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Home Featured Story

‘I Play Rocky’ Casting Director Rick Montgomery Says The Actors Who Really Wanted These Roles ‘Went the Extra Mile’

Megan McLachlan by Megan McLachlan
November 12, 2026
in Featured Story, Film, Interviews
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Anthony Ippolito and Stephan James in the gym, part of I Play Rocky casting

CR: Amazon Studios

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Casting director Rick Montgomery talks to The Contending about putting together the ragtag team of comedic and dramatic character actors for I Play Rocky. 

Casting director Rick Montgomery has worked with director Peter Farrelly of the Farrelly Brothers for more than 30 years. So when Peter starting doing more dramatic films, Montgomery was ready. 

“Oh, it was extremely natural,” said Montgomery. “Because even like Green Book, Pete’s really doing dramedies. So it’s the drama of the picture itself, which Green Book certainly was, as well as the drama in I Play Rocky. But then the comedic elements are what we love. So we like to go to the movie and start laughing. And then all of a sudden we’re crying. And then we’re holding on to hope. And, oh, my gosh, this has to happen. And, oh, no, don’t do that. And just to have those swings of emotion while watching a movie is so fantastic.”

So is I Play Rocky a comedy. . .or a drama? (The Golden Globes would say it’s a comedy!)

“That’s a producerial sort of question,” he laughed. when it comes to. That’s not my department, so I don’t have to worry about it. There are dramatic moments in the film, no question. But it feels more like a comedy that you really feel good about it when you’re all said and done.”

Finding the I Play Rocky Cast

“Everybody, the people who really wanted the job, they went the extra mile,” said Montgomery on finding the film’s cast. “They really did put themselves out there. You know, you put yourself on tape for a role.”

By now, most people know the story of how Anthony Ippolito came to secure the role (he self-taped from his grandmother’s basement), but he wasn’t the only one who really wanted to be part of the project. 

“I got a call from Stephan’s (James) manager who said, ‘Hey, what about Stephan?’ And it’s like, ‘Are you kidding me? Of course.’ I didn’t think he would even want to do something like this or a smaller role in a picture. But he was really into it.”

AnnaSophia Robb was also really into playing Sasha, Stallone’s long-suffering wife. The I Play Rocky team selected four women around the same age for the part and invited them to read. Montgomery said they even opened it up so the women could talk to him or Pete before the read. 

“AnnaSophia took advantage of it and she called me and she had stuff she had already worked out in her head and was working on. And so she asked me not questions like, what’s the director looking for? It wasn’t things like that. She was asking me about the character so she could develop her character. The character of Sasha in such a deeper way. So she decided she wanted to read, too. And so she did it, and she was amazing. She was innocent. She was the rock in Gibraltar. All these qualities in her.”

“We Like to Use People We’ve Used Before”

Montgomery also was finally able to find a project for Toby Kebbell, an actor both he and Farrelly had been wanting to work with for a while. 

“Having worked with Pete as long as I have, I know these things. And many times, it’s easy to remember because I like the actor so much myself. Toby is someone I’ve always been fond of. I just think he’s an amazing actor. And he showed his true stripes in this. And the whole idea that I could get a guy to play it somewhat the straight man and then P.J. to do the comic relief. It’s an old vaudeville routine, the straight guy and the jokester.”

Plus, because Farrelly has a rolodex of actors he likes to work with, that made it easy to find Stallone’s father: Matt Dillon. 

“I went to Pete and said, I think Matt would be perfect for this. And Pete said, ‘Oh my God, yes, I agree.’ Yeah, let’s get Matt because we both love Matt. We want Matt, you know, and we love to put people in the same movies. We like to use people we’ve used before.”

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Megan McLachlan

Megan McLachlan

Megan McLachlan is a co-founder of The Contending who lives in Pittsburgh, PA. Her work has appeared in Buzzfeed, Cosmopolitan, The Cut, Paste, the Pittsburgh Post-Gazette, Thrillist, and The Washington Post.

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