Movies Like Bossman

If you liked Bossman, a comedy and crime movie directed by Jacob Thompson, 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
Thick as Thieves (1999)
★ 6/10Also drama and comedy
Two master thieves go at odds with one another as one sets the other up for a crime. The first, a suave pro who does his job and then hides in his own privacy, listening to old jazz records and caring for his ailing…
2
Breaking News in Yuba County (2021)
★ 5.9/10Also comedy and drama
An overlooked pencil-pusher catches her husband in bed with another woman, the shock of which causes him to die of a heart attack. So she buries his body and takes advantage of the growing celebrity status that comes…
3
Where the Money Is (2000)
★ 5.9/10Also comedy and crime
Henry Manning has come up with a new way to break out of prison: fake a stroke and get transferred to a nursing home. It's a perfect plan, except for one thing: the woman assigned to take care of him at the nursing…
4
Small Apartments (2012)
★ 5.9/10Also comedy and crime
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…
5
Intermission (2003)
★ 6.2/10Also comedy and crime
A raucous story of the interweaving lives and loves of small-town delinquents, shady cops, pretty good girls and very bad boys. With Irish guts and grit, lives collide, preconceptions shatter and romance is tested to…
6
Blindspotting (2018)
★ 7.3/10Also comedy and crime
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…
7
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy and crime
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
8
Thin Ice (2012)
★ 6.5/10Also comedy and crime
A dishonest insurance salesman's life quickly disintegrates during a Wisconsin winter when he teams up with a psychopath to steal a rare violin at the home of a reclusive farmer.
9
Simpsley (2026)
★ 8.1/10Also comedy and crime
When penniless con-artist Marge Bouvier is sent to Italy to convince wealthy sap Seymour Skinner to come home, she's tempted by the trappings of his affluent lifestyle. But there’s a big fat fly in the ointment…
10
Panic (2000)
★ 6.2/10Also crime and drama
Alex is going through a midlife crisis and it has become a very difficult time for him. His marriage is struggling, he's worried about his son, and his job of killing people for his family has become the most stressful…
11
The Parts You Lose (2019)
★ 6.7/10Also drama and crime
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.
12
Defendor (2009)
★ 6.4/10Also drama and comedy
A crooked cop, a mob boss and the young girl they abuse are the denizens of a city's criminal underworld. It's a world that ordinary Arthur Poppington doesn't understand and doesn't belong in, but is committed to…
13
How to Rob a Bank (2007)
★ 5.8/10Also comedy and crime
Caught in the middle of a bank robbery, a slacker and a bank employee become the ones who arbitrate the intense situation.
14
Things Change (1988)
★ 6.2/10Also comedy and crime
Jerry, a misfit Mafia henchman, is assigned the low-level job of keeping an eye on Gino, a shoe repairman fingered by the Mob to confess to a murder he didn't commit. But Gino's mistaken for a Mafia boss, and the two…
15
Cigarettes & Coffee (1993)
★ 6.6/10Also drama and crime
At a desert diner, the lives of five strangers become linked through a single twenty-dollar bill. Shot for $20,000 and starring Philip Baker Hall, the short premiered at Sundance and later inspired Anderson’s debut…
16
Accident Man (2018)
★ 6.3/10Also crime and comedy
Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.
17
Plunder Road (1957)
★ 6.9/10Also crime and drama
A spectacular heist starts to unravel as the crooks take it on the lam.
18
Suburbicon (2017)
★ 5.9/10Also crime and drama
In the quiet family town of Suburbicon during the 1950s, the best and worst of humanity is hilariously reflected through the deeds of seemingly ordinary people. When a home invasion turns deadly, a picture-perfect…
19
Bottle Rocket (1996)
★ 6.7/10Also comedy and crime
Upon his release from a mental hospital following a nervous breakdown, the directionless Anthony joins his friend Dignan, who seems far less sane than the former. Dignan has hatched a harebrained scheme for an…
20
Amateur (1994)
★ 6.2/10Also crime and comedy
A man wakes up in an alley, bleeding and with no memory of who he is. He stumbles into a coffee shop and is befriended by a charitable ex-nun who is failing in her attempts to write marketable pornography.