5 Popular Hollywood Movies That Glorify Illegal Gambling

Written By Cheryl Coward on May 19, 2023
Popular movies that glorify illegal gambling, from playca.com

The setting is familiar: beautiful people, expensive formal attire, classic cocktails, opulent surroundings, and baccarat.

Countless movies featuring gambling include these elements as fans watch in awe at the cosmopolitan lifestyle of gamblers with deep pockets. While many of these flicks serve as cautionary tales about addiction and underground betting houses, plenty of others glamorize unlawful gambling.

While Hollywood often portrays scenes of gambling, California sports betting remains illegal, but the industry has launched in over 35 other states.

Illegal gambling in film and television

Hollywood movies and TV shows have depicted illegal gambling for decades. There is a long list of productions that fit this criteria.

It continues to this day. A planned comedy series centered on sports betting will appear later this year on Max, titled How to Be a Bookie.

The series follows Los Angeles bookie struggling with the legalization of sports betting in California. It will be set in and filmed in Los Angeles, while California is still several steps away from legalizing sports betting.

But that show has yet to air. As the sports betting industry continues to expand, here is a list of some of the most popular films that glorify illegal gambling.

The Sting (1973)

With an all-star cast featuring Paul Newman, Robert Redford, and Robert Shaw, The Sting is the most successful gambling-related movie in American film history. It won seven Academy Awards, including Best Picture and Best Actor (Redford).

Set in 1930s Chicago amid the Great Depression, the plot revolves around the comedic capers of two con men played by Redford and Newman. Redford’s character, Johnny Hooker, and a friend successfully pull off a grift that provides them with $11,000. But, they don’t realize the subject of the con is the numbers runner for a ruthless mob boss, Doyle Lonnegan, who puts a hit on Hooker when he realizes who stole his money.

The mob boss kills Hooker’s friend who helped him in the robbery.  Lonnegan sets out to get revenge on Hooker, and along with the FBI, chases his accomplice, a renowned con man named Henry Gondorff, played by Newman.

As the movie progresses and the duo sets out to get revenge, viewers are treated to several scenes of illegal gambling houses. From backroom neighborhood card dens to the deluxe casino run by the mob boss, and one set up by the Hooker and Gondorff as part of the revenge con. The backroom venues are packed, vibrant, and full of action, with brothels attached. The dens attract all sectors of society, from working-class folk to police officers.

The underground casinos in the movie were illegal, but law enforcement looked the other way as patrons enjoyed card games, placed bets on horse races, and more.

Octopussy (1983)

Typical of a James Bond movie, Octopussy includes high-stakes gambling in a luxurious setting.

The thirteenth film in the 007 series centers around a counterfeit of a priceless Fabergé egg owned by an Afghan prince in cahoots with a crooked Soviet general and a beautiful woman named Octopussy. The Afghan prince double crosses Octopussy, and she switches her allegiance to Bond, played by Roger Moore.

Gambling is featured in one of the movie’s iconic scenes. Early in the film, Bond tricks the prince, Kamal Khan, into purchasing a counterfeit Fabergé at an auction. Soon after, Bond appears unannounced at a backgammon game at the prince’s palace. Khan always has the upper hand against his opponents because he plays with loaded dice. Bond notices the con and uses it to his advantage. He earns the homicidal ire of Khan when he pulls out the real egg as a stake in the game.

It is a masterful scene full of tension, intrigue, and glamour and sets the tone for the rest of the movie with Khan on the warpath for Bond.

ALSO READ: Revisiting The Classic Film ‘California Split’ With Writer Joseph Walsh

Harlem Nights (1989)

Set in 1918, Harlem Nights is a rollicking hilarious crime comedy featuring the cream of the crop of African American comedians and entertainers: Richard Pryor, Redd Foxx, Robin Harris, Eddie Murphy and his older brother Charlie, Della Reese, Arsenio Hall, Jasmine Guy, Thomas Mikal Ford, and a young Lela Rochon. Michael Lerner also has a significant role as an Italian crime boss, Bugsy Calhoune. If you want to be in stitches laughing for an entire movie, watch this film.

Pryor and Lerner play owners of posh underground “after-hours clubs.” Nearly the entire movie is set in these illegal gambling venues, including the one-room craps den where Pryor’s character, Sugar Ray, began his career.

Years later, his room evolves into a spacious private club with tables, entertainment, bars, and a brothel run by Reese’s character. Everyone in the club is dressed to the nines, having a good time, gambling, dancing, and drinking.

Ray and Calhoune are at odds with each other during the movie. Ray successfully cons Calhoune out of a large sum of money from the winnings of a boxing match and burns his club down before skipping town. The cinematography and costume design make Harlem Nights one of the most visually appealing films glamorizing illegal gambling.

The House (2017)

With Amy Poehler and Will Ferrell leading, The House takes viewers on a far-fetched yet funny ride. The premise revolves around two suburban parents setting up an underground casino along with a down-and-out friend who wants to earn money to help entice his wife who left him.

Poehler and Ferrell play Kate and Scott Johansen, who need to make money quickly to pay for their daughter’s tuition when a scholarship she won from the city council gets defunded. They team up with their neighbor, Frank Theodorakis, played by Jason Mantzoukas, to open an underground casino that quickly becomes a success and eventually draws the attention of a police officer and the crooked city councilor who rescinded the scholarship.

The casino, set in Theodorakis’ house, begins as a bare-bones venue with basic and DIY furniture. Eventually, it resembles a mini-casino resort with table games, live entertainment, and a pool area.

The House is a funny movie good for an hour and a half of escapism and a lighthearted take on illegal gambling.

Molly’s Game (2017)

Based on a true story, Molly’s Game follows the high-stakes poker career of former elite skier Molly Bloom. After suffering a devastating fall in an attempt to qualify for the Olympics, Colorado native Bloom delayed plans to go to law school and headed to Los Angeles instead. She eventually begins working as an office manager for a real estate developer who runs underground poker games. The games attract high-rollers like pro athletes and entertainers.

Her boss fires her when he notices how successful she is at organizing games and bringing in new players. So, Bloom begins running her own poker games in a swank hotel penthouse suite. Her upgraded poker games include concierge-like service for the players as she caters to their every whim.

After a falling out with a celebrity player who is one of the main draws for other players, she moves to New York and starts anew with an upscale poker game with multiple rooms and an area for illegal sports betting.

The walls come crashing down on Bloom as she becomes a target of an FBI investigation due to the presence of Russian mafia members at her games. Nevertheless, until that point, viewers get an extended glimpse into the lifestyle and vices of the players and organizers of high-end underground poker games.

Photo by AP Photo/Charles Sykes
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Cheryl Coward

Cheryl Coward is a contributor for PlayCA with a background in sports journalism. She started her career as a news reporter in Washington, DC. She’s a die-hard women’s basketball fanatic and founded the website Hoopfeed.com as a result of that passion. She has extensive experience covering gambling and sports betting in California, including coverage of the Prop 26 vs. Prop 27 election battle.

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