Most Similar Movies to Cadillac Man (1990)
If you are looking for movies like Cadillac Man (1990), you might like movies tagged with keyword : comedy, crime, robin williams, dark comedy, 1980s, new york, workplace, midlife crisis, deception, money, pressure, redemption, absurd, fast-paced, ensemble cast, satire, male protagonist, survival, chaos, tension .
A Very Honorable Guy (1934), Go (1999), The Squeeze (1987), Short Time (1990), Free Fire (2016), The Freshman (1990), The Last Time (2006) ... Let's take a look at the following list...

A Very Honorable Guy (1934)
Well respected local good guy, Feet Samuels finds himself heavily in debt due to an uncharacteristic gambling binge. Feet decides the only way to settle the bill is by selling his body to an ambitious doctor who agrees to allow him one last month to live life to the fullest, then kill himself.
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Go (1999)
A checkout girl covering for a co-worker (Desmond Askew) faces danger from a drug dealer she double-crosses out of desperation.
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The Squeeze (1987)
A mysterious black box spells danger to a con man and female detective.
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Short Time (1990)
When a police detective thinks he is dying and learns that his life insurance pays out more if he dies in the line of duty, he tries to make that happen.
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Free Fire (2016)
Set in Boston in 1978, a meeting in a deserted warehouse between two gangs turns into a shoot-out and a game of survival.
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The Freshman (1990)
An N.Y.C. film school student accepts a job with a local mobster who resembles a famous cinema godfather and who takes the young man under his wing, after demanding total loyalty.
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The Last Time (2006)
A salesman (Keaton) rediscovers a lust for life after falling for the fiancée of his new business partner (Fraser), a Midwest transplant finding his footing in New York City.
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30 Minutes or Less (2011)
Two fledgling criminals kidnap a pizza delivery guy, strap a bomb to his chest, and inform him that he has mere hours to rob a bank or else...
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The Survivors (1983)
Having both lost their jobs, two strangers become unlikely friends after a run in with a would be robber, who is actually a hitman with a grudge against the two.
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A Bad Idea Gone Wrong (2017)
Two would-be thieves forge a surprising relationship with an unexpected house-sitter when they accidentally trap themselves in a house they just broke into.
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Family Business (1989)
An ex professor offers Adam $1,000,000 to "get" some plasma from a high tech company's lab. Adam asks his criminal grandpa for help. Can the 2 convince Adam's now honest dad to join?Let us see what happens.
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Big Trouble (2002)
A mysterious suitcase brings together a single father (Tim Allen), an unhappy housewife (Rene Russo), hit men, street thugs and the FBI.
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Diamond Men (2000)
A jewelry salesman (Robert Forster) trains his replacement (Donnie Wahlberg) by taking him on the road in Philadelphia.
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Delhi Belly (2011)
Three struggling room-mates unknowingly become potential prey of a ruthless gangster.
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The Honey Pot (1967)
In Venice, a millionaire hires an actor to help him prank three greedy ex-girlfriends into thinking he's dying and leaving his fortune to one of them.
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Ruthless People (1986)
A couple, cheated by a vile businessman, kidnap his wife in retaliation, without knowing that their enemy is delighted they did.
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Big Trouble (2002)
The lives of several Miami denizens, from ad agents to gunrunners to street thugs to law enforcement to school-children, intersect with humorous and dangerous results.
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Stretch (2014)
A hard-luck limo driver struggles to go straight and pay off a debt to his bookie. He takes on a job with a crazed passenger, whose sought-after ledger implicates some seriously dangerous criminals.
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