20 Movies That Glorified Real-Life Criminals (And Got Away With It)

Movies have always been drawn to the lives of criminals, often turning them into captivating characters. These films frequently blur the line between showing what actually happened and making audiences feel sympathy for people who committed serious crimes. We often end up cheering for bank robbers or drug kingpins thanks to great acting and exciting filmmaking. Here’s a list of twenty films that tell the stories of real-life criminals in a particularly stylish and engaging way.

‘The Wolf of Wall Street’ (2013)

Directed by Martin Scorsese, this film tells the true story of Jordan Belfort, a stockbroker who made a fortune through dishonest and illegal practices. Leonardo DiCaprio plays Belfort, showcasing his captivating but corrupt personality and wild lifestyle on Wall Street, fueled by drugs and ill-gotten gains. The movie highlights how Belfort’s wealth and excess ultimately led to his arrest and imprisonment, portraying the excitement and danger of his fraudulent schemes with a fast-paced energy.

‘Goodfellas’ (1990)

This gripping crime drama follows the life of Henry Hill, a man involved with the mafia, over many years. Ray Liotta plays Hill, a gangster drawn in by the lavish lifestyle of the Lucchese crime family. Director Martin Scorsese tells the story at a quick pace, showing both the loyalty and the violence within organized crime. The film explores how appealing power can be, while also revealing the harsh realities of mafia life. It offers a realistic and surprisingly glamorous look inside the criminal world, told from the perspective of someone who lived it.

‘Bonnie and Clyde’ (1967)

Arthur Penn’s film about Bonnie and Clyde, the famous bank robbers from the Depression era, is a classic. Starring Warren Beatty and Faye Dunaway as the couple, the movie follows their journey across the American heartland as they try to escape the police. It was groundbreaking for its time, mixing violence, love, and comedy in a new way. Rather than showing Bonnie and Clyde as simply dangerous criminals, the film presents them as rebellious heroes. The movie’s depiction of their dramatic and violent deaths was particularly innovative and had a lasting impact on filmmaking.

‘Catch Me If You Can’ (2002)

Steven Spielberg’s film tells the surprisingly fun story of Frank Abagnale Jr., a teenager who became a master con artist. Leonardo DiCaprio stars as Abagnale, who cleverly poses as a pilot, doctor, and more, all while cashing millions of dollars in forged checks. Tom Hanks plays the FBI agent relentlessly chasing him around the world. The movie focuses on Abagnale’s charisma and smarts, portraying his crimes less as serious offenses and more as a stylish and exciting journey of growing up.

‘American Gangster’ (2007)

Denzel Washington delivers a compelling performance as Frank Lucas, a heroin smuggler operating in Harlem, portraying him with a surprising sense of honor. The film, directed by Ridley Scott, is a dramatized version of the true story of how Lucas brought drugs into the U.S. using planes returning from the Vietnam War. It contrasts Lucas’s organized and disciplined operation with the corruption within the police force trying to stop him. Despite the harm caused by his actions, the film shows Lucas as a devoted family man and a pillar of his community. It also subtly compares his criminal business to the world of legitimate big business.

‘Blow’ (2001)

This film, starring Johnny Depp as George Jung, tells the true story of how one man helped create the American cocaine trade in the 1970s. It follows Jung’s life, from selling small amounts of marijuana to becoming involved with the powerful Medellin Cartel. The movie particularly focuses on his relationships and his wish to support his daughter, portraying him as someone shaped by bad luck and betrayal, rather than a ruthless criminal. It also shows a nostalgic view of his earlier, more carefree days before he was eventually imprisoned for a long time.

‘Public Enemies’ (2009)

Michael Mann’s film is a visually striking take on the life of John Dillinger, the famous bank robber. Johnny Depp portrays Dillinger as a surprisingly calm figure, emphasizing his image as a folk hero during the Great Depression. The movie centers on Dillinger’s daring escapes and robberies, alongside the FBI’s efforts to update their crime-fighting techniques to stop him. It presents Dillinger as a man of principle, contrasting him with the more self-serving agents pursuing him. The film’s style beautifully captures the look and feel of the era, and the action sequences are thrilling.

‘War Dogs’ (2016)

This darkly funny movie tells the story of two young guys who unexpectedly land a huge deal with the Pentagon to supply weapons to allies in Afghanistan. Starring Jonah Hill and Miles Teller, the film follows Efraim Diveroli and David Packouz as they get caught up in the risky business of international arms dealing. It shows how a flawed government system allowed them to succeed, portraying them as unlikely entrepreneurs taking advantage of the situation for their own benefit. The movie centers on their quick rise to wealth and the wild experiences that come with it.

‘Pain & Gain’ (2013)

Directed by Michael Bay, this action comedy is based on the real story of a group of bodybuilders in Miami known as the Sun Gym gang. Mark Wahlberg and Dwayne Johnson star as two of these men who resort to kidnapping and extortion in their attempt to get rich. The film uses bright, over-the-top visuals to highlight how ridiculous and excessive their crimes are. While what they did was serious, the movie portrays the characters as clumsy and foolish. It’s a satire that uses violent humor to poke fun at the obsession with money and achieving the perfect physique.

‘Monster’ (2003)

Charlize Theron gives an incredible and moving performance as Aileen Wuornos, a serial killer, in this crime drama. The film delves into Wuornos’ difficult life and the events that led to her killing seven men in Florida. Director Patty Jenkins focuses the story on her relationship with Selby Wall and the abuse she suffered. Instead of portraying Wuornos as simply a monster, the film aims to create empathy by highlighting her desperation and mental health struggles, rather than just the violence she committed.

‘Bronson’ (2008)

Tom Hardy plays Michael Peterson, who transforms himself into the notorious Charles Bronson, Britain’s most violent inmate. Director Nicolas Winding Refn crafts the film as a dramatic and artistic exploration of a man who sees fighting as a form of expression. The movie uniquely allows Bronson to tell his own story directly to viewers, breaking the traditional barrier between performer and audience. He’s portrayed as someone who craves attention and achieves it through wild behavior and imprisonment. The film’s over-the-top violence and theatrical style turn his aggression into a bizarre spectacle.

‘Chopper’ (2000)

Eric Bana became well-known worldwide for his role as Mark “Chopper” Read, an Australian criminal. The film is based on Read’s own writings from prison and combines dark comedy with shocking violence to show his troubled personality and captivating charm. The movie portrays Read as a notorious figure in the criminal world who exaggerates stories to create a larger-than-life image of himself. While it doesn’t ignore his violent acts, the film presents him as a fascinating character and storyteller.

‘The Iceman’ (2012)

Michael Shannon portrays Richard Kuklinski, a dangerous hitman who secretly lived a normal life as a husband and father. The movie delves into the contrast between these two sides of his life, showing how he balanced committing murders for the mafia with trying to keep his family safe from the truth. Shannon’s performance is unsettlingly calm, making Kuklinski a frightening yet surprisingly relatable character. The story centers on the immense stress of keeping his criminal activities hidden and examines the mental strain of his work, without simply labeling him as a villain.

‘Black Mass’ (2015)

As a movie fan, I was really struck by Johnny Depp’s transformation in this film. It tells the story of Whitey Bulger and his gang in South Boston, but it’s more than just a gangster movie. It really dives into the messed-up relationship between the FBI and the Irish mob, showing how Bulger, a seriously ruthless guy, played the system. He basically manipulated his FBI contact to take out his rivals. The film doesn’t shy away from showing his power in the community, and honestly, it’s terrifying how easily he gets away with things for so long. It’s a bleak look at how corruption can let a criminal like him thrive with no consequences.

‘Casino’ (1995)

Robert De Niro plays Sam “Ace” Rothstein, a character inspired by real-life gambling expert Frank Rosenthal. The film shows how organized crime ran Las Vegas casinos in the 1970s and how that control eventually faded. Director Martin Scorsese pays close attention to the details of how the mob stole money from the casinos and the unstable relationships between the people involved. Rothstein is shown as a very careful and organized man whose world is constantly threatened by chaos around him. The movie is a look back at the exciting early days of Las Vegas, before it became dominated by big corporations.

‘Donnie Brasco’ (1997)

Al Pacino and Johnny Depp star in this film about an unlikely friendship. Pacino plays Lefty Ruggiero, an aging mobster, while Depp is Joe Pistone, the FBI agent who goes undercover to bring him down. The movie isn’t just about the investigation, but about the genuine bond that forms between the two men, and the emotional toll of the deception. It shows a more human side to the often-overlooked, lower-ranking members of the mafia, portraying their struggles and the sacrifices they make.

‘Lord of War’ (2005)

Nicolas Cage stars as Yuri Orlov, a character inspired by notorious arms dealer Viktor Bout. The film shows how Orlov goes from selling a few guns to becoming a key weapon supplier for leaders and fighters around the world. Through Orlov’s cynical narration, the movie explores how he justifies his role in global conflicts. It also reveals the double standards of world governments, which often use private individuals to move weapons, and portrays the arms trade as an unfortunate but unavoidable part of a dangerous world.

‘Molly’s Game’ (2017)

Molly Bloom, played by Jessica Chastain, ran a secret, high-stakes poker game frequented by celebrities and powerful figures. The film, written and directed by Aaron Sorkin and based on Bloom’s own story, highlights her sharp mind and business skills as she built this exclusive world. It shows how she took control of her life after a skiing accident ended her athletic career. A key part of the story is Bloom’s decision to stay silent and protect those who played in her games, even when facing legal trouble.

‘I, Tonya’ (2017)

This movie, produced by and starring Margot Robbie, tells the story of figure skater Tonya Harding in a mockumentary style. It looks back at the notorious 1994 attack on Nancy Kerrigan, but from Harding’s point of view and through the eyes of the people around her – even those who aren’t entirely trustworthy. The film playfully challenges how the media reported the event, and portrays Harding as someone who faced hardship due to her background and a difficult home life, and who struggled against the system. It finds both funny and heartbreaking moments in this famous sports scandal.

‘American Made’ (2017)

Tom Cruise plays Barry Seal, a pilot for TWA who unexpectedly becomes a drug smuggler and then a secret informant for the CIA. The movie uses humor to tell the story of the Iran-Contra affair and how the Medellin Cartel grew. Seal is portrayed as someone who takes risks and quickly finds himself in a complicated situation, trying to play every angle. The film highlights the ridiculousness of his life, especially when he’s overwhelmed with money. Ultimately, it presents illegal government actions as a messy and accidental series of mistakes.

Tell us which of these criminal portrayals you found most compelling in the comments.

2025-11-26 12:18