How One Big Risk Got John Cusack 3 Hit Movies in a Row

John Cusack is a prolific actor, despite his recent run of B-grade titles that have slowly begun to chip away at what was once a legendary film career. Truth is, he can probably do whatever he likes until he gives it all up and still walk away with a long list of classic films that cement his legacy. Beginning in the 1980s, he emerged as a fresh talent with a unique look and style that cleanly separated him from the usual stock, able to be the wholesome boy next door type while still sort of Hollywood hunky. With comedies like Better Off Dead and The Sure Thing (above) giving him center stage to shine, he slowly and steadily built an impressive catalog of performances, making him a popular face for much of the 80s and 90s. Career defining turns in the 1989 drama Say Anything … and 1990s The Grifters marked him as box office gold, which he cashed in well for years. Then came an artistic breakthrough, one that would reshape the man for the new millennium and reset our expectations with a trio of departures that proved high stakes choices. And it began with a very small door …

Being John Malkovich

By 1997, Cusack appeared to be running out of steam. Minor hits like Grosse Pointe Blank were growing less frequent, with Con Air more a win for Nicholas Cage than him. He was mostly cast in supporting roles and a few flops, leaving him an actor who seemed fated to his past. Then came Charlie Kaufman, a wickedly crafty writer who would be behind a string of offbeat, wildly inventive films that tested audiences in ways few movies had to that point. Cusack, looking to go big, told his agent to get him something crazy, and so he did, putting the outrageous Being John Malkovich (1999) in his lap. While the film is without a doubt a monumental acting achievement for Malkovich, who stars as himself, Cusack (who worked earlier with Malkovich in Con Air) really stretches his wings here playing a failed puppeteer forced to work as a file clerk on the 7th (and a half ) floor of an office building (that’s a gag that works all on its own). He then finds a tiny door behind a filing cabinet that, when he finally crawls through it, serves as a portal into the mind of none other than Mr. Malkovich. Wish you had thought of that? A lot of people did. Quirky and eccentric, this is a smart, funny, and slightly tragic story that was either going to bomb so badly no one involved would ever work again or be such a hit, it would change everything. It was the latter and suddenly Cusack was on the start of a run the likes he has yet to see again, following this as a man spinning records in search of answers to an age old question …

High Fidelity

The following year, in 2000, Cusack was ready to take his boost from the success of Being John Malkovich and deliver something truly his own and had been already working on a little project brought to him from the makers of Grosse Pointe Blank. Based on the book of the same name by Nick Hornby (who would later pen About A Boy), Cusack and his own writing team worked on the fourth wall breaking screenplay for High Fidelity, crafting a personal project into a clever and genuinely earnest story of a young man in the throes of lost love, wondering why he can’t keep a good girl in his life. Naturally, what he discovers is that maybe it’s his own fault and goes on a mission to find out if that’s true. Unusual to say the least. Set around a backstreet record shop, the film launched the career of Jack Black (who had been working in movies for a decade) and proved Cusack was far from done as a leading man, creating another vulnerable, slightly troublesome and greatly lovable character akin to his early work in the 80s. High Fidelity is a mature, insightful film that lets Cusack really find his footing, breathing an intensity into the part that for many helped form an immediate connection with the spiralling man at the center. It’s arguably his best work and remains a classic. He would take one of the co-stars from this movie and go for three in a row …

America’s Sweethearts

I know what you’re thinking. You’re thinking, “John Cusack was in America’s Sweetheart? Wasn’t that a Julia Roberts movie?” Yes to both. And shame on you. Just kidding. It’s easy to forget the work Cusack does here, the movie more a romcom for Roberts than anything about what he does, but still, he does good in a he part, offering up just the right amount of sting. Catherine Zeta-Jones plays Gwen Harrison, a beautiful young movie star married to fellow actor Eddie Thomas (Cusack), the team often starring together in popular romantic comedies. Their latest film is about to be released, though publicist Lee Phillips (Billy Crystal) has a few problems: A) the director won’t give him a copy of the movie to view and B) Gwen and Eddie are in the middle of a nasty breakup. What’s he to do? Written by Crystal, America’s Sweethearts was a huge box office hit, tripling its budget and leaving lovestruck audiences more than satisfied, even though critics ravaged it. Nonetheless, Cusack manages to give some spark to his relatively thankless role, playing second fiddle to both Crystal and of course, Roberts, who plays Gwen’s sister and personal assistant. Either way, this is a surprisingly satisfying flick, despite its obviousness, though spells a sort of beginning of the end for Cusack, lacking the narrative mental powers of his previous two that frames the eventual lack of significant work that followed.

THE AFTERMATH

Maybe that’s a little unfair to say as Cusack did bring his A game to a few less than acclaimed movies, including 2007’s underrated Martian Child and the clever horror film 1408 among a few more efforts. However, it wasn’t until 2015’s Chi-Raq (above) when he turned heads again with a powerful take as a religious man in the heart of violence-torn Chicago. Most modern audience probably know him from the dreadful disaster movie 2012, which is too bad because he’s done a lot better than that in the last ten years. Fans of Cusack still have plenty to celebrate and even though his latest movies have been real stinkers, there’s always hope he’ll find another chance to get back on top. Until then, flip back to the old days and soak in the goodness that made his movies so fun to watch. What are your favorite John Cusack movies?