The allure of the outlaw lifestyle has always been intriguing to audiences. They are entertaining stories that contain sex, violence, and thematically rich stories of morality, containing the consequences of criminal activity while providing insight into the human condition. Directors like Brian De Palma and Martin Scorsese have taken the genre and lifted it to its heights, giving gangster movies a home in people's hearts.

A perfect gangster movie has compelling characters with complex motivations, a well-paced plot filled with tension, authentic dialogue, and a vivid portrayal of the setting and era, thus giving audiences a new perspective on history and how the world works. In the last ten years, gangster films have experienced something of a resurgence, and while most are quite good, only a few are worthy of standing next to the all-time greats.

13 'The Highwaymen' (2019)

Directed by John Lee Hancock

This is the familiar story of bank robbers and gang affiliates Bonnie Parker and Clyde Barrow, but told from the perspective of the lawmen tracking them. Kevin Costner, Woody Harrelsion and Kathy Lee Bates star in John Lee Hancock's well-appointed perid crime thriller for Netflix.

The Highwaymen is a well-crafted and exceedingly well-acted procedural with one hindrance of note that isn't even the movie's fault: there's no way a movie about the lawmen tracking Bonnie and Clyde was ever going to be as thrilling as a movie about Bonnie and Clyde, especially in the shadow of the New Hollywood classic film. Still, it's easy ro recommend The Highwaymen based on the lead performances alone.

12 'The Many Saints of Newark' (2021)

Directed by Alan Taylor

Released day-and-date in theaters and on HBO Max (now Max), Alan Taylor's The Many Saints of Newark is a prequel to one of the most iconic shows of all time, HBO's The Sopranos. Alessandro Nivola and Michael Gandolfini, it chronicles the rise of Anthony Soprano in the 1960s, specifically against the backdrop of the 1967 riots.

The Many Saints of Newark certainly isn't on the same level of the series that inspired it, but if anything it's a little underrated. The most remarkable part of the enterprise is the performance of Michael Gandolfini, who bears an incredible likeness to late father James Gandolfini. Despite receiving generally positive reviews, The Many Saints of Newark was unfortunately a box-office bomb.

11 'The Gentlemen' (2019)

Directed by Guy Ritchie

Before the popular Netflix series of the same name, there was Guy Ritchie's 2019 movie of the same name, generally well-reviewed by fans and celebrated as a return to form. Matthew McConaughey, Charlie Hunnam and Colin Farrell star in a fun, suave comedic thriller about warring gangsters feuding over a marijuana empire in London.

In addition to receiving overall warm reviews from critics, The Gentlemen was released just in the nick of time to have a shot at box-office success before peak pandemic era challenged theaters. Released stateside in January 2020, the film grossed a respectable $115 million, over five times its reported budget. The spinoff TV series premiered earlier this year to positive critical notices and high audience interest.

10 ‘The Drop’ (2014)

Directed by Michaël R. Roskam

In James Gandolfini's final role, he plays Marv, the owner of a bar that acts as a “drop” location for illegal cash transactions from the local mobsters and criminals. But when the bar is robbed, the bartender, Bob (Tom Hardy), finds himself caught up in a web of conspiracy. The aggressors make Bob confront his past and keep him guessing as he tries to make the best decisions to protect himself and his family.

The narrative makes this movie excel, filling it with meticulous twists and turns from the moment the bar is robbed to when audiences learn of secret identities and the motives of innocuous characters. Keeping a slow-burning pace that allows for gradual reveals and simmering conflicts to come to a head, The Drop adds depth and suspense to the story, which helps the viewers stay engaged until the final payoff.

Rent on Apple

9 ‘The Infiltrator’ (2016)

Directed by Brad Furman

The Infiltrator is based on Robert Mazur's autobiography and stars Bryan Cranston as Mazur, a U.S. Customs special agent. Set in the 80s, when the war on drugs was reaching its height, the film sees Mazur going undercover as a money launderer to infiltrate the drug trafficking network of Colombian drug lord Pablo Escobar.

Cranston's performance carries this movie, portraying Mazur with gripping authenticity as he remains morally conflicted by the actions he has to take. Surrounded by the suspenseful atmosphere in the world of drug trafficking, The Infiltrator keeps viewers on the edge of their seats and immersed in the possibilities that could happen. Cranston creates empathy with this character, giving a different relationship with the viewer that other gangster films don't have.

8 ‘Wrath of Man’ (2021)

Directed by Guy Ritchie

Based on the 2004 French film Cash Truck, Wrath of Man stars Jason Statham as H, a mysterious and skilled security guard hired by an armored truck company in Los Angeles. H’s background is shrouded in secrecy as he proves himself to be a formidable protector of the company’s cash shipments. Eventually, he becomes embroiled in a deadly game of revenge and uncovers the truth behind a heist that resulted in his son's death.

Wrath of Man takes on vengeance with intense gusto, showcasing Guy Ritchie’s signature style of gritty and fast-paced violence. However, it may fall short for some viewers looking for character development, as supporting characters are underdeveloped, and H’s motivations are not fully fleshed out. Nevertheless, this seems more of a creative choice, and plenty of excitement happens elsewhere, seeking deeper storytelling and character exploration through fight choreography and H's rage.

7 ‘Legend’ (2015)

Directed by Brian Helgeland

This fascinating gangster picture stars Tom Hardy in a dual role as twins Ronald and Reginald Kray, notorious gangsters in London’s East End during the 50s and 60s. The film shows their criminal empire and how they controlled nightclubs, gambling rings, and extortion rackets while rubbing shoulders with celebrities and other politicians.

Legend maintains the dark allure of a stereotypical organized crime film while delving into the Kray brothers' complex relationship and the impact their criminal activities had on those around them. Offering a stylish portrait of London’s underworld, Legend is bolstered by Hardy’s performance, who has to possess contrasting personalities and motivations.

Rent on Apple

6 ‘The Outfit’ (2022)

Directed by Graham Moore

Set in the world of organized crime, The Outfit follows an expert tailor (Mark Rylance) who runs a bespoke suit shop in Chicago. When Leonard becomes entangled in a dangerous situation involving a mysterious woman and a violent gangster, he must use all of his cunning skills to navigate the treacherous underworld and protect himself and his business.

The Outfit explores themes of loyalty, betrayal, and survival as the protagonist finds himself caught in a deadly game of cat and mouse where nothing is what it seems. With an intense atmosphere, The Outfit is a thrilling take on a classic genre that soars where others fall. The plot inevitably allows the audience to relate to Rylance's character because he is in a situation that could have happened to anyone in the wrong place at the wrong time.

5 ‘The Gangster, The Cop, The Devil’ (2019)

Directed by Won-Tae Lee

The South Korean action thriller The Gangster, The Cop, The Devil is an unlikely partnership between a hardened gangster and a determined police detective teaming up to track a vicious serial killer targeting gang members. When a gangster survives his attacker, he forms an uneasy alliance to seek revenge, leading to an exploration of the blurred lines between good and evil as the trio confronts their demons while pursuing their common enemy.

The seamless blend of action, crime, and drama makes The Gangster, The Cop, The Devil one of the most refreshing gangster films to come out in a while. The unlikely alliance creates a compelling dynamic, driving the narrative forward with tension and intrigue that is sure to grip any fan of the genre. With Won-Tae Lee's tight pacing and fast-moving sequences, The Gangster, The Cop, The Devil will quickly become a new viewer's favorite.

4 ‘A Most Violent Year’ (2014)

Directed by J.C. Chandor

Set in New York City during the winter of 1981, A Most Violent Year follows Abel Morales (Oscar Isaac), a determined immigrant trying to grow his heating oil business while navigating the city's increasingly violent and corrupt environment. As Abel faces threats from rival competitors, violent hijackings, and an aggressive District Attorney, he must grapple with difficult choices when protecting his family and business.

Abel’s moral dilemmas are the tip of the iceberg. A Most Violent Year offers a nuanced portrayal of the city, capturing urban decay and the allure of the American Dream. With its compelling storyline, complex characters, thoughtful direction, and career-best performances from Isaac and Jessica Chastain, A Most Violent Year is a thrilling cinematic experience that raises the stakes with each act.

3 ‘Sicario’ (2015)

Directed by Denis Villeneuve

Sicario follows FBI agent Kate Macer (Emily Blunt), who is recruited by a government task force led by a mysterious operative. As she becomes increasingly involved in the task force operations, she finds herself in moral and ethical conflict with herself over the jobs she has to do. The film offers a tense portrayal of the brutality that goes on in the drug trade and the lengths to which individuals and governments will go to combat it.

Compelling and thought-provoking, Sicario portrays the power struggles within cartels operating along the U.S./Mexico border through a poignant narrative, striking cinematography, and career-best work from Emily Blunt. Delving into the inner workings of these organizations and depicting their tactics when fighting over territorial disputes, Sicario tells a gripping story that shows the complexities of the current war on drugs.

2 ‘Black Mass’ (2015)

Directed by Scott Cooper

Based on the book by Dick Lehr and Gerard O’Neill, Black Mass stars Johnny Depp as the notorious Boston gangster James “Whitey” Bulger. It chronicles his rise to power as the leader of the Winter Hill Gang and his alliances with the FBI as an informant. Throughout the film, audiences see Bulger's reign of terror over South Boston during the 70s and 80s, watching as his criminal empire becomes intertwined with law enforcement.

Depp’s transformation into the notorious gangster is mesmerizing, capturing both his charisma and ruthless brutality. Supporting characters, played by Benedict Cumberbatch and Joel Edgerton, add depth to the complex web of relationships and betrayals that are so pertinent to the story. Effectively blurring lines between law enforcement and criminality, Black Mass is an enthralling yet challenging experience throughout.

1 ‘The Irishman’ (2019)

Directed by Martin Scorsese

Spanning several decades, The Irishman follows the life of Frank Sheeran (Robert De Niro), a truck driver who becomes a hitman for the Bufalino crime family. It shows Sheeran’s involvement in organized crime and his close relationship with union leader Jimmy Hoffa (Al Pacino), offering a new take on key historical events like Hoffa’s disappearance.

Offering a meditation on morality and the passage of time, The Irishman soars under the direction of the king of the crime genre, Martin Scorsese, and stellar performances from its ensemble cast, including the long-awaited return of Joe Pesci. As a powerful exploration of the underworld and a reflection on the choices people make that shape the rest of their lives, The Irishman is a true cinematic epic that will continue to be one of the most remembered gangster films.