
First come films that Trakt’s viewers watch alongside In Deep: Miles to Go, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.