Movies Like The Pool Boys

If you liked The Pool Boys (2009), a comedy and drama movie directed by J.B. Rogers, 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
The King of Comedy (1982)
★ 7.8/10Also drama and comedy
Aspiring comic Rupert Pupkin attempts to achieve success in show business by stalking his idol, a late night talk-show host who craves his own privacy.
2
City Island (2009)
★ 6.9/10Also drama and comedy
The Rizzos, a family who doesn't share their habits, aspirations, and careers with one another, find their delicate web of lies disturbed by the arrival of a young ex-con brought home by Vince, the patriarch of the…
3
Fletch (1985)
★ 6.7/10Also comedy
When investigative reporter Irwin "Fletch" Fletcher goes undercover to write a piece on the drug trade at a local beach, he's approached by wealthy businessman Alan Stanwyk, who offers him $50,000 to murder him. With…
4
The Dink (2026)
★ 6.4/10Also comedy
Desperate to save a struggling country club and earn his father's respect, a washed-up tennis pro is compelled to break a sacred vow and do the unthinkable: play pickleball.
5
The Distinguished Gentleman (1992)
★ 6/10Also comedy
A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows…
6
SubUrbia (1997)
★ 6.2/10Also comedy and drama
A group of suburban teenagers try to support each other through the difficult task of becoming adults.
7
Oscar (1991)
★ 6.4/10Also comedy
Angelo "Snaps" Provolone made his dying father a promise on his deathbed: he would leave the world of crime and become an honest businessman. Despite having no experience in making money in a legal fashion, Snaps sets…
8
Weekend at Bernie's (1989)
★ 6.4/10Also comedy
Two young insurance corporation employees try to pretend that their murdered employer is alive by puppeteering his dead body, leading a hitman to attempt to track him down to finish him off.
9
Man on the Moon (1999)
★ 7.2/10Also comedy and drama
The story of the life and career of eccentric avant-garde comedian, Andy Kaufman.
10
Welcome to Collinwood (2002)
★ 6.1/10Also comedy
Five hapless inner-city low-lifes attempt to burgle a pawnbroker's safe, but end up being plagued by bad luck.
11
Date Night (2010)
★ 6.1/10Also comedy
Phil and Claire Foster fear that their mild-mannered relationship may be falling into a stale rut. During their weekly date night, their dinner reservation leads to their being mistaken for a couple of thieves—and now…
12
Catch Me If You Can (2002)
★ 8/10Also drama
A true story about Frank Abagnale Jr. who, before his 19th birthday, successfully conned millions of dollars worth of checks as a Pan Am pilot, doctor, and legal prosecutor. An FBI agent makes it his mission to put him…
13
Big Momma's House (2000)
★ 5.8/10Also comedy
When a street-smart FBI agent is sent to Georgia to protect a beautiful single mother and her son from an escaped convict, he is forced to impersonate a crass Southern granny known as Big Momma in order to remain…
14
Power (1986)
★ 5.8/10Also drama
Pete St. John is a powerful and successful political consultant, with clients spread around the country. When his long-time friend and client Ohio senator Sam Hastings decides to quit politics, he is rapidly drafted to…
15
Don't Think Twice (2016)
★ 6.4/10Also comedy and drama
An improv group deals with several crises, including the loss of their lease and one member hitting the big time.
16
Horrible Bosses 2 (2014)
★ 6.2/10Also comedy
Dale, Kurt and Nick decide to start their own business but things don't go as planned because of a slick investor, prompting the trio to pull off a harebrained and misguided kidnapping scheme.
17
Woman of Straw (1964)
★ 6.2/10Also drama
Anthony Richmond schemes to get the fortune of his tyrannical, wheelchair-using tycoon uncle Charles Richmond by persuading Maria, a nurse he employs, to marry him.
18
White Men Can't Jump (1992)
★ 6.7/10Also comedy and drama
Two street basketball hustlers try to con each other, then team up for a bigger score.
19
The Cheyenne Social Club (1970)
★ 6.4/10Also comedy
Cowboy John O'Hanlan is surprised to learn that someone's left him a business in Cheyenne, Wyoming. He sets out to claim it, only to discover it's a brothel.
20
Code 3 (2025)
★ 7.1/10Also comedy and drama
A burned-out paramedic tries to survive his last 24 hours on the job while training a new recruit.