The cast of Goodfellas did an excellent job at portraying some of the most notable gangsters in American history, and while it includes some big names like Joe Pesci and Robert De Niro, Goodfellas could have counted on the talents of Al Pacino, but he turned down the offer. Martin Scorsese has explored different genres throughout his career as a filmmaker, but he continues to be best known for his gangster movies, and the one often considered his best from the genre (and in general as well) is Goodfellas, released in 1990.

Based on the book Wiseguy, by Nicholas Pileggi (and with a script by him and Scorsese), Goodfellas chronicles the life of Henry Hill (Ray Liotta), from his days as a teenager running errands for Paul Cicero (Paul Sorvino) and his crew to his full involvement with the Lucchese crime family. While working for Paulie and company, Henry became close to some of the biggest names in the mob at the time, among those Tommy DeVito (Joe Pesci) and Jimmy “The Gent” Conway (Robert De Niro). Henry met Jimmy when he was still a teenager, and he was the one who gave him one of the most important life lessons: “never rat on your friends and always keep your mouth shut”.

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Jimmy was one of the most influential figures in Henry Hill’s life, and they even worked together dealing drugs behind Paulie’s back, but their friendship came to an end when Henry became an FBI informant and sent Paulie and Jimmy to jail. Jimmy was masterfully played by Robert De Niro, becoming one of his most memorable roles, but even though Scorsese and De Niro had already worked together many times before, Jimmy Conway wasn’t always a role for De Niro. The role of Jimmy Conway in Goodfellas was reportedly offered to Al Pacino first, and while he would have surely been outstanding in it, he turned it down.

Al Pacino reportedly turned down playing Jimmy Conway in Goodfellas in order to avoid being typecast in the gangster role. By the time Goodfellas was in production, Pacino was already known as an actor who played gangsters and did it phenomenally, this thanks to his performances as Michael Corleone in The Godfather and The Godfather Part II and Tony Montana in Scarface. While it’s understandable that Pacino rejected the offer to play Jimmy Conway to avoid keeping the “gangster” label, it seems strange that, the same year Goodfellas was released, he appeared in Warren Beatty’s crime comedy Dick Tracy, where he played a (comedic) gangster named Alphonse “Big Boy” Caprice”. Pacino has reportedly admitted he regretted this decision, but he was nominated for a variety of awards thanks to Caprice.

Even after Goodfellas and Dick Tracy, Pacino didn’t stay away from the gangster genre, appearing in Brian de Palma’s Carlito’s Way, Mike Newell’s Donnie Brasco, and he finally teamed up with Martin Scorsese (and Robert De Niro, ironically) in 2019 in The Irishman, where he played Jimmy Hoffa. Al Pacino playing Jimmy Conway in Goodfellas would have made the movie very different, but it’s hard to say if he would have been better than Robert De Niro, as they not only have different acting styles but also De Niro gave an excellent performance.

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