The Sopranos

“I love watching him work”: Brad Pitt Managed to Convince His Favorite TV Star to Play a Gay Role That Would’ve Made Tony Soprano Enraged

James Gandolfini played a gay hitman in Brad Pitt's 2001 film The Mexican.


  • Brad Pitt managed to convince James Gandolfini to join the cast of The Mexican with Julia Roberts.
  • Gandolfini has played numerous roles as a mob guy, but in The Mexican, he was notably gay.
  • His character in The Sopranos was infamously known for being homophobic.

The passing of The Sopranos’ James Gandolfini in 2013 was a devastating time in the whole entertainment industry, but most especially for actor Brad Pitt. Having previously worked together in the past, it was such a huge loss for the Fight Club star.

brad pitt and julia roberts the mexican
Brad Pitt and Julia Roberts in The Mexican

Some of their works included 1993’s True Romance, 2001’s The Mexican, and 2012’s Killing Them Softly. In fact, Pitt was the reason Gandolfini got cast for one of his most iconic movie roles.

James Gandolfini Portrayed A Gay Hitman In Brad Pitt’s Movie

Brad Pitt and James Gandolfini co-starred in The Mexican, a dark comedy adventure crime film directed by Gore Verbinski. The script was originally intended to feature not-so-popular actors, but when Pitt and Julia Roberts came across the project, they decided to do it.

It was the actress who suggested Gandolfini to join the cast, but the Inglourious Basterds actor’s involvement convinced the Italian star to agree. In 2001, Pitt praised Gandolfini (via Entertainment Weekly):

He’s the man. He’s one of those great actors who finds meaning in every line. I love watching him work.”

Following the actor’s passing due to a heart attack in 2013, Brad Pitt paid his tribute:

I admire Jimmy as a ferocious actor, a gentle soul, and a genuinely funny man. I am fortunate to have sat across the table from him and am gutted by this loss. I wish his family strength and some semblance of peace.”

In an old interview via ABC News, Gandolfini talked about playing a mob guy for the nth time. He has famously portrayed Tony Soprano in HBO’s The Sopranos and Mickey Fallon in Killing Them Softly, but in The Mexican, he was notably a gay hitman. He confessed:

I have done it for 10 years. I had no more tricks. I couldn’t pull anything out of the hat for this kind of thing. He tortured me, tortured me, tortured me. Then I started thinking, ‘I’ve done a bunch of these guys, and this is kind of the final nail in the coffin. This is where you are at the end.’ So maybe if I played it that way in my mind, this is the last one, then it got interesting.”

Gandolfini was a staple in many classic crime movies, but his performance has always left a strong impression on the audience.

James Gandolfini’s Tony Soprano Revealed Why He Hates Gays

james gandolfini the sopranos
James Gandolfini in The Sopranos

While James Gandolfini’s role in The Mexican perfectly suited him, and the actor was quite satisfied with it, his character in The Sopranos would have detested it. Tony Soprano is infamously known for his hatred towards gay people. In one of the scenes where Tony talked about homos*xuality, he said (via YouTube):

He’s a f*g, now what am I supposed to do? In your circle, I’m sure you got all kinds of gays and trans, but not where I come from. I find it disgusting, men kissing men, holding hands in the streets, every f—king TV show now they rub your nose in it. Oh, no, don’t forget, I’m a strict Catholic. I agree with that Senator Sanatorium, who says if we let this stuff go too far, pretty soon we’ll be f—king dogs.”

Gandolfini probably had no issue playing gay roles, but it was quite surprising knowing his most iconic character was a massive homophobic.

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