Movies Like Milwaukee, Minnesota

If you liked Milwaukee, Minnesota (2003), a comedy and drama movie directed by Allan Mindel, 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
Six Degrees of Separation (1993)
★ 6.4/10Also drama and comedy
The story of a young, gay, black, con artist who, posing as the son of Sidney Poitier, cunningly maneuvers his way into the lives of a white, upper-class New York family.
2
Criminal (2004)
★ 6.2/10Also comedy
Needing a new partner capable of intricate cons, Richard Gaddis, recruits Rodrigo, a crook with a perfect poker face. The two plan a big-time scam: selling a fake Silver Certificate to currency collector William…
3
Ca$h (2010)
★ 5.9/10Also comedy
A stroke of good luck turns lethal for Sam Phelan and his wife Leslie when they are faced with a life-changing decision that brings strange and sinister Pyke Kubic to their doorstep. As Pyke leads Sam and Leslie on a…
4
House of Games (1987)
★ 6.8/10Also drama
A psychiatrist comes to the aid of a compulsive gambler and is led by a smooth-talking grifter into the shadowy but compelling world of stings, scams, and con men.
5
CQ (2001)
★ 5.9/10Also comedy and drama
A young filmmaker in 1960s Paris juggles directing a cheesy sci-fi debacle, directing his own personal art film, coping with his crumbling relationship with his girlfriend, and a new-found infatuation with the sci-fi…
6
Pacific Heights (1990)
★ 6.3/10Also drama
A couple works hard to renovate their dream house and become landlords to pay for it. Unfortunately one of their tenants has plans of his own.
7
Thin Ice (2012)
★ 6.5/10Also comedy and drama
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.
8
Playing God (2021)
★ 6/10Also comedy and drama
A brother and sister con-artist duo find themselves scamming a grieving billionaire by convincing him they can introduce him to God, face-to-face.
9
Panic (2000)
★ 6.2/10Also 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…
10
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.
11
The Killer's Game (2024)
★ 6.4/10Also comedy
When top hitman Joe Flood is diagnosed with a terminal illness, he decides to take matters into his own hands – by taking a hit out on himself. But when the very hitmen he hired also target his ex-girlfriend, he must…
12
Almost Friends (2017)
★ 6.3/10Also drama and comedy
A man in his mid-20s, still living at home with his mother and stepfather, puts all his eggs in one basket: the girl who works at his local coffee shop. The problem is, she has a serious boyfriend. As they become…
13
A Perfect Murder (1998)
★ 6.6/10Also drama
Millionaire industrialist Steven Taylor is a man who has everything but what he craves most: the love and fidelity of his wife. A hugely successful player in the New York financial world, he considers her to be his…
14
American Hustle (2013)
★ 6.9/10Also drama
A conman and his seductive partner are forced to work for a wild FBI agent, who pushes them into a world of Jersey power-brokers and the Mafia.
15
Bottle Rocket (1996)
★ 6.7/10Also comedy and drama
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…
16
Box of Moonlight (1996)
★ 6.8/10Also comedy and drama
Al Fountain, a middle-aged electrical engineer, is on the verge of a mid-life crisis, when he decides to take his time coming home from a business trip, rents a car, and heads out looking for a lake he remembers from…
17
The Whole Nine Yards (2000)
★ 6.5/10Also comedy
After a mobster agrees to cooperate with an FBI investigation in order to stay out of prison, he's relocated by the authorities to a life of suburban anonymity as part of a witness protection program. It's not long…
18
Easy Money (1983)
★ 6/10Also comedy
To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.
19
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…
20
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…