Movies Like Blackmail Boys

If you liked Blackmail Boys (2010), a drama and comedy movie directed by Joe Swanberg and Adam Wingard, 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
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.
3
The Cable Guy (1996)
★ 6/10Also comedy and drama
When recently single Steven moves into his new apartment, cable guy Chip comes to hook him up—and doesn't let go. Initially, Chip is just overzealous in his desire to be Steven's pal, but when Steven tries to end the…
4
The Parts You Lose (2019)
★ 6.7/10Also drama
An unlikely friendship unfolds between a young deaf boy, Wesley, and a fugitive criminal who takes refuge in an abandoned barn on the family’s rural North Dakota farm.
5
My Own Love Song (2010)
★ 6.2/10Also comedy and drama
A wheelchair-bound singer and her best friend embark on a roadtrip to Memphis.
6
Hostile Takeover (2025)
★ 6.9/10Also comedy
Follows Pete, a professional hitman, as he faces a group of assassins after the boss of a crime syndicate suspects disloyalty due to his attendance at Workaholics Anonymous meetings.
7
The Asphalt Jungle (1950)
★ 7.5/10Also drama
Recently paroled from prison, legendary burglar "Doc" Riedenschneider, with funding from Alonzo Emmerich, a crooked lawyer, gathers a small group of veteran criminals together in the Midwest for a big jewel heist.
8
What Maisie Knew (2013)
★ 7.1/10Also drama
In New York City, six-year-old Maisie is caught in the middle of a bitter custody battle between her self-absorbed parents—an aging rock singer mother and a distracted art dealer father. As both quickly marry new…
9
Buffaloed (2020)
★ 6.6/10Also comedy and drama
Set in the underworld of debt-collecting, homegrown hustler Peg Dahl will do anything to escape Buffalo, NY.
10
Barbershop: The Next Cut (2016)
★ 6.3/10Also comedy and drama
To survive harsh economic times, Calvin and Angie have merged the barbershop and beauty salon into one business. The days of male bonding are gone as Eddie and the crew must now contend with sassy female co-workers and…
11
High Heels and Low Lifes (2001)
★ 6.1/10Also comedy
Two friends are drawn into a seedy underworld of extortion and violence when they try to blackmail a gang of bank robbers.
12
Young Adult (2011)
★ 5.8/10Also comedy and drama
A divorced writer from the Midwest returns to her hometown to reconnect with an old flame, who's now married with a family.
13
Heist (2001)
★ 6.3/10Also drama
Joe Moore has a job he loves. He's a thief. His job goes sour when he gets caught on security camera tape. His fence, Bergman, reneges on the money he's owed, and his wife may be betraying him with the fence's young…
14
Fast Girls (2012)
★ 6/10Also drama
A street smart runner develops an intense rivalry with an equally ambitious wealthy young athlete.
15
Savage House (2026)
★ 7/10Also comedy and drama
Against the backdrop of 18th century England, a massive pox outbreak, and Jacobite uprising – Sir Chauncey Savage and Lady Savage blindly pursue a better life. It's not without a tinge of irony that their family name…
16
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.
17
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…
18
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…
19
The River (1984)
★ 6.4/10Also drama
Tom and Mae Garvey are a Tennessee farming couple battling violent floods to save their land. In addition to natural disasters, the Garveys fight to stop a selfish land developer and a local corporation from…
20
How to Rob a Bank (2007)
★ 5.8/10Also comedy
Caught in the middle of a bank robbery, a slacker and a bank employee become the ones who arbitrate the intense situation.