“It's been a crazy couple of weeks,” Anthony Ippolito tells me. The star of the upcoming Sylvester Stallone biopic, I Play Rocky, is at the airport traveling from Saturday night’s Academy Museum Gala in Los Angeles to Monday’s night debut of I Play Rocky in Rome. Over our phone call, you can hear travelers wrangling their kids and flight attendants calling for Zone 3 passengers to head to their gate. But the hectic airport experience is exciting for Ippolito. “I've never been to Italy,” the son of two Italian parents from Long Island says. “It's crazy that it's taken this long, but at least it's happening.”
Something very similar could be said about Ippolito’s journey from a child actor in commercials to his role as the Italian Stallion in I Play Rocky—out in theaters on November 6. After appearing in the Netflix teen drama Grand Army with Odessa A'zion (Marty Supreme), the actor moved on from roles like “Blowdried Jock” and “Boy on Subway” to land a part in Paramount+’s The Offer, which followed the making of The Godfather (Ippolito played Al Pacino in the biographical miniseries).
But now the actor’s taking on Stallone, making appearances alongside today’s biggest actors at Academy Museum of Motion Pictures events—and doing it in style. For the Academy Museum Gala, he was decked out in a Giorgio Armani shawl-collar dinner jacket and trousers, and smoking scarf, all black. Ippolito thought the addition of the scarf was an especially nice finishing touch. “Yeah, I was a big fan,” he says.
Ippolito in his full Giorgio Armani look for the Academy Museum Gala.
“I like to try to feel comfortable, especially because this is so new,” Ippolito tells me. “A lot of these events, it’s hard to walk a line between making a statement and having it still feel like it's an extension of you.”
Luckily, Armani’s looser suit is perfect when you’re meeting fellow actors that you’ve admired your whole life and you’re sweating bullets. “That's the other thing,” Ippolito says of the breathable look. “I saw some incredible fits last night, but when you take into account the fabrics ... there wasn't very much air conditioning there.”
Before he jets off to Rome, Ippolito shares more with Esquire about working with Armani, why he wanted to play Stallone, and how he had to live out his own underdog story just to land the role.
On His Giorgi Armani Look for the Academy Museum Gala
“I’ve always been a huge fan of ’80s and ’90s Armani. They have a lot of relaxed fits. Loose. It's very comfortable. It doesn't feel incongruent to what you feel like you want to express. At one point it was supposed to be a white blazer and then I changed my mind at the last second. But I just wanted to feel comfortable even though it was an event with a lot of cool people.”
“I’ve always been a huge fan of ’80s and ’90s Armani ... I just wanted to feel comfortable even though it was an event with a lot of cool people.”
On Meeting Andrew Garfield
“It was an incredible room. Coleman Domingo gave an incredible speech, and seeing John Carpenter was very cool. Andrew Garfield actually approached me and said he was excited to see the film. I couldn’t believe it. I was shocked. Just very, very surreal. It's kind of like you're dreaming a little bit in these moments, because I told him—and it's true of so many of the people there last night—that I've looked up to his work for so many years. You never really think you're going to be able to say that to him and then have a moment where he's actually seen some of my stuff.”
“Just very, very surreal,” Ippolito says of meeting stars like Andrew Garfield. “It’s kind of like you’re dreaming a little bit in these moments.”
On Going from Playing Al Pacino to Playing Sylvester Stallone. Who’s Next, De Niro?
“I think if something fictional happens to come up, I wouldn't shy away from it at this point. It's been a pleasure to be able to do this, but there's a lot of responsibility and weight. The Offer was an incredible experience and I had the pleasure of meeting Pacino. Thankfully, he saw the show and had a positive response. But with Stallone, they're vastly different people and had incredibly different careers. It was an honor to be in the situation, to play both of them, but I'm also excited to explore some fictional circumstances as well.”
“I think if something fictional happens to come up, I wouldn’t shy away from it at this point.”
On Landing the Part
“Nobody was asking me to audition for this, which made it a little awkward. I read an article that Peter Farrelly was doing this movie and I just thought, I'd love to try to get in a conversation for that. I sent in a tape that I recorded in my grandmother’s basement, because it was very much stuck in the ’70s and just felt period correct. Then, when I got my hands on the script, I devoured it and sent another tape. You feel sometimes like you're sending your stuff into an abyss, especially when nobody's asking for the thing in the first place. Thankfully, I eventually heard that they were interested in talking more.”
“The raw eggs? Yeah, I did it once by myself and then once on set. I definitely did some interesting stuff.”
On ... Eating Raw Eggs
“The raw eggs? Yeah, I did it once by myself and then once on set. I definitely did some interesting stuff. Plus, it was actually pretty funny: When we filmed at the Art Museum in Philadelphia, they actually had to move the Rocky statue the day that we were shooting on the steps.”
On His Hopes for I Play Rocky
“I just hope that the film resonates with people. Rocky was so impactful because it's the underdog story, and this kind of angle is very much true to his real life. This is what he went through, and it’s pretty remarkable.”