Andrea Ciriaco is a senior writer for Collider who is an expert in Hollywood history and all things Classic Movies.
For decades, audiences have been fascinated by the subject of organized crime and classic gangster films such as The Godfather, A Bronx Tale, and Goodfellas. Whether it's the rush of living vicariously through these mafiosos or unraveling their complex motivations, the gangster genre remains a timeless favorite among film fanatics.
9 Sonny Black - Michael Madsen 'Donnie Brasco' Michael Madsen portrays the hot-headed Sonny Black in Donnie Brasco, who is promoted to lead his crew after the boss of the family is gunned down. Black is a rather young choice to lead his crew and abides by the core rules of the mafia, but he eventually takes his new position of power to the extreme. After his new club is raided on opening day, he whacks anyone he slightly suspects of being a rat, leaving a long blood trail behind him.
7 Caesar "Rico" Bandello - Edward G. Robinson 'Little Caesar' Edward G. Robinson delivered his breakthrough performance in Little Caesar as Rico "Caesar' Bandello and essentially laid the foundation for all future mob bosses in cinema. Similar to most gangster films, Bandello starts out as a small-time criminal who advances through the ranks until he seizes the opportunity to take control of the organization, replacing the current boss, Sam Vettori .
It's not rare for a boss to infiltrate the authorities on some level, but it is rare for a boss to be an FBI informant, which Costello uses to his advantage. Much like Bulger, Costello tactfully abuses his protected status to further his illegal operations and successfully manages to keep this information secret from the rest of his crew.
His relationship with Amsterdam , brings out a rare quality in Cutting, but once he discovers Amsterdam's true identity, he reveals how coldblooded he truly can be to those who betray him. One physical attribute that sets Cutting apart from other bosses is his crystal blue glass eye that stares into one's soul, striking an unpredictable sense of fear in even the bravest of men.
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