John Cusack's Most Controversial Moments

To Generation X, John Cusack will forever be remembered as the sweet, hapless Lloyd Dobler from Say Anything, standing outside with that boombox, blasting Peter Gabriel, winning over the girl. But his reputation changed, however, and as of this writing, he's  anything but sweet. In fact, as of this writing, he seems to hew much closer to his complicated character from High Fidelity, Rob Gordon — a passionate, but flawed artist, who can't seem to stop himself from speaking his mind, even at the detriment to his personal and professional life. 

With Twitter and some seriously scathing print interviews as his preferred battleground, Cusack has become quite prickly as the years have gone by, and has stirred up quite a bit of debate. Ready to see where it all went askew for this darling of 80s and 90s cinema? Here are John Cusack's most controversial moments ever.

When have memes ever gotten anyone in trouble? Oh, right. In 2019, John Cusack shared a meme on Twitter, than quickly deleted it after catching heat — because when does that go wrong? The tweet, which was screengrabbed and widely re-shared, included an image of a Star of David with text: "To learn who rules over you, simply find out who you are not allowed to criticize." To the image, Cusack added his own commentary: "Follow the money RT."

Critics took the meme to insinuate that Jewish people rule the world tyrannically via money, which is a notion that has a long, hateful history. As the Independent explained, "While the image claims the quote was from French satirist Voltaire, it was actually spoken by white nationalist Kevin Alfred Strom." Yikes. Cusack tried to talk his way out of it in other since-deleted tweets republished by the Daily Beast, and — surprise! — that backfired, too. 

"A bot got me—I thought I was endorsing a pro Palestinian justice retweet—of an earlier post—it came I think from a different source—Shouldn't Have retweeted," he wrote. That might have been the end of it, but Cusack couldn't stop. "You think Israel isn't commuting atrocities against Palestinians? What planet are you on?" he continued. Oh boy. He got slammed by everyone from journalists like Yashar Ali and Yair Rosenberg to even Ted Cruz.

John Cusack proudly wears his political affiliations on his sleeve. He's gone so far as to become a board member of the Freedom of the Press Foundation, a nonprofit founded in 2012 in response to the WikiLeaks blockade (wherein people could not donate to WikiLeaks via MasterCard, Visa, or PayPal). Taking on the U.S. government (and big banks) in this way might scare some off, but not Cusack. He remained with the organization in 2014 when controversial figure Edward Snowden joined the board, and again stayed in 2016 when Snowden became the group's president. Snowden was the whistleblower who famously fled the U.S. after exposing NSA secrets — a move that the government considered a massive breach of national security. As of this writing, Snowden resides in exile in Russia. 

A lot of actors shy away from potentially controversial (or possibly even career-killing) associations like these, but Cusack clearly doesn't. His made his thoughts on Snowden crystal clear when he published his essay, "The Snowden Principle." In it, he wrote of Snowden's actions, "From the State's point of view, he's committed a crime. From his point of view, and the view of many others, he has sacrificed for the greater good because he knows people have the right to know what the government is doing in their name. And legal, or not, he saw what the government was doing as a crime against the people and our rights." 

Before he ever joined Twitter or joined forces with Edward Snowden, John Cusack was saddled with the notorious Hollywood label of "difficult." Paul Leyden, the writer of Cusack's 2012 film The Factory, leveled the accusation against Cusack by detailing the actor's alleged bad behavior on set. 

In a zinger-filled interview with The Daily Telegraph, Leyden, not unlike Cusack himself, didn't pull any punches. His opening salvo?  "John Cusack was one of my favourite actors until I met him." Ouch. He then accused Cusack of unprofessional behavior, saying he would often arrive on-set, "hours late," adding, "He cost us a lot of money and he was getting his biggest pay day on this film. ... [He] wouldn't apologise for keeping everyone waiting in the snow . . . a real prima donna." Leyden summed up his experience working with Cusack this way: "Everyone thought he was a really nice guy (prior to filming) and all I can say is that it was a really nice day when he wrapped."

Cusack, for his part, never commented on Leyden's accusations. The film itself was unquestionably a flop, going straight to video and only grossing around $30,000 against a reported budget of $25 million. One does have to wonder if the film's critical failure drove some of Leyden's animosity toward its star. As of this writing, we may never know for sure. But we're guessing those two won't work together again!

John Cusack is a life-long bachelor. And his alleged dating history is a who's who of Hollywood actresses (although on a Howard Stern appearance in 2012, he denied dating many of them women he'd been rumored to, and would neither confirm nor deny many others). 

When asked by the press why he hasn't gotten married, in his usual style, Cusack has been pretty blunt. He gave an interview to Elle in 2009 and had lots to say about dating and relationships, including one statement that many of his exes may have taken as major shade: "Actors go out with actresses as a form of self-flagellation." Yikes. In the same interview, when asked why he's never married, he said, "Society doesn't tell me what to do."

A few years later, in the aforementioned Stern appearance, he seemed to have softened a bit, saying, "I'm sort of against divorce. I don't want to get divorced." The closest he likely ever came to marriage was with actress Neve Campbell, with whom he was on-again, off-again (and allegedly stormily so) for years. But as of this writing, Cusack is still unmarried.