Get To Know John Cusack's Famous Friends & Collaborators

In 1985, a New York magazine article coined the term "Brat Pack," defining a group of young stars who appeared in various coming-of-age films together and seemed to be friends off-screen, too. The original Brat Pack included actors like Rob Lowe, Emilio Estevez, Judd Nelson, and even Tom Cruise, but it notably didn't include John Cusack, even though at that point he'd been in "Sixteen Candles" and acted opposite Lowe in "Class."

Instead, Cusack has forged his own path through Hollywood, not necessarily running as part of a pack but picking and choosing his friends and collaborators more carefully. The famously private star doesn't act nearly as much as he used to these days, but Cusack still keeps his friends close after decades in the industry. He learned that lesson early, telling The Guardian in 2020 that he felt like he'd lucked out early in his career to be guided by Rob Reiner. "Hollywood can be quite transactional and rough. I was lucky. I was 16, 17," he pointed out. "Rob would invite you into his home, look after you ... Movies were definitely the Wild West back then. But there were good people, too."

Cusack also isn't afraid to cut people off when the relationship is no longer working out. In addition to his close friends and collaborators, Cusack has also left a few people behind, falling out with friends while in the public eye. It must be tough to navigate, we imagine; read on to learn how Cusack has managed.

John Cusack and Tim Robbins first met on the set of "The Sure Thing," the Rob Reiner comedy that served as Cusack's first leading role. In it, he played a young man hitchhiking across the country on his way to Los Angeles, hoping to sleep with a girl who is, as the title suggests, a sure thing. One of the drivers who picks him up is played by Robbins, and Cusack said a fast friendship formed despite Robbins being 10 years his senior. In an interview with NPR, Cusack joked, "[H]e's a very deranged individual in a lot of ways, so we just got along great."

They starred in "Tapeheads" together shortly after "The Sure Thing" and went on to both act in "Cradle Will Rock," "High Fidelity," "Bob Roberts," "The Player," and more.

Cusack and Robbins reunited during an interview in 2026, discussing their longtime friendship at San Diego Comic-Con, where Cusack discussed his transformation from leading man to graphic novelist. They revealed that they'd been jointly fired from a project called "Straight to Hell" for refusing to shave their heads, but they'd already traveled to Spain for filming. "We got to hang out for like a week," Robbins gushed. "We went to the bullfights."

John Cusack grew up in Chicago, and when Hollywood came calling, he brought one of his high school buddies along for the ride. He's worked with Steve Pink many times over the years. In addition to their theater company and production company, Pink co-wrote and even directed several Cusack films. Their most recent collaboration was "Hot Tub Time Machine," but even earlier, Pink was by Cusack's side for "Grosse Pointe Blank" and "High Fidelity."

The former featured Cusack playing an assassin who returns to his high school reunion, and Pink told "SpitballingPod" that the idea came about because he used to help Cusack read scripts and choose roles. A lot of offers, he said, were based around Cusack holding a gun, playing cops or criminals. "If there's going to be a gun in your hand in a movie," Pink told his friend, "there should be a gun in your hand ironically." The politically minded friends devised a story that could comment on American culture that decade, and the rest was Hollywood history.

It's a mindset that served them well when they reunited in 2010 for "Hot Tub Time Machine." Though some audiences were surprised Cusack would do such a silly comedy, Pink defended his friend's choices to JoBlo, explaining, "John has always been able to deliver a darkly comic view of the world. He's always been good at trying to manage the insanity."

Steve Pink isn't the only high school friend that John Cusack worked with in Hollywood. In an interesting case of art imitating life, one of Cusack's earliest, best friends and biggest collaborators was Jeremy Piven, the actor who later broke out on the HBO hit "Entourage." Piven wasn't a hanger-on, though; he was an actor in his own right, and the two friends worked together many times in their early careers. They starred together in "One Crazy Summer," "Say Anything..." "The Grifters," "Grosse Pointe Blank," and many more.

Piven had nothing but glowing things to say about Cusack while promoting "Serendipity," telling The Orlando Sentinel that they'd known each other since they were only 8 years old. "Johnny and I are kindred spirits, maybe even soulmates. Who knows? Maybe a friend can be that for you," he mused. "[W]e love hanging out together and working together. We make each other laugh."

Unfortunately, Cusack and Piven's relationship evolved from friends to foes. After "Entourage" made Piven a star in his own right, he spoke with Best Life magazine (via The Washington Post) about the state of his friendship with Cusack. In the interview, Piven implied that Cusack felt threatened that he was no longer playing a sidekick. "I was always proud of him, and I was always in his corner. Always," Piven explained. "It just says so much about a person if he has space for other people's success."

John Cusack's family is full of megastars, including siblings Ann Cusack and Bill Cusack, but the biggest breakout star of the Chicago family is definitely Joan Cusack. The "Addams Family Reunion" actor has co-starred with her brother in at least 10 films, by each other's side in projects like "Martian Child," "High Fidelity," "War, Inc.," and "Sixteen Candles."

They also both starred in "Say Anything..." an iconic moment for John's career; who can forget him holding that boombox over his head while that Peter Gabriel song plays loudly? At a 2025 screening of the Cameron Crowe film (via People), John remembered what it was like to work with his sister on that movie. "It's easy to work with your sister," he explained. "What happens is she'll come in and then I'm in the scene with her. She runs me over like a Mack truck and they say print it, and then it's everyone's favorite thing in the movie."

While promoting "War, Inc." in 2008, Joan told The New York Daily News that her brother barely even has to ask before she's willing to sign on to one of his projects. "I'm so supportive and so admire his willingness to go out on a limb," she said. "If he can make a movie [then] I'm just ready to go." John joked that his frequent casting of his sister had another motive, teasing, "[S]ometimes the only way I can get to see Joanie is if I give her a call time."

John Cusack has been honest about the downside of fame at a young age, admitting regularly in interviews that he partied too much when he was younger. "I've been the guy on the cover of those magazines, and I've slept with some of the girls on the covers of those magazines," he mused to The New York Times in 2000 (via The Orlando Sentinel). "It's all designed to create envy because no one really exists in that form."

It makes sense, then, that Cusack once befriended someone else known for commenting on the seductive dangers of life in the fast lane: gonzo journalist Hunter S. Thompson, the writer behind "Fear and Loathing in Las Vegas." Cusack initially approached Thompson about adapting the book into a play before Johnny Depp wound up with the lead role in the film, but Cusack told Starz that he also just wanted to be Thompson's friend. The two stole cars together and drank whiskey, and it worked. "He would really get ... like he'd been shot with adrenaline," Cusack said, "when he knew somebody had some qualities of friendship and loyalty that he thought superseded everything else in the world."

He later spoke about their occasionally contentious relationship in an interview with Shortlist, recalling that the writer had a temper. "If you were friends with Hunter, you were really tight with him. But he was also someone not to be f***ed with," Cusack said. "He could be dangerous."

There are several reasons why it seems like Hollywood won't cast John Cusack anymore, and his willingness to publicly trash his movies might be one! "I've made 10 good films. I'm sure you know which ones they are," he told The Guardian in 2007. "The ones that suck I tend to blank out," he said. "It's like I never even made them."

It's safe to say there's one movie that wouldn't make Cusack's list of his good ones: "Better Off Dead," a 1985 comedy about a high schooler dealing with depression. In an interview with The Sneeze, director "Savage" Steve Holland said he and Cusack got along great while shooting the film. "I had met John when he was 17. We went to Yamashura and had drinks, which was totally illegal, and he was just the coolest guy. He was just so much fun," Holland recalled. Even after the movie was in the can, Holland said he and Cusack hung out. "He actually came to a lot of the editing. We were really good friends," he said. "We had a lot of fun."

Cusack agreed to star in Holland's next film, "One Crazy Summer." Unfortunately, he didn't see the finished "Better Off Dead" until they started shooting "One Crazy Summer," and when Holland screened his suicide comedy for the cast and crew of the next one, Cusack was upset. "John walked out of the movie. About 20 minutes into it, he walked out, and he never came back," Holland said. The actor confronted him the next day. "'Better Off Dead' was the worst thing I have ever seen," Cusack told him. "I will never trust you as a director ever again, so don't speak to me." 

Though John Cusack is known for working with the same people regularly, often finding roles for his friends and family members in his projects, he also doesn't shy away from helping launch the careers of talented newcomers. In 2000, that included Jack Black, whom Cusack got cast in "High Fidelity," skyrocketing him to superstardom.

"John Cusack was a friend from The Actors' Gang Theater Company," Black told NPR, shouting out the troupe, which also included Cusack's friend Tim Robbins. Cusack saw Black act with that group, and he also came to see Black's shows with Tenacious D, his comedic rock band. When the star of "Hot Pursuit" offered him the role in "High Fidelity," Black didn't even know if he wanted to get into film. "I was afraid. I was afraid people were going to judge me," Black said, confessing that he even pretended his hesitation was due to the way the Cusack-penned script discussed musicians he admired, like Kurt Cobain.

He went for it, and the helping hand from Cusack opened doors for Black everywhere. He quickly went on to be part of the cast of "The Holiday," "School of Rock," "King Kong," and many more, and it was all thanks to Cusack offering his friend a leg up.

It makes sense that most of John Cusack's friends and collaborators have been other people in the entertainment industry. He's been close with many other actors, a few directors, and writers of several different kinds. And then there's his friendship with Michael Jordan, legendary basketball player for the Chicago Bulls. In a 2020 appearance on "Jimmy Kimmel Live" (via Facebook Watch), Cusack revealed that he and Jordan used to go barhopping together at the height of their respective fame. "There were no cellphones," Cusack said. "There were no pictures, so you could kind of get lost in a bar pretty well."

Kimmel pointed out that Cusack and Jordan are both Chicago icons, and the "Chi-Raq" star refused to accept the compliment. Compared to Jordan, he said, he's just a fan. "I geek out!" Cusack said about their hangouts, revealing that he likes to ask Jordan questions about sports, about his opinions of other athletes. When Kimmel displayed a photo of Cusack sitting courtside watching as Jordan faced the late Kobe Bryant, Cusack shared a fun fact with the host. "I remember every game Michael played," he said, specifying that the whole audience was waiting for that moment between Jordan and Bryant. They collided, and Jordan fell, and Cusack said the "Be Like Mike" star looked up and said, "Everybody in the f***ing building knew you weren't gonna pass."

As Kimmel's audience laughed, Cusack got poetic about watching his friend be knocked down by a younger player. "You really felt the passing of the torch," he said. "One great to the other."