High Stakes And Big Wins: 21 of the Best Gambling Movies Of All Time – Blavity

Gambling movies are always exciting, showing people playing games like poker or blackjack where they can win or lose a lot of money. These movies often take place in casinos or secret gambling places, where everything feels tense and anything can happen. What makes these movies interesting is not just the games, but also the stories of people taking big risks, sometimes just for the thrill of it.

At the heart of these movies is the idea of taking risks for a reward. The main characters often want to win big or change their lives, which makes the stakes very high. This makes the movies suspenseful, as the characters can either win a lot or lose everything. Gambling movies also show the downsides of this world, like addiction and betrayal, giving a look at the consequences of risky choices.

These films also touch on themes like luck, fate, and chasing dreams, often set in flashy places like Las Vegas or hidden gambling spots. They show that, like in life, gambling involves taking chances with uncertain outcomes. Whether the story is about someone looking for a new start or a skilled player trying to win, these movies give a glimpse into how closely success and failure can be linked.

“Dolemite Is My Name” (2019)

IMDB: 7.2/10
Rotten Tomatoes: 97%
Where to Watch: Netflix

Eddie Murphy plays Rudy Ray Moore, a struggling comedian in the 1970s who reinvents himself as the vulgar, larger-than-life character Dolemite. His journey includes creating and promoting films that push boundaries, often involving high-stakes bets and risky ventures. While you’ll not see casino tables The film vividly portrays Moore’s gamble on his unorthodox career path and the cultural impact of his work.

“Beats” (2019)

IMDB: 6.4/10
Rotten Tomatoes: 88%
Where to Watch: Netflix

A gripping drama, 2019’s Beats follows a young, reclusive music prodigy who is discovered by a former music producer struggling with his own demons. As the mentor helps the prodigy find his voice, the story touches on themes of personal and financial risk. The subplot involving gambling adds tension, reflecting the precarious nature of their lives and dreams. No one said breaking into the music scene was easy, and there are always going to be places where any musical hopeful will have the roll the dice. Beats explores that perfectly.

“How High” (2001)

IMDB: 6.2/10
Rotten Tomatoes: 25%
Where to Watch: Google Play, Amazon Prime Video, Apple TV, Fandango at Home

How High is a stoner comedy film directed by Jesse Dylan and stars Method Man and Redman, who are well-known rappers and actors. The film blends humor with supernatural elements, revolving around two friends who use marijuana to achieve academic success and navigate the challenges of college life. What makes How High a gambling movie? In this case, it’s the (literal) high stakes involved.

The lead duo take a lot of risks – though they’re not exactly the kinds of risks you’d find yourself taking in everyday life, like trying to dig up the grave of a, quote, “smart dead guy” and smoke his remains in hopes of getting a better score on one’s midterms. Schemes are tried, schemes fail, and you’ll find yourself hoping this next one pulls through.

“Life” (1999)

IMDB: 6.8/10
Rotten Tomatoes: 52%
Where to Watch: Netflix, Google Play, Apple TV, Fandango at Home, Amazon Prime Video

Life is a comedy-drama film directed by Ted Demme, featuring an ensemble cast led by Eddie Murphy and Martin Lawrence. The film is set primarily in the 1930s and 1940s in Mississippi, amidst the backdrop of racial segregation and the Great Depression. It focuses on the lives of two men who find themselves trapped in the harsh realities of a life sentence in a state penitentiary. The setting plays a significant role in highlighting the injustices and societal issues of the time.

“All Day And A Night” (2020)

IMDB: 6/10
Rotten Tomatoes: 53%
Where to Watch: Netflix

Another Netflix original on our list of movies about gambling, All Day and A Night follows Jahkor Abraham Lincoln, a young man whose criminal life and involvement in gang culture lead to his imprisonment. The story explores his reflections on his past decisions and the generational cycle of crime and poverty. The theme is similar to what you will find in gambling movies. It is metaphorical, representing the high risks and consequences of his choices.

“Hoodlum” (1997)

IMDB: 6.3/10
Rotten Tomatoes: 43%
Where to Watch: Tubi, Pluto TV, The Roku Channel, Brown Sugar, Sling TV, Amazon Prime VIdeo, YouTube TV, Fandango at Home, Google Play, Apple TV

Hoodlum is a crime drama film directed by Bill Duke and set in the 1930s Harlem. The film stars Laurence Fishburne as Bumpy Johnson and a strong supporting cast including Tim Roth, Vanessa Williams, and Queen Latifah. The story revolves around Bumpy Johnson’s rise in the criminal underworld and his struggles against powerful adversaries in the era of Prohibition. Bumpy is a complex figure who navigates the treacherous world of organized crime with intelligence and ruthlessness.

“The Banker” (2020)

IMDB: 7.3/10
Rotten Tomatoes: 78%
Where to Watch: Apple TV, Amazon Prime Video

The Banker is based on the true story of two African-American entrepreneurs, played by Anthony Mackie and Samuel L. Jackson, who pose as a wealthy businessman and a janitor to infiltrate the banking industry and expose racial discrimination. The high-stakes gambles they take involve deceptive strategies and bold moves to achieve their goals.

“Rim Of The World” (2019)

IMDB: 5.3/10
Rotten Tomatoes: 31%
Where to Watch: Netflix

Rim of the World is a sci-fi adventure film that follows a group of teenagers who must defend Earth from an alien invasion after a summer camp is interrupted by extraterrestrial forces. In one subplot, a high-stakes casino scene adds a layer of excitement and danger, reflecting the broader risks faced by the characters. While it’s not entirely a movie about gambling, the high stakes thrills packed into that scene certainly give it a proud spot on this list.

“Da 5 Bloods” (2020)

IMDB: 6.5/10
Rotten Tomatoes: 92%
Where to Watch: Netflix

Starring Delroy Lindo, Jonathan Majors, Clarke Peters, and many more, Da 5 Bloods is a 2020 Spike Lee film that was quickly lauded following its release, including be nominated for an Oscar and a SAG award. It was also named the best film of 2020 by the National Board of Review.

Da 5 Bloods follows four African-American veterans who return to Vietnam to find the remains of their fallen squad leader and recover a stash of gold they buried during the war. The high-stakes nature of their quest mirrors the risks involved in gambling, as they navigate both the perils of the jungle and their personal conflicts.

“Set It Off” (1996)

IMDB: 6.5/10
Rotten Tomatoes: 92%
Where to Watch: Paramount +, YouTube, Hulu, fuboTV, Sling TV, The Roku Channel, Amazon Prime, Apple TV, Google Play, Fandango at Home

Desperate times lead to desperate measures, especially for four women who are all hard up for cash as portrayed in Set it Off. They decide to get into the business of robbing banks – but one of the women’s brothers is a cop, and he’s hot on their trail to take them down. They begin to distrust each other as the plot thickens, all leading to one big climactic robbery that will have you on the edge of your seat. While primarily a heist film, it features elements of gambling and risk-taking. Set it Off stars Jada Pinkett Smith, Queen Latifah, Vivica A. Fox, and Kimberly Elise.

“One Night In Miami…” (2020)

IMDB: 7.1/10
Rotten Tomatoes: 98%
Where to Watch: Amazon Prime Video

Featuring famous faces in history, One Night in Miami… imagines a fictional meeting between Muhammad Ali, Malcolm X, Sam Cooke, and Jim Brown after Ali’s title victory. They discuss their roles in the civil rights movement and the risks they face in their respective careers. The high-stakes conversations and decisions they make serve as a metaphor for the broader societal gambles they are involved in.

“Sylvie’s Love” (2020)

IMDB: 6.8/10
Rotten Tomatoes: 94%
Where to Watch: Amazon Prime Video

Written and produced by Eugene Ashe and starring Tessa Thompson, Sylvie’s Love is a 2020 romantic drama that follows the eponymous Sylvie, a woman who falls in love with a jazz musician in the 1950s. The film portrays their relationship against a backdrop of glamorous entertainment and high-stakes decisions, with gambling representing the risks and rewards of their personal choices.

“Top Five” (2014)

IMDB: 6.4/10
Rotten Tomatoes: 85%
Where to Watch: Hulu, fuboTV, Sling TV, The Roku Channel, Amazon Prime Video, Paramount+, YouTube, Google Play, Apple TV, Fandango at Home

Chris Rock stars as a comedian struggling with his career and personal life in Top Five. The film includes a subplot involving high-stakes gambling and risky decisions as part of the entertainment industry’s backdrop. Rock’s character must navigate these risks while balancing his comedic ambitions with his personal challenges.

“Uncut Gems” (2019)

IMDB: 7.4/10
Rotten Tomatoes: 91%
Where to Watch: YouTube, Google Play, Fandango at Home, Amazone Prime Video, Apple TV

In this cinematic gem (no pun intended,) Uncut Gems sees Adam Sandler starring as Howard Ratner, a jeweler with a gambling addiction who bets everything on a high-stakes basketball game in an attempt to solve his financial problems. The film is a high-octane thriller that depicts Howard’s risky behavior and its consequences, reflecting the literal and metaphorical gambles he takes.

“Idlewild” (2006)

IMDB: 6.2/10
Rotten Tomatoes: 47%
Where to Watch: Starz, YouTube, Hulu, Sling TV, The Roku Channel, Amazon Prime Video, Philo, Google Play, Apple TV, Fandango at Home

For musical fans who want movies about gambling with an amazing soundtrack, it’s time to check out Idlewild. Idlewild is a musical drama film directed by Bryan Barber, featuring André 3000 (André Benjamin) and Big Boi (Antwan Patton) of OutKast, who also co-produced the film. Set in the 1930s, the film combines elements of music, drama, and crime, and is set in the fictional town of Idlewild, Georgia. It explores themes of ambition, loyalty, and the transformative power of music.

“Judas And The Black Messiah” (2021)

IMDB: 7.4/10
Rotten Tomatoes: 96%
Where to Watch: YouTube, Hulu, Amazon Prime Video, Apple TV, Fandango at Home

“You can kill a revolutionary, but you can’t kill the revolution” – so goes the tagline of Judas And The Black Messiah. This film tells the story of Fred Hampton, chairman of the Illinois chapter of the Black Panther Party, and his betrayal by FBI informant William O’Neal. The high-stakes nature of Hampton’s revolutionary activities and the dangerous gamble O’Neal takes in his undercover role are central to the film’s narrative.

Judas And The Black Messiah was nominated for six Academy Awards, where it won two. It was also dazzled with other awards from the African-American Film Critics Association Awards, the American Film Institute Awards, the BET Awards, and many others.

“Hustle And Flow” (2005)

IMDB: 7.3/10
Rotten Tomatoes: 83%
Where to Watch: Paramount+, YouTube, Hulu, fuboTV, Sling TV, The Roku Channel, Amazon Prime Video, Google Play, Apple TV, Fandango at Home

Set in Memphis, Tennessee, Hustle and Flow follows DJay (Terrence Howard), a small-time hustler and pimp who dreams of becoming a successful hip hop musician. While not strictly one of the best gambling movies, the movie deals with themes of risk-taking, hustling, and betting on oneself – concepts often associated with gambling narratives.

“All About the Benjamins” (2002)

IMDB: 5.8/10
Rotten Tomatoes: 31%
Where to Watch: Tubi, YouTube, Google Play, Fandango at Home, Amazon Prime Video, Apple TV

All About the Benjamins is a high-energy action-comedy directed by Kevin Bray. The film stars Ice Cube as a seasoned bounty hunter named Bucum Jackson, who is known for his sharp skills and no-nonsense attitude. His latest assignment leads him to a high-stakes, adrenaline-pumping adventure involving diamond thieves and illegal gambling.

“If Beale Street Could Talk” (2018)

IMDB: 7.1/10
Rotten Tomatoes: 95%
Where to Watch: PLEX, YouTube, Google Play, Apple TV, Amazon Prime Video, Fandango at Home

Directed by Barry Jenkins and based on James Baldwin’s novel, If Beale Street Could Talk tells the story of Tish Rivers, a young African-American woman whose fiancé, Fonny Hunt, is wrongfully accused of a crime he didn’t commit. The film explores the personal and systemic struggles they face, including financial and legal challenges. Although gambling is not a central theme, the high stakes of their fight for justice and the gamble of placing hope in a flawed legal system reflect the broader risks and uncertainties in their lives.

“Charm City Kings” (2020)

IMDB: 6.6/10
Where to Watch: YouTube, Google Play, Apple TV, Amazon Prime Video, Fandango at Home

Directed by Angel Manuel Soto, the film focuses on Mouse, a 14-year-old boy in Baltimore who dreams of becoming a professional street bike rider. His aspirations are complicated by the dangerous realities of street racing and the influence of a local gang. The gambling element comes into play with the high-stakes nature of the racing culture, as Mouse navigates the risks and pressures of trying to achieve his dreams while avoiding the pitfalls of his environment.