John Cusack And Jeremy Piven: The Evolution Of Their Relationship From Friends To Foes

Much like Hollywood marriages, Hollywood friendships are often put to the test by fame, success, and competition. That seemed to be the case for John Cusack and Jeremy Piven, longtime best friends from the Chicago suburbs who were dedicated to their craft and rose through the ranks of Hollywood together in a proto-Ben Affleck and Matt Damon relationship, regularly teaming up on projects. Cusack found success early, landing leading man roles regularly but always willing to bring Piven along for the ride. Piven was no slouch in the talent department, but he seemed relegated to character actor and supporting status while his pal's star shone.

That seemed to change when Piven landed his true breakout role in "Entourage" as the bombastic talent agent Ari Gold. Piven had worked steadily since the '80s, as had Cusack, but now his was the name in the headlines. And it was one of those headlines that appeared to be the nail in the coffin for the once dynamic duo from Chicago, containing a mention of jealousy, or at least a lack of support, that drove a firm wedge between the childhood friends.

John Cusack and Jeremy Piven were pals from their early days, growing up in the Chicago suburbs together. They attended elementary and high school together, and Cusack and his fellow megastar siblings all attended the Piven Theater Workshop, taught by Piven's parents, Byrne and Joyce Piven. After high school, the pair went to New York University together and shared an apartment before returning to Chicago and starting a theater company together. 

While promoting the movie "Serendipity," in which Cusack and Piven played best friends, Piven told The Orlando Sentinel, "I've known the guy since we were 8 years old. We might as well play best friends in a movie. If we can't do that well, we should both get into roofing." He continued, "I'm not in a relationship, now. But Johnny and I are kindred spirits, maybe even soulmates. Who knows? Maybe a friend can be that for you. It's a lot like a love affair. I don't even know if I can articulate it. We've had a theater company together since 1988, and we love hanging out together and working together. We make each other laugh."

John Cusack and Jeremy Piven pursued acting together, beginning their careers within a few years of each other. Cusack's first feature film was the 1983 comedy "Class," also starring his sister Joan Cusack and their father, Dick Cusack. Piven's feature film debut was in the 1986 film "Lucas."

Together, Cusack and Piven starred together in nine films, beginning with the comedy "One Crazy Summer," in which Cusack played the lead and Piven played a supporting role. Other films included "Say Anything..." "The Grifters," "The Player," "Bob Roberts," "Floundering," "Grosse Pointe Blank," "Serendipity," and "Runaway Jury." Speaking about their work in "Serendipity" together, one of the films where they share the most screen time as Cusack chases the stunning Kate Beckinsale, Piven told The Chicago Tribune, "If you could make your best friend believe you when you're acting, you're onto something."

Though they started their careers around the same time, John Cusack's star rose faster than Jeremy Piven's. Cusack was frequently cast as the leading man, albeit a quieter, quirkier, and more introspective one, while Piven often played second fiddle further down the call sheet. The Orlando Sentinel directly asked about Cusack "helping" Piven get into movies with him, while noting that Piven is often capable of upstaging him comedically. Piven attributed it to merit, replying, "I think we're both hams ... Our policy is the same as with our theater company. No one is handed a role in the theater company. Whoever has the clearest vision, the sharpest take, gets it," adding, "He's so good, you'll never steal a scene from him. But if you can? Take it!"

But Piven did express some ever-so-slight frustration at his sidekick status. "I'm over 40 movies into this, and I've played more best friends than friends I actually have. Maybe it is time I stopped apprenticing and tried to carry a movie. If somebody will let me," he told the outlet.

In "Serendipity," John Cusack and Jeremy Piven play best friends on-screen, mirroring their real-life relationship. Speaking with The Chicago Tribune while promoting the film, Piven said, "Johnny and I, we're simpatico, we're brothers from another mother, we grew up together. All I had to do is look at the guy. I didn't have to invent anything." He continued, "Your best friend is playing your best friend. You're giving a speech about your best friend. I mean, if there's anything my parents have taught me is just get out of your own way and be."

Cusack, offering a rare insight into his personal life, also spoke about Piven with the outlet. "We've done a lot of theater together, so it's very easy and very fun to work with people who have a shorthand with you. So whenever I work with Jeremy or my sister Joan [Cusack], it's always kind of effortless and really fun."

As jovial as he appeared in interviews around the time of "Serendipity," the cracks in Jeremy Piven and John Cusack's relationship were starting to show, at least when it came to Piven's point of view. Throughout his interviews at the time, it seemed he was ready to break away from the role of the "sidekick." "I just thought I don't know if I can play this guy again," Piven told The Chicago Tribune. "I did it with so many great people. I did it with Johnny in 'Grosse Pointe Blank,' I did it with Nic Cage in 'Family Man.' Do I want to go down this road again?"

He noted further into the interview, Piven said, "I've been apprenticing the job now for over 40 movies, and I've been studying since I was 8. And I feel like Johnny does such a great job at it, and I've been right there with him for so much of it. So I see how it can be done right." Piven put it more bluntly during an appearance on "The Daily Show," (via ABC) declaring, "If I have to see another guy get the girl again, I'll implode."

Jeremy Piven had dozens of film and TV credits to his name and was well respected as a supporting actor (with the occasional leading role), but he seemed firmly locked in the second-place position. That is until he landed the role of Ari Gold in HBO's "Entourage" in 2004. Ari Gold was loud and loquacious, prone to wordy fits of rage and clever insults, while still dedicated to his client, Vinnie Chase (Adrian Grenier, whose own life looks different now that he lives on a farm) and beloved family. Piven earned four Primetime Emmy nominations and won three in the supporting actor category for "Entourage," but he was and remains one of the more successful members of the cast.

Looking back on the series, Piven admitted he was surprised at the breakthrough, telling Vanity Fair, "I've always been an underdog, and I don't know any other way to think. You know, I was 40 movies into it before we even started 'Entourage.' As an actor you are used to rejection, you develop a thick skin, so to have this kind of success ... was not expected in any way, shape, or form."

Piven admitted the intense energy required to play Ari Gold took a slight toll on him. "Everything means the world to him. And so it was just so fun and cathartic to play that. And at the same time  ... listen, your body thinks you're throwing a temper tantrum for 12, 14 hours a day. So it can be a little taxing. It's been a very welcome break," he told the outlet.

As Jeremy Piven was riding high on the success of "Entourage," it seems his eclipsing of John Cusack's star, however slight or temporary, was the beginning of a serious rift between the two. When asked by Best Life in 2007 at the height of his "Entourage" success how Cusack felt about it, Piven said, "No comment. I mean, you could fill in the blank, I bet." He added of Cusack, as noted by The Washington Post, "I was always proud of him, and I was always in his corner."

"It just says so much about a person if he has space for other people's success," Piven 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."

Cusack refuted a rift immediately, telling People in a statement at the time, "It's quite the contrary. I am very happy for Jeremy. I wish him the best and I always have." But the damage to the relationship appeared to have been permanent.

Jeremy Piven and John Cusack's last project together was "Runaway Jury" in 2003, a moderately well-reviewed but more or less forgotten legal thriller. The next year, Piven blew up with "Entourage." Cusack's career wasn't anything to scoff at at the time, and he continued landing roles in films like "1408," "Must Love Dogs," "2012," and "Love & Mercy." However, his career prospects slowly started to dwindle with more direct-to-video releases and less prestigious or successful box office parts. After his success on "Entourage," Piven went on to another TV role with the historical drama "Mr. Selfridge," but his career similarly started to run dry.

Both actors have had rocky reputations in their later Hollywood years. Piven faced assault allegations in 2017 and 2018 from multiple women, some dating to 1985. He denied all the allegations and told KTLA's Frank Buckley on the "Frank Buckley Interviews" podcast in 2023 that he had "nothing to hide" and ended up embracing his retreat from the spotlight. There was also his infamous claim of suffering mercury poisoning from sushi, which caused him to miss several performances of a play, which some took as a sign of general erratic behavior.

Cusack, meanwhile, has continued steadily working, but Hollywood won't cast him as much anymore. This can perhaps be tied to his expressing an intense dislike for Hollywood and its machinations. As he told The Guardian in 2014, "It's a wh***house and people go mad." Cusack has also had some unverified reports of being difficult to work with, though no one has come forward with a formal complaint.

After the Best of Life interview, neither John Cusack nor Jeremy Piven made much mention of each other in interviews, so the state of their once-powerful friendship is a bit of a mystery. There are signs tensions have cooled in comments they've both made. In a 2014 Reddit Ask Me Anything session, Cusack said it was "nothing but love" between them but would not elaborate further.

A year later, an interview with The Guardian asked Piven directly if he and Cusack were friends again. "You know, it's interesting, because we met when we were kids at my parents' theater and my parents were doing 'The Seagull.' We took turns playing the child and we were friends ever since. And Joan [Cusack] is such an angel. I have a lot of history with the Cusacks." When pressed on the fact that he didn't answer the question, Piven offered, "Well yeah, absolutely! Once you have such history with someone, then yeah. I think we were all lucky to find each other."

Cusack and Piven remained quiet on each other for quite some time afterward. The first mention of their former friendship in over a decade came in a 2025 Aish interview with Piven about his film "The Performance." He again mentioned alternating with Cusack in his parents' production of "The Seagull," but nothing more.

Cusack has yet to make any further as he's grown more reluctant to grant interviews in recent years. He made a rare comment at the 2026 San Diego Comic Con about his pivot away from leading man to graphic novelist, telling Variety he was pleased there was "no committee" compared to putting together a Hollywood film.