Movies like The Highwayman

If you like "The Highwayman" you are looking for clever, humorous and realistic movies about / with heist, psychopath, dark humor, crimes, on the road, parents and children and vengeance themes of Comedy, Drama and Thriller genre shot in USA or Canada.
Find your next favorite and similar movies in two steps: 1. Identify all themes of interest from this film (block below). 2. Look for them in the presented list.
The Highwayman (2000)
 4.4
 358
The Highwayman (2000)
Genre: Comedy, Drama, Thriller
Country: USA, Canada
Duration: 94 min.
Story: A dark, comedic thriller about fraud, bank robbers and a search for love.
Style: clever, humorous, realistic, suspenseful, cynical, semi serious, road movie
Plot: heist, psychopath, dark humor, crimes, on the road, parents and children, vengeance, store, on the run, nothing goes right, disorder, estrangement, dishonesty, criminal heroes, cons and scams, bank robber, surrealism, suicide attempt, landlady, eviction, long lost daughter, shotgun, crime
Time: 90s

Movie in categories

heist movies
2148
psychopath movies
3779
dark humor movies
3256
90s movies
90s
6439
clever movies
6630
humorous movies
19364
crimes movies
14741

Most similar movies to The Highwayman

The list contains related movies ordered by similarity. Recommendation engine sorted out realistic, humorous, semi serious and cynical films with plots about crimes, disorder, dishonesty, cons and scams, crime gone awry, criminal heroes and dark humor mostly in Comedy, Drama and Thriller genres. Some movies like The Highwayman: Out Cold (1989), Trouble Bound (1993), Homegrown (1998), Scarfies (1999), Cold Feet (1989). The matching attributes are highlighted in bold.
 5.4
 804
Out Cold (1989)
Genre: Comedy, Drama, Thriller
Country: USA
Duration: 92 min.
Story: A comedy about an angry married couple, a private investigator, and a walk-in freezer.
Style: cynical, semi serious, realistic, humorous, suspenseful ...
Plot: infidelity, private detective, frame up, murder, disorder, couples, dark humor, partners, dishonesty, nothing goes right, crimes, law enforcement ...
Time: 80s
⇓ similarity ⇓
95%
 5.5
 933
Trouble Bound (1993)
Genre: Action, Comedy, Crime, Drama, Thriller
Country: USA, UK
Duration: 90 min.
Story: Upon getting out of prison, a man who took the rap for some thief buddies gets together with them again, and tells them he's not interested in doing things with them any more. They stick a dead body in his trunk, unbeknownst to him, and he ...
Style: realistic, suspenseful, cynical, serious, humorous ...
Audience: boys' night
Plot: mafia, gangsters, unlikely partners, criminal heroes, hitman, disorder, obsessive quest, nothing goes right, crime gone awry, criminal's revenge, crimes, on the road ...
Time: 90s
Place: nevada
⇓ similarity ⇓
81%
 5.7
 5K
Homegrown (1998)
Genre: Comedy, Crime, Drama, Thriller
Country: USA
Duration: 102 min.
Story: Three laborers on a Northern California marijuana plantation become increasingly paranoid when they learn that their boss has been murdered. They know enough to run, taking with them enough of the crop to pay them for services rendered. Hooking up ...
Style: suspenseful, realistic, semi serious, humorous, stylized ...
Audience: boys' night
Plot: drug dealing, drug abuse, crimes, dishonesty, disorder, buddies, nothing goes right, criminal heroes, partners, murder, greed, gunfight ...
Time: 90s
Place: california, usa
⇓ similarity ⇓
76%
 6.4
 1K
Scarfies (1999)
Genre: Action, Comedy, Thriller
Country: New Zealand
Duration: 94 min.
Story: This dark comedy is set in Dunedin, New Zealand. A university student finds an old "abandoned" house and proceeds to invite other students to share. It even has running electricity. But what is the catch?
Style: cynical, semi serious, realistic, humorous, suspenseful ...
Plot: disorder, unlikely criminals, crime gone awry, nothing goes right, drug dealing, youth, crimes, criminal heroes, cons and scams, college, abandoned, gang ...
Time: 90s
Place: new zealand
⇓ similarity ⇓
73%
Movie in collections
 4.7
 415
Cold Feet (1989)
Genre: Comedy, Crime
Country: USA
Duration: 94 min.
Story: The leader of a group of misfits, his girlfriend and an assassin have devised a bizarre plan to smuggle stolen jewelry over the US/Mexican border. They implant the jewelry in a racing horse.
Style: semi serious, realistic, cynical, humorous, witty ...
Plot: cons and scams, down on your luck, partners, on the run, dishonesty, crimes, criminal heroes, nothing goes right, disorder, hitman, psychopath, horse ...
Time: 80s
Place: latin america, mexico
⇓ similarity ⇓
68%
 6.2
 5K
Thin Ice (2011)
Genre: Comedy, Crime, Drama
Country: USA
Duration: 93 min.
Story: 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.
Style: semi serious, humorous, realistic, twists and turns, clever ...
Plot: nothing goes right, unlikely criminals, comedy of errors, crime gone awry, disorder, dishonesty, cons and scams, manipulation, dark humor, salesman, insurance, cold ...
Time: 21st century, contemporary
Place: usa, wisconsin
⇓ similarity ⇓
66%
 4.7
 757
Underworld (1996)
Genre: Comedy, Thriller
Country: USA, Canada
Duration: 95 min.
Story: A crook sets out to get revenge on the thugs who hurt his father in this bloody noir-style crime drama. After being released from prison, Johnny Crown (Denis Leary) goes after Frank (Joe Mantegna), one of the mobsters involved in a series of ...
Style: realistic, semi serious, exciting, neo noir, rough ...
Plot: vengeance, gangsters, crimes, prison, buddies, criminal heroes, rivalry, dishonesty, partners, criminal's revenge, cons and scams, massacre ...
Time: 90s
⇓ similarity ⇓
60%
Everything Must Go (1996)
Genre: Comedy, Drama
Country: Belgium
Duration: 105 min.
Story: Tony is a homosexual law student who quits his studies. With a van and a handful of cash, he hits the road hoping to become a salesman. This, however, turns out to be harder than he expected.
Style: semi serious, realistic, humorous, clever, witty ...
Audience: boys' night
Plot: friends, dark humor, disorder, foe turned friend, graphic violence, crimes, buddies, dishonesty, gender, unlikely partners, nothing goes right, gays and lesbians ...
Time: 90s, 20th century
Place: europe, belgium
⇓ similarity ⇓
58%
Movie in collections
 5.9
 1K
Frauds (1993)
Genre: Comedy, Crime, Thriller
Country: Australia
Duration: 90 min.
Story: The film is a story of the ways in which insurance investigator Roland Copping interferes in and manipulates the lives of others with outrageous games and gimmicks. Eventually he becomes involved in an escalating vendetta with a couple who make an ...
Style: realistic, semi serious, cynical, witty, humorous ...
Plot: heist, cons and scams, woman in danger, rivalry, prank, mind game, crimes, dishonesty, terrorism, disorder, blackmail, insurance scam ...
Time: 90s
⇓ similarity ⇓
57%
 5.4
 2K
Body Count (1998)
Genre: Crime, Drama, Thriller
Country: USA
Duration: 85 min.
Story: A group of thieves attempt to rob an art gallery, but when plans backfire and one of the men winds up dead, the group head down south, running afoul of the law. Along the way, they meet up with a seductive con artist with ideas of her own.
Style: neo noir, realistic, serious, suspenseful, rough ...
Audience: boys' night
Plot: heist, on the road, murder, criminal heroes, partners, on the run, misfit partners, law enforcement, rivalry, crime gone awry, crimes, dishonesty ...
Time: 90s
Place: boston, usa
⇓ similarity ⇓
53%
All Is Bright (2013)
Genre: Comedy, Drama
Country: USA
Duration: 107 min.
Story: Two French Canadian ne’er-do-wells travel to New York City with a scheme to a get rich quick selling Christmas trees.
Style: semi serious, humorous, feel good, captivating, realistic
Plot: criminal heroes, fish out of water, going straight, nothing goes right, reluctant partners, partners, odd couple, disorder, misfit, cons and scams, crimes, dishonesty ...
Time: 21st century, contemporary
Place: new york, usa
⇓ similarity ⇓
52%
A Good Night to Die (2003)
Genre: Action, Comedy, Thriller
Country: USA
Duration: 100 min.
Story: One day in the life of a hit man, Ronnie, who spends it trying to save the life of fellow hit man, August, who he had brought into the business three years ago. August has become a real problem for some of the bosses around town, and Ronnie will ...
Style: semi serious, realistic, humorous, exciting, tense ...
Audience: boys' night
Plot: hitman, nothing goes right, betrayal, crime gone awry, criminal's revenge, working undercover, dishonesty, gangsters, crimes, criminal heroes, dark humor, disorder ...
Time: 21st century, contemporary
⇓ similarity ⇓
50%
 5.3
 208
Hustle (2000)
Genre: Comedy, Crime, Drama
Country: Germany, Canada
Duration: 100 min.
Story: Maya and Tony are a modern-day Bonnie and Clyde. Maya seduces businessmen while Tony copies their credit cards. It's a smooth con until one of their victims, Pierce, pulls a gun. Instead of killing them, Pierce offers the desperate couple a ...
Style: serious, realistic, twists and turns, rough, neo noir ...
Plot: femme fatale, crimes, crime gone awry, criminal heroes, heist, couples, disorder, dishonesty, betrayal, intrigue, rivalry, gambling ...
Time: 90s, 20th century
⇓ similarity ⇓
49%
 6.9
 76K
Bottle Rocket (1996)
Genre: Comedy, Crime, Drama
Country: USA
Duration: 91 min.
Story: 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 hair-brained scheme for an as-yet-unspecified crime spree that ...
Style: humorous, witty, talky, semi serious, realistic ...
Audience: boys' night
Plot: robbery, theft, heist, thief, crimes, disorder, self discovery, nothing goes right, sibling relationship, partners in crime, cons and scams, criminal heroes ...
Time: 20th century, 90s
Place: texas, usa
⇓ similarity ⇓
48%
 6.2
 1K
Slither (1973)
Genre: Comedy, Thriller, Crime
Country: USA
Duration: 97 min.
Story: While searching for a small fortune of embezzled money, an ex-con, a small-time bandleader, his doting wife and a kooky drifter find themselves being followed. Their chase takes them to trailer camps, bingo halls, laundromats and ultimately, a ...
Style: semi serious, realistic, humorous, road movie, offbeat
Plot: heist, diner, on the road, cons and scams, disorder, chase, criminal heroes, dishonesty, on the run, going straight, crimes, money ...
Time: 70s
⇓ similarity ⇓
47%
Shakes the Clown (1991)
Genre: Comedy, Crime, Drama
Country: USA
Duration: 87 min.
Story: Shakes plods about his duties as party clown, and uses all of his free time getting seriously drunk. Binky, another clown, wins the spot on a local kiddie show, which depresses Shakes even more, and his boss threatens him with unemployment if he ...
Style: humorous, semi serious, disturbing, surreal, dark ...
Plot: alcohol abuse, clown, false accusation, rescue, dark humor, nothing goes right, frame up, crimes, disorder, murder, boyfriend girlfriend relationship, hostage ...
Time: 90s
Place: plymouth
⇓ similarity ⇓
47%
Fish in a Barrel (2001)
Genre: Comedy, Drama
Country: USA
Duration: 85 min.
Story: 6 gun wielding people are trapped in a NY loft with $4 million in stolen diamonds.
Style: suspense, semi serious, cynical, humorous, realistic ...
Plot: crime gone awry, rivalry, heist, betrayal, dishonesty, crimes, law enforcement, criminal's revenge, disorder, alcohol abuse, brother brother relationship, diamond ...
Time: contemporary, 21st century
Place: new york, usa
⇓ similarity ⇓
46%
 4.4
 283
Dead in France (2012)
Genre: Comedy, Crime, Thriller
Country: UK
Duration: 88 min.
Story: A socially-challenged hitman's French retirement is ruined by the dodgy Brits on the Cote d'Azur.
Style: realistic, semi serious, humorous, suspenseful, neo noir
Plot: disorder, dark humor, criminal heroes, dishonesty, crimes, hitman, graphic violence, cons and scams, gunfight, female assassin, male nudity, drunkenness ...
Time: contemporary, 21st century
Place: south of france
⇓ similarity ⇓
46%
Movie in collections
Kill Your Darlings (2006)
Genre: Comedy, Drama
Country: Sweden, USA
Duration: 94 min.
Story: A desperate young writer is lured on a wild ride through the desert by a mysterious woman in this darkly comic take on the all-American road trip. Along the way they cross paths with a hapless mobster, a 6 foot transvestite and a lovesick housewife, ...
Style: road movie, semi serious, psychological, realistic, humorous ...
Plot: desert, supportive spouse, on the road, looking for love, crimes, writer's life, criminal heroes, dark humor, hollywood, writers, gangsters, celebrity culture ...
Time: 21st century, contemporary
Place: las vegas, nevada
⇓ similarity ⇓
44%
 6.7
 1K
Bone (1972)
Genre: Comedy, Drama, Thriller
Country: USA
Duration: 95 min.
Story: A thief breaks into the home of a wealthy, happily married Beverly Hills couple. He soon finds out, though, that the couple is neither as wealthy as he thought they were and are not as happily married as they appeared.
Style: realistic, semi serious, talky, cynical, witty ...
Plot: hostage, interracial relations, rapist, dark humor, couples, society, crime gone awry, opposites attract, crimes, crumbling marriage, social differences, social decay ...
Time: 70s
Place: beverly hills, usa, los angeles
⇓ similarity ⇓
44%
 5.8
 328
Hotel Oasis (2001)
Genre: Comedy, Crime, Drama, Music
Country: USA, Canada
Duration: 97 min.
Story: The life of motel owner is turned upside down by a femme-fatale lounge singer and her abusive manager.
Style: semi serious, humorous, cynical, realistic, witty ...
Plot: murder, crimes, cons and scams, dark humor, disorder, dishonesty, unlikely criminals, nothing goes right, twins, husband wife relationship, fatal accident, sister sister relationship ...
Time: contemporary
Place: kansas, usa
⇓ similarity ⇓
43%
Like a Fish Out of Water (1999)
Genre: Comedy, Crime, Thriller
Country: France
Duration: 90 min.
Story: A seductive femme fatale (Monica Bellucci) and two con men -- one cool as ice, and one who just likes to "ice" his victims -- enlist a mild-mannered, unsuspecting man in their mission to steal a rare and valuable fish. They plan to sell it ...
Style: biting, cynical, suspense, realistic, semi serious ...
Plot: gangsters, couples, disorder, femme fatale, criminal heroes, dishonesty, unlikely criminals, partners, crime gone awry, forgery, crimes, heist ...
Time: 90s
⇓ similarity ⇓
41%
Durval Records (2002)
Genre: Comedy, Drama, Music, Thriller
Country: Brazil
Duration: 96 min.
Story: Durval and his mother Carmita live at the back of "Durval Discos", a record store they own in São Paulo, specializing in vinyl records. They lead a boring and unattractive life, until the day Durval hires a maid, Celia, to help his mother ...
Style: semi serious, humorous, feel good, realistic, offbeat
Plot: farce, comedy of errors, eccentric family, life turned upside down, dark humor, missing child, family relations, disorder, parents and children, crime gone awry, crimes, family problems ...
Time: 20th century, 90s
Place: brazil, sao paulo brazil
⇓ similarity ⇓
41%
Movie in collections
 5.8
 11K
Novocaine (2001)
Genre: Comedy, Crime, Drama, Thriller
Country: USA
Duration: 95 min.
Story: A dentist finds himself a murder suspect after a sexy patient seduces him into prescribing her drugs
Style: suspenseful, captivating, humorous, twists and turns, tricky ...
Plot: murder, femme fatale, dark humor, false accusation, frame up, dentist, betrayal, crimes, life turned upside down, drug use, dishonesty, unlikely criminals ...
Time: contemporary
Place: arizona, usa, france
⇓ similarity ⇓
40%
 6.3
 3K
Dollars (1971)
Genre: Comedy, Crime, Drama
Country: USA
Duration: 121 min.
Story: A bank security expert plots with a call girl to rob the safety deposit boxes of three very different criminals from a high-tech bank in Hamburg.
Style: cynical, semi serious, realistic, clever, humorous ...
Audience: boys' night
Plot: heist, prostitute, disorder, hostage, partners, law enforcement, master criminal, on the run, criminal heroes, lovers on the run, rivalry, dishonesty ...
Time: 70s, 20th century
Place: germany, europe, copenhagen, hamburg germany
⇓ similarity ⇓
40%
 5.8
 566
Now or Never (2000)
Genre: Comedy, Crime, Thriller
Country: Germany
Duration: 95 min.
Story: No overview found.
Style: semi serious, realistic, humorous, captivating, exciting
Plot: retirement home life, heist, bank, disorder, unlikely criminals, elderly, friendship, down on your luck, retirement home, crimes, dishonesty, criminal heroes ...
Time: 90s, 20th century
Place: germany
⇓ similarity ⇓
39%
Cold Around the Heart (1997)
Genre: Crime, Drama, Thriller
Country: USA
Duration: 96 min.
Story: A jewel thief moves towards a reunion of revenge with his lover, who pushed him out of their speeding getaway car.
Style: cynical, tense, captivating, realistic, serious ...
Plot: chase, hitchhiker, dishonesty, crimes, love and romance, betrayal, lovers on the run, rivalry, on the run, crime gone awry, criminal's revenge, on the road ...
Time: 90s
⇓ similarity ⇓
39%
 6.5
 3K
The Swindle (1997)
Genre: Comedy, Crime, Thriller
Country: France, Switzerland
Duration: 101 min.
Story: Betty and Victor are a pair of scam artists. One day Betty brings in Maurice, a treasurer of a multinational company. Maurice is due to transfer 5 millions francs out of Switzerland, and Betty is convinced he plans to steal that money.
Style: semi serious, humorous, realistic, clever, witty ...
Plot: gambling, casino, cons and scams, heist, crimes, disorder, intrigue, crime gone awry, dishonesty, forgery, hidden identity, criminal heroes ...
Time: 90s
Place: swiss alps
⇓ similarity ⇓
39%
 3.5
 130
Lansdown (2001)
Genre: Thriller, Comedy
Country: USA
Duration: 80 min.
Story: In this dark comedy, defense lawyer Jake Jorgenson's carefully constructed life begins to unravel when he kills his wife's lover.
Style: cynical, semi serious, humorous, realistic, witty ...
Plot: infidelity, murder, goofy hero, crime gone awry, vengeance, dishonesty, crimes, dark humor, couples, disorder, husband wife relationship, adultery ...
Time: contemporary
Place: new jersey
⇓ similarity ⇓
39%
 5.6
 766
Preggoland (2014)
Genre: Comedy, Drama
Country: Canada
Duration: 109 min.
Story: A 35-year-old woman fakes being pregnant to fit in with her friends.
Style: semi serious, humorous, captivating, feel good, light ...
Audience: girls' night
Plot: dishonesty, family relations, life turned upside down, disorder, best friends, faked pregnancy, lie, society, strong female presence, bittersweet, pregnancy, unfulfillment ...
Time: 21st century, contemporary
Place: canada
⇓ similarity ⇓
39%