For years, actor Jeremy Piven was best known for playing second banana to childhood friend John Cusack, accompanying him to roles in One Crazy Summer, Say Anything, Serendipity, and more movies. After Piven found bigger success on his own terms with his role in the mid-’00s series Entourage, their tag-team act, along with their friendship, came to an abrupt stop. Read on to find out why, according to Piven, the actors’ friendship soured for a time and to learn where they stand today.
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The actors’ relationship goes back to their shared childhood outside Chicago in Evanston, Illinois, where Piven’s parents, Byrne and Joyce Piven—both stage actors—founded the influential Piven Theatre Workshop. The drama school is known for producing a generation of actors, including Lili Taylor, Aidan Quinn, and Cusack, who began training there at age nine and was a member of its Young People’s Company, according to a 1985 article in The Chicago Tribune.
Piven, now 58, and Cusack, now 57, shared a child role in the workshop’s production of The Seagull, according to a 2015 interview with The Guardian. Along the way, they became friends, both graduating from Evanston Township High School in the early ’80s and later sharing an apartment.
“I’ve known the guy since we were eight years old,” Piven recalled to The Orlando Sentinel in 2001. “Johnny and I are kindred spirits, maybe even soulmates. We’ve had a theater company together since 1988, and we love hanging out together and working together. We make each other laugh.”
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Cusack started appearing in films while still a teenager, with small roles in early Brat Pack films including Class (1983) and Sixteen Candles (1984), followed shortly after by the starring role in Rob Reiner’s The Sure Thing in 1985. With the iconic boombox-holding role of Lloyd Dobler in 1989’s Say Anything, he soon transitioned from being a teen comedy bit player to a bonafide romantic lead and dramatic actor.
Meanwhile, Piven too left the Midwest for Hollywood. In addition to roles in Lucas and the frat farce PCU, he became known for frequently filling in the sidekick/best friend role in films including The Family Man. Piven was most often found in that slot next to Cusack. The friends appeared together in 10 films, including The Grifters and Grosse Pointe Blank.
For many years, bringing their natural chemistry to their onscreen roles appeared to suit them both well. “We might as well play best friends in a movie,” Piven told The Orlando Sentinel. “If we can’t do that well, we should both get into roofing.”
In 2004, Piven was cast in the role for which he’d become best known: abrasive Hollywood agent Ari Gold on HBO’s Entourage. The show, loosely based on the real life of executive producer Mark Wahlberg, ran for eight seasons and also spawned a TV movie. Piven won three Emmys for his work on the comedy.
But while the show brought more recognition and power to Piven, he’s said that it didn’t do any favors to his long-time friendship with Cusack. In a 2007 interview with the print edition of Best Life, the Mr. Selfridge star implied that it led to issues between the two. Asked how Cusack felt about his newfound super-stardom, Piven said, “No comment. I mean, you could fill in the blank, I bet.”
“It just says so much about a person if he has space for other people’s success,” he went on to say. “I have always been so proud of my friends’ success … You start getting into trouble in life when you start comparing and contrasting your life to anyone else’s. You don’t win when you do that.”
Following the publication of Piven’s interview, Cusack denied being jealous and said he felt nothing but happiness for his friend. “It’s quite the contrary,” he told People in a statement. “I am very happy for Jeremy. I wish him the best and I always have.”
In an “Ask Me Anything” in 2014, a Reddit user asked the High Fidelity actor, “What is the real story between Piven and you?” Cusack wrote, “Grew up together in chicago [sic]. Old friend…” Asked to address whether they were “still feuding,” the star replied, “no way man nothing but love.”
Still, the former frequent co-stars haven’t appeared together onscreen since 2003’s Runaway Jury. But Piven confirmed that they had mended things in his 2015 interview with The Guardian. “Well yeah, absolutely!” he replied when asked if the childhood buddies were friends again. “Once you have such history with someone, then yeah. I think we were all lucky to find each other.”
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