James Cagney as William "Rocky" Sullivan in Angels with Dirty Faces (1938)
Cagney is known for playing tough guys with an edge of pathos. In Angels, Cagney portrays gangster Rocky Sullivan. After getting out of jail, Rocky returns to his boyhood home. There he reunites with his former partner in crime, now a priest bent on reforming the neighborhood kids—who, unfortunately, admire the gangster.
Mickey Rooney as Lester "George Nelson" Gillis in Baby Face Nelson (1957)
Playing against type, Rooney shines as the cherubic but maniacal machine gun-wielding killer with a serious Napoleon complex. As part of John Dillinger's infamous band of outlaws, Nelson shows no remorse in killing anyone who gets in his way. Based on the true story of the smooth-faced killer who was public enemy number one in the 1930s.
Al Pacino as Tony Montana in Scarface (1983)
Pacino is Cuban refugee Montana, who reinterprets the American Dream by becoming a Miami drug lord, not through hard work, but through murder and mayhem. As his power rises, so does his drug addiction, paranoia and rage, which all lead to an inevitable bloody conclusion. A remake of the 1932 film.
Edward G. Robinson as Vincent Canelli in Black Tuesday (1954)
In this gem, Robinson plays an about-to-be-executed gangster who escapes prison with a fellow death-row inmate played by Peter Graves. The cops give chase as the duo tries to find money stashed by Graves before his encarceration. Robinson's wicked and utterly ruthless Canelli is a forerunner to the ultraviolent and amoral Mob characters of today's films.
Warren Beatty as Bugsy Siegel in Bugsy (1991)
Beatty portrays the notorious gangster in this film, which was nominated for 10 Academy Awards. The movie follows Siegel's attempts in the 1930s and '40s to create a gambling oasis in the Nevada desert. Today that oasis is Las Vegas. Beatty's future wife, Annette Bening, played mobster moll Virginia Hill in the
Robert Shaw as Doyle Lonnegan in The Sting (1973)
Gangsters have even appeared in comedies, such as this classic caper starring Robert Redford and Paul Newman as a pair of cons out to out-con Shaw's Mob boss as revenge for the death of a friend. Full of twists and turns and often-imitated scenes, the film won seven Academy Awards, including Best Picture.
Robert De Niro as David "Noodles" Aaronson and James Woods as Maximilian "Max" Bercovicz in Once Upon a Time in America (1984)
While most Mob movies deal with La Cosa Nostra, this Sergio Leone epic focuses on the rise and fall of a group of Jewish gangsters. We follow friends De Niro and Woods from their childhood in the gritty New York slums of the 1920s to their ascent during Prohibition and finally to their tragic "reunion" in the 1960s.
Ben Gazzara as Al Capone in Capone (1975)
Capone has been the subject of more movies than any other real-life mobster. Gazzara plays the legendary Chicago kingpin with a swagger and a thirst for vengeance in this mostly fictionalized account of Capone's life. Criticized for being too violent, it also features Sylvester Stallone in one of his first roles.
Al Pacino as Benjamin "Lefty" Ruggerio in Donnie Brasco (1997)
In this gritty drama based on a true story, Pacino gives yet another stellar performance, this time as a world-weary wise guy who mentors new "recruit" Donnie Brasco, played by Johnny Depp. An unlikely friendship blossoms between Depp and Pacino, even though the former is an undercover FBI agent trying to take down Pacino and his Mob cohorts.
Armand Assante as John Gotti in Gotti (1996)
As the head of the Gambino crime family, the late John Gotti was known as much for his crisp Italian suits as for his ruthlessness and rage. Assante portrays the Dapper Don in this HBO biopic pitting the violent crime boss against the FBI, which will do almost anything to take him down.
James Gandolfini as Tony Soprano in "The Sopranos"
Gandolfini portrays the complex, neurotic, womanizing and ruthless Tony Soprano in the operatic HBO series. The New Jersey crime boss has had numerous bloody battles with his late mother, uncle and nephew as well as with his somewhat dubious associates. But the misunderstood Soprano sincerely tries to do right by both of his families, which often results in tragedy.
Joe Pesci as Tommy De Vito in Goodfellas (1990)
Pesci's De Vito is utterly amoral and violent to a fault as he and fellow gangster Robert De Niro and new recruit Ray Liotta turn from petty crime to murder in order to rise up in the Mafia food chain. Based on a true story, Martin Scorsese's masterpiece is sometimes funny, often violent but always gripping. Pesci won the Best Supporting Actor Oscar.
Robert De Niro as Al Capone in The Untouchables (1987)
While not exactly a dead ringer for Capone, De Niro nevertheless makes viewers thoroughly believe he is the notorious capo in Brian De Palma's Oscar-winning film. De Niro relishes every moment on-screen as he thwarts Treasury agent Elliot Ness's (Kevin Costner's) attempts to bring him to justice in Prohibition-era Chicago.