Best known as the star of Say Anything…, High Fidelity and Being John Malkovich, John Cusack’s career ranges from warm teen romances to black comedies. But throughout his work, Cusack made his name in playing offbeat, unpredictable characters. Here are some surprising facts about the outspoken and talented Hollywood star.

20. He filed for legal emancipation from his parents for a film role

Cast in The Sure Thing aged only 16, Cusack was not legally permitted to remain on set without a parent.


During casting, director Rob Reiner was reluctant to even meet with Cusack, believing that he was too young for the role.

Jane Jenkins and Janet Hirshenson, the casting directors, persuaded Reiner to give Cusack the audition, where Cusack swiftly secured the iconic role.


As he was underage throughout the film’s creation in California, and his family was based in Illinois, Cusack had to formally leave his parents’ guardianship.

His family sought paperwork for producer Roger Birnbaum to become his legal guardian during filming.


Released in 1985, this modest rom-com grossed over $18 million at the box office.

19. He almost took the male lead role in 2002’s Chicago

Cusack was considered to play Billy Flynn, the slick, tap-dancing lawyer embroiled in Chicago’s death row cases.


The role included a puppeteering scene, which would have followed on fittingly from Cusack’s marionette work in Being John Malkovich.

However, he lost the part to Richard Gere, who received critical acclaim for his singing and dancing in the movie.


Cusack instead starred in the rom-com Serendipity in 2002.

In the same year, he also took on the far more chilling role of Max Rothman in Max, a drama about a fictional Jewish art dealer who befriends a young Adolf Hitler.


Cusack has said that the scripts of Max and Being John Malkovich were the best he ever read.

18. He’s a fan of helicopter snowboarding

In his spare time, Cusack takes to the slopes for helicopter snowboarding.


This adventurous sport involves flying out to mountains that are too remote to reach by cable car.

Cusack’s on-screen roles have sometimes overlapped with snowy vistas. In the comedy Hot Tub Time Machine, Cusack plays one of three friends who discover a time machine at a ski resort. Filming took place at the Fernie Alpine Resort in Canada.


Cusack’s character Lane also takes a tumble while skiing in Better Off Dead.

Cusack also enjoys travelling by helicopter to see remote glaciers in Alaska.


He owns two motorbikes, which he has used for road trips around South America.

17. He once dated Britney Spears and Pamela Anderson

Among Cusack’s rumoured former girlfriends are Pamela Anderson, Jodi Lyn O’Keefe and Uma Thurman.


He has also been coupled with Alison Eastwood, Jennifer Love Hewitt and Britney Spears.

After co-starring as romantic leads Martin and Debi in Grosse Pointe Blank, Cusack and Minnie Driver also started a relationship.


In spite of his pursuit of women – or perhaps because of them – Cusack has never married or announced an engagement.

Meg Ryan, star of When Harry Met Sally…, is also among Cusack’s former girlfriends.


Cusack played the love interest to Ryan’s Anastasia in the 1997 film of the same name, an animated classic about the fate of the Russian royal family.

16. He has a level six black belt in kickboxing

Cusack’s passion for kickboxing flourished while he was preparing to play Lloyd Dobler in Say Anything… in 1989.


He kept up the sport long past the end of filming and trained with former world champion Benny Urquidez for two decades.

Cusack and Urquidez also collaborated for Con Air, Grosse Pointe Blank, The Contract, 1408 and Dragon Blade.


Cusack has an impressive level six black belt in the Ukidokan kickboxing system, which Urquidez founded.

This training came in handy as he practised stunts for Dragon Blade amid a multilingual cast.


“I’ve been doing martial arts for so long, I understood the body rhythms even if I didn’t understand the commands,” Cusack told the Straits Times.

15. He very nearly played John Bender in The Breakfast Club

Cusack was chosen to play John Bender in The Breakfast Club, the final principal role to be cast.


Just before shooting began, however, director John Hughes had a sudden change of heart.

Hughes felt that Cusack was not quite menacing enough to pull off John Bender’s brooding persona.


Instead, he picked Judd Nelson from the auditions’ runners-up. Nicolas Cage was also considered for the part.

Despite missing out on this particular role, Cusack remained close to the so-called Brat Pack.


His prominent teen movies include the classic Sixteen Candles, in which he starred alongside Anthony Michael Hall and Molly Ringwald.

14. Producers didn’t want Cusack for Better Off Dead because they thought he was “a bit of a nerd”

Director Savage Steve Holland fought hard to convince producers that Cusack could handle the starring role in Better Off Dead.


Holland later said that Cusack’s character was “a bit of a nerd” in Sixteen Candles, which was off-putting to the studio.

Nevertheless, Holland won, and Cusack was cast as the lead in this surreal black comedy.


It wasn’t particularly successful at the box office, but Better Off Dead and its dark humour eventually achieved cult classic status.

The young star apparently detested Better Off Dead upon release – director Savage Steven Holland said that Cusack stormed out of the first screening after 20 minutes.


But from this oddball part, Cusack has gone on to star in impressively wide-ranging and frequently dark roles, from the Victorian poet Edgar Allan Poe in The Raven, to co-founder of the Beach Boys, Brian Wilson, in Love and Mercy.

13. He puts his favourite bands into his movies

In many of his blockbusters, Cusack manages to sneak in references to the bands that he loves – most notably The Clash and The Ramones.


Usually his character will wear a band-branded T shirt, for example in Say Anything.. and High Fidelity.

But in Grosse Pointe Blank, Cusack included a whole poster for The Future Is Unwritten, a documentary about The Clash singer and guitarist Joe Strummer.


In fact, Joe Strummer wrote the score for Grosse Pointe Blank, giving Cusack the opportunity to work with one of his favourite celebrities.

The Clash heavily influenced Cusack’s lead role in Say Anything…, as he told The Current in an interview.


“I thought that the character [Lloyd Dobler] didn’t have enough dimension at the time, more of a worldview, politics, you know?” he said. “I was listening to The Clash, so I wanted him to have thoughts outside of his high school, or county, or state; to think about the world the way people do when they’re young.”

12. He took Being John Malkovich because he wanted something “unproduceable” and “bizarre”

With his penchant for unusual roles, Cusack sought out only the most interesting parts once he reached stardom.


In an interview with The AV Club, he recalled telling his agent William Morris, “Give me the craziest, most unproduceable script you can find… give me something that is just the most bizarre thing you’ve ever read.”

Morris presented him with the script to Being John Malkovich, and Cusack was instantly hooked.


To prepare for the role, Cusack had to take lessons in marionette puppetry.

Cusack’s character, an out-of-work puppeteer in NYC, is named Craig Schwartz.


This name refers to both Bruce Schwartz, a famous puppeteer, and Edward Gordon Craig, an actor who famously compared actors to marionettes.

11. He turned down lead roles in Apollo 13 and Indecent Proposal

Cusack rejected the role of astronaut Fred Haise in the Oscar-winning Apollo 13, which was snapped up by Bill Paxton instead.


Meanwhile, Cusack starred in City Hall with Al Pacino.

The pair starred as a mayor and deputy mayor in the 1996 crime drama.


On working with Al Pacino, he told NJ Entertainment, “I was scared to death at first, but he was so generous with me, as a person, as another actor, it was just tremendous.”

He also gave up the role of David Murphy in the drama Indecent Proposal – a part that was also rejected by Charlie Sheen.


Instead, Woody Harrelson took the part; the film grossed nearly $267 million worldwide.

10. Jeremy Piven was his childhood friend

Jeremy Piven’s parents ran a theatre workshop in Illinois, which the young Cusack attended.


While Piven’s parents were working on a production of The Seagull, Cusack and Piven took it in turns to play the role of the child.

Working together from the age of eight, the pair became firm friends, and eventually lived together in an apartment in Chicago.


The duo later became co-stars, appearing in ten films together including Serendipity and The Grifters.

In their collaborative films, Piven typically portrayed Cusack’s wise-cracking sidekick.


But Piven soon achieved stardom away from Cusack in Entourage, Mr Selfridge and Ellen.

9. He was originally meant to star in Watchmen, but was dropped by Zack Snyder

Director David Hayter planned for years to bring Watchmen to the big screen.


Cusack, as a massive fan of the superhero team, was Hayter’s top choice for Nite Owl II, a tech whizz with superhuman strength.

Jude Law, another fan of Watchmen, was also eager to take part in the film, vying for the role of Ozymandias.


When Hayter’s production fell through, however, Zack Snyder took over as director. Cusack continued to pursue the role.

“I haven’t read the script nor have I ever met Mr Snyder,” said Cusack in a 2007 interview with MTV. “I thought that was a really, really cool comic. I’m into it.”


But Patrick Wilson was Snyder’s first choice for the 2009 film, and so Cusack missed out on the chance to play a superhero. Matthew Goode ultimately took the role of Ozymandias, leaving Jude Law disappointed also.

8. He’s been involved in the anti-war movement since childhood

When Cusack was a child, his parents were close friends with the religious anti-nuclear activists and brothers Peter and Daniel Berrigan.


An Irish Catholic family, the Cusacks cared deeply about the anti-war movement of the 1970s.

Image: Clara Sherley-Appel

Cusack’s mother was arrested multiple times for joining political protests.


According to author Gary Wills, the entire Cusack family was questioned by the FBI while Daniel Berrigan, or Father Dan, was fleeing arrest.

Cusack’s interest in activism continues to this day. He wrote political blogs for the Huffington Post, and was vocal in his opposition to the war in Iraq.


He has often expressed his anti-war stance, saying on social media: “Being anti-war is pro-troops – pro-human.”

7. He’s an avid fan of the Chicago Cubs

This Hollywood star is a serious fan of baseball, with one team in particular standing out to the Illinois native.


He and his siblings have long supported the Chicago Cubs.

Last year, Cusack was caught up in controversy when a fan photographed him apparently refusing to stand up for the mid-game military parade.


He fiercely defended himself on Twitter, saying that he simply “didn’t stand up fast enough” for his accusers.

Cusack tries to attend every game at Wrigley Field that he can.


“It’s hard for people who have normal sports relationships to teams to understand,” he told MLB. “Rooting for a team that’s never won [the World Series] in your lifetime, in your father’s lifetime, it’s just different. The vibe around Wrigley is just different.”

6. He only ever made ten good films, in his opinion

Despite appearing in a staggering 79 films, Cusack doesn’t think many of them were particularly good.


In 2007 he said he had “only ever made ten good films” and claimed, “The ones that suck I tend to blank out. It’s like I never even made them.”

“Well, there aren’t forty that are great, put it that way. But that’s fine. Ten is a good batting average.”


On his film choices, Cusack says he likes to be adventurous. “I like to take risks,” he said in an interview with the Guardian. “With acting, you wanna see if you can get into trouble without knowing how you’re gonna get out of it.”

Outside of his own work, one of Cusack’s all-time favourite films is the war epic Apocalypse Now.


“I remember coming out of that and I almost couldn’t speak,” he reminisced in an interview with Rotten Tomatoes. “Stunned.”

5. He once met whistleblower Edward Snowden in a Moscow hotel room

Renowned for his activism, Cusack has never shied away from debates around press freedom and civil liberty.


He arranged for himself, the Indian author Arundhati Roy, and military analyst Daniel Ellsberg to meet with the whistleblower Edward Snowden in 2015.

Snowden was hiding from US officials in a hotel in Moscow after leaking National Security Agency (NSA) material.


In this secretive meeting, the group talked about the CIA, surveillance and the nature of fame.

Cusack and Roy later co-authored a book about this meeting, entitled Things That Can And Cannot Be Said.


Roy wrote in the Guardian after the encounter: “John Cusack, who thought up and organised this whole disruptive enterprise, comes from a fine tradition, too – of musicians, writers, actors, athletes who have refused to buy the bulls***, however beautifully it was packaged.”

4. All four of his siblings are actors

Cusack’s father, Richard Cusack, was an actor and filmmaker – and his five children followed suit.


In fact, four of the siblings – John, Joan, Bill and Ann – appear in Grosse Pointe Blank, a 1997 black comedy that John helped to write.

Raised in Illinois, John attended the Piven Theater Workshop together with two of his sisters.


Other famous alumni of the workshop include Aidan Quinn, Lili Taylor and Julian Bailey.

John’s second eldest sister is Joan Cusack, the award-winning comedian and screenwriter.


Working with siblings isn’t always easy. On working with Joan for Grosse Pointe Blank, John Cusack told CBR: “I basically write some stuff on the page and get on set, and then she says whatever the f*** she wants.”

3. Fall Out Boy’s song Honorable Mention is about him

“I said I hate you but I’d never change a thing / I can be your John Cusack,” sang US rock band Fall Out Boy in 2003.


The band’s song, Honorable Mention, features on their mini-LP Fall Out Boy’s Evening Out With Your Girlfriend.

While writing their ode, Fall Out Boy may well have looked to High Fidelity, the 2000 comedy where Cusack stars as a lonely record store worker.


Soundtrack choices for High Fidelity were fiercely contended, with screenwriters considering over 2000 songs.

A keen fan of punk music, Cusack appeared as a guest DJ on KCRW Radio Station in 2008.


Among his picks were Billy Bragg, Elvis Presley and Strauss and Ray Davies.

2. His character in the film 2012 was named after 50 Cent

In the blockbuster disaster film 2012, Cusack starred as Jackson Curtis, a struggling writer and desperate father.


Writer and director Roland Emmerich is a big fan of 50 Cent, and so he took the rapper’s birth name – Curtis Jackson – and flipped it to name the movie’s hero.

Filmed variously in China, Japan, Vatican City, the States and Canada, this film had a production budget of $200 million.


It was among the highest-grossing films of 2009, despite its mixed critical response.

The film was inspired by Western myths around the Mayan calendar, suggesting that the world would end in 2012. In fact, the Mayan calendar featured no such deadline.


Emmerich told USA Today that this would be his last ever disaster movie, but he went on to make several more – including Independence Day: Resurgence in 2016.

1. He actually played Fishbone’s Turn the Other Way for the iconic boombox scene in Say Anything…

While filming the famous boombox scene in the 1989 classic, Cusack was actually playing one of his favourite Fishbone hits.


Cusack was initially reluctant to do this scene, as he felt it didn’t fit his character.

He agreed with producers that he would play his chosen song during filming, helping to add defiance and attitude to his performance.


The song In Your Eyes was added to the scene afterwards, completing the unforgettable moment.

The scene has seen countless parodies and homages in other media, from Deadpool 2 to Orange Is The New Black. Skankin’ To The Beat by Fishbone, Cult Of Personality by Living Colour, and Joe Satriani’s One Big Rush also feature in the film.