Movies Like The Road to Ruin

If you liked The Road to Ruin (1913), a movie directed by George Gray, 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
Ballad of a Small Player (2025)
★ 5.8/10
Amid the glittering casinos of Macau, a gambler running from his past—and his debts—becomes fascinated by an enigmatic woman at the baccarat table.
2
Easy Money (1983)
★ 6/10
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.
3
The Way Back (2020)
★ 6.6/10
A former basketball all-star, who has lost his wife and family foundation in a struggle with addiction, attempts to regain his soul and salvation by becoming the coach of a disparate ethnically mixed high school…
4
The Wonderful Story of Henry Sugar (2023)
★ 7.3/10
A rich man learns about a guru who can see without using his eyes. He sets out to master the skill in order to cheat at gambling.
5
A Street Cat Named Bob (2016)
★ 7.9/10
James Bowen, a homeless busker and recovering drug addict, has his life transformed when he meets a stray ginger cat.
6
The Hustler (1961)
★ 7.7/10
Fast Eddie Felson is a small-time pool hustler with a lot of talent but a self-destructive attitude. His bravado causes him to challenge the legendary Minnesota Fats to a high-stakes match.
7
Bugsy (1991)
★ 6.3/10
New York gangster Ben 'Bugsy' Siegel takes a brief business trip to Los Angeles. A sharp-dressing womanizer with a foul temper, Siegel doesn't hesitate to kill or maim anyone crossing him. In L.A. the life, the movies…
8
Leaving Las Vegas (1995)
★ 7.3/10
Ben Sanderson, an alcoholic Hollywood screenwriter who lost everything because of his drinking, arrives in Las Vegas to drink himself to death. There, he meets and forms an uneasy friendship and non-interference pact…
9
Angels with Dirty Faces (1938)
★ 7.5/10
Childhood chums Rocky Sullivan and Jerry Connelly grow up on opposite sides of the fence: Rocky matures into a prominent gangster, while Jerry becomes a priest, tending to the needs of his old tenement neighborhood.
10
Uncut Gems (2019)
★ 7.2/10
A charismatic New York City jeweler always on the lookout for the next big score makes a series of high-stakes bets that could lead to the windfall of a lifetime. Howard must perform a precarious high-wire act…
11
Casino (1995)
★ 8/10
In Las Vegas, two best friends-a casino executive and a Mafia enforcer--compete for a gambling empire and a fast-living, fast-loving socialite.
12
The Man with the Golden Arm (1955)
★ 7.1/10
When illegal card dealer and recovering heroin addict Frankie Machine gets out of prison, he decides to straighten up. Armed with nothing but an old drum set, Frankie tries to get honest work as a drummer. But when his…
13
Rounders (1998)
★ 7/10
Poker addict Mike McDermott knows the game inside out, but loses his money one night in a game to Russian-American gangster Teddy KGB. Promising his partner Jo he'll give up, he meets up with best friend Lester 'Worm'…
14
Babylon (2022)
★ 7.3/10
A tale of outsized ambition and outrageous excess, tracing the rise and fall of multiple characters in an era of unbridled decadence and depravity during Hollywood's transition from silent films to sound films in the…
15
Croupier (1998)
★ 6.7/10
Jack Manfred is an aspiring writer who to make ends meet, takes a job as a croupier. Jack remains an observer, knowing that everything in life is a gamble and that gamblers are born to lose. Inevitably, he gets sucked…
16
The Disaster Artist (2017)
★ 7.1/10
An aspiring actor in Hollywood meets an enigmatic stranger by the name of Tommy Wiseau, the meeting leads the actor down a path nobody could have predicted; creating the worst movie ever made.
17
Overboard (2018)
★ 6.7/10
A spoiled, wealthy yacht owner is thrown overboard and becomes the target of revenge from his mistreated employee.
18
Cocktail (1988)
★ 6.1/10
After being discharged from the Army, Brian Flanagan moves back to Queens and takes a job in a bar run by Doug Coughlin, who teaches Brian the fine art of bar-tending. Brian quickly becomes a patron favorite with his…
19
The Hustle (2019)
★ 6.2/10
Two female scam artists, one low rent and the other high class, compete to swindle a naïve tech prodigy out of his fortune. A remake of the 1988 comedy "Dirty Rotten Scoundrels."
20
Ocean's Thirteen (2007)
★ 6.7/10
Danny Ocean's team of criminals are back and composing a plan more personal than ever. When ruthless casino owner Willy Bank doublecrosses Reuben Tishkoff, causing a heart attack, Danny Ocean vows that he and his team…