Movies Like Outsize Pursuits

If you liked Outsize Pursuits (2004), a movie directed by Clive Roberts, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Everything You Always Wanted to Know About Sex *But Were Afraid to Ask (1972)
★ 6.5/10
A collection of seven vignettes, which each address a question concerning human sexuality. From aphrodisiacs to sexual perversion to the mystery of the male orgasm, characters like a court jester, a doctor, a queen and…
2
Porno (2019)
★ 6/10
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.
3
Barely Legal (2003)
★ 5.9/10
Teenager Deacon works at a video shop, and his buddies, Fred and Matt, sell the bootleg porno films he acquires. Deacon gets fired, but the pals have the bright idea of filming their own Internet porn flick in order to…
4
Alex Strangelove (2018)
★ 6.6/10
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…
5
Jackass: Best and Last (2026)
★ 7.3/10
The fifth and final installment to Jackass franchise where the crew go on one last insane crusade.
6
Fear Below (2025)
★ 6.1/10
A rag-tag team of divers attempting to salvage a sunken car from a river are thwarted by a highly aggressive bull shark.
7
Magazine Dreams (2025)
★ 7/10
Aspiring bodybuilder Killian Maddox struggles to find human connection in an exploration of celebrity and violence. Nothing deters him from his fiercely protected dream of superstardom, not even the doctors who warn…
8
Dinner in America (2022)
★ 7.8/10
An on-the-lam punk rocker and a young woman obsessed with a local band go on an unexpected and epic journey together through the decaying suburbs of the American Midwest.
9
The Wonderful Story of Henry Sugar and Three More (2024)
★ 7.4/10
Four tales unfold in Wes Anderson's anthology of short films adapted from Roald Dahl's beloved stories, "The Wonderful Story of Henry Sugar", "The Swan", "The Rat Catcher", and "Poison."
10
Pillion (2025)
★ 6.5/10
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.
11
My Awkward Sexual Adventure (2012)
★ 6.7/10
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.
12
Orgazmo (1998)
★ 6.1/10
A devout Mormon living in L.A. becomes a pornographic actor after his martial arts moves impress a big-time director.
13
American Wedding (2003)
★ 6.2/10
With high school a distant memory, Jim and Michelle are getting married — and in a hurry, since Jim's grandmother is sick and wants to see him walk down the aisle — prompting Stifler to throw the ultimate bachelor…
14
Send Me No Flowers (1964)
★ 6.8/10
When a hypochondriac assumes that he is dying, he makes an elaborate plan to ensure his wife's happiness. However, trouble ensues when she misunderstands his intentions.
15
WWE WrestleMania XXX (2014)
★ 7.9/10
WrestleMania XXX was the 30th annual WrestleMania professional wrestling PPV event produced by WWE to be held, on April 6, 2014, at the Mercedes-Benz Superdome in New Orleans, Louisiana. The event was the first…
16
Young People Fucking (2007)
★ 5.9/10
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…
17
Watching the Detectives (2007)
★ 6.3/10
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…
18
Tuff Turf (1985)
★ 5.9/10
The new guy in a Los Angeles high school, Morgan, does some singing and fights hotshot Nick over disco dancer Frankie.
19
Trojan War (1997)
★ 6/10
Brad is about to hook up with the girl of his dreams, but runs into a problem, no condom. So Brad sets out into the night to find one, running into many obstacles along the way, while not knowing his best friend, Leah…
20
Road Trip (2000)
★ 6.3/10
After a student at the University of Ithaca films his one-night stand with a beautiful sorority girl, he discovers one of his friends has accidentally mailed the homemade sex tape to his girlfriend in Austin. In a…