I Gave Her My Heart, She Gave Me a Pen: John Cusack’s 10 Greatest Roles

John Cusack has, over his 30 plus year career, defined the lovable Rom-Com Good Guy. His soft features and just slightly geeky idiosyncrasies have made him the big screen spokesman for the “cool nerds” who find themselves pining after the girl and fighting their way out of the friend zone. But let’s not pigeonhole John Cusack, who has stepped away from his lovable pre-hipster persona over the years to tackle genre films, straight dark comedies, dramas, and one seriously captivating Charlie Kaufman film.

Whether he’s blasting Peter Gabriel, searching for the killer, skiing for the girl, or being dumped in a ditch on the New Jersey Turnpike, John Cusack has remained forever watchable, endlessly charming even in his more sinister turns. Here are his 15 greatest performances:

John Cusack - the Ice Harvest


10. The Ice Harvest – One of a handful of John Cusack’s incredibly overlooked roles is this Harold Ramis whiz bang caper comedy. Cusack plays Charlie Arglist, a scummy lawyer who, with the help of his even scummier partner Vic (Billy Bob Thornton), have embezzled $2 million and are looking to skip town. Charlie wants his strip club owner girlfriend to take off with him, but an ice storm derails these best laid plans. The Ice Harvest is a somewhat standard, but charming, comedy of errors evolving into a high-energy escape film with a dozen plates in the air. And Cusack shows off one of his greatest strengths as an actor: his bottled-up frustration with the chaos surrounding him.

John Cusack - Identity

9. Identity – Cusack left all his Rom-com charm behind for Identity, a straightforward genre thriller with a narrative structure that is anything but straightforward. Don’t bother digging into the logic of the film, just enjoy the ride. Cusack is one member of an all-star cast of undercard stars, from Ray Liotta, to Amanda Peet, to Jake Busey, John Hawkes, John C. McGinley, Rebecca De Mornay, and Alfred Molina. A collection of travelers are stranded at a seedy motel in the middle of a serious storm, and before long they are picked off one-by-one. Something sinister is at play here, and again Cusack is playing the steady center of whirling madness.

John Cusack - Con Air

8. Con Air – How can you leave a movie off John Cusack’s list where the guy had the balls to roll into a Jerry Bruckheimer film wearing sandals with socks? Sure, Con Air is Nicolas Cage’s movie, and John Malkovich’s movie, and on and on as we check off the impressive list of convicts aboard this doomed aircraft. But Cusack’s Vince Larkin is the Cusack persona from those 80s teen movies all grown up and given an honest gig. And without his snarky insight on the ground, nobody would have gotten anything done to help Cameron Poe land these prisoners. And he’s wearing sandals with socks!

John Cusack - Say Anything...

7. Say Anything… – Cameron Crowe’s directorial debut is half a great film, half an okay film that gets lost in the weeds of a less interesting subplot. Cusack is Lloyd Dobler, and this is the role that cemented his status as the lovable “Other Guy.” Dobler is not the Most Popular, he isn’t The Most Likely to Succeed, he’s simply the guy everyone thinks is “kinda cool.” He has his beliefs, he marches to the beat of his own drum, and his uniqueness eventually makes its mark on Diane. His romance with Ione Skye’s Diane is honest, true, but eventually overloaded with saccharine charm in the film’s most iconic Peter-Gabriel’d boombox moment. If only Crowe hadn’t become so preoccupied with Diane’s father and his legal troubles…

John Cusack - the Grifters

6. The Grifters – Another criminally overlooked Cusack gem has him playing two sides of a con game, one involving his estranged mother (Angelica Huston), and the other his girlfriend, Myra (Annette Bening). Once again it is Cusack in the middle of a whirlwind, able to charm his way in and out of situations. Stephen Frears’ film is put together as efficiently as a Swiss Watch, and Cusack’s rapid-fire dialogue delivery is on full display. And, somehow, Cusack was left out of the Oscar nominations that year when both his female costars nabbed nominations.

John Cusack - Love & Mercy

5. Love & Mercy – Here was another time when John Cusack flirted on the edges of an Oscar nomination. Love & Mercy, the story of troubled Beach Boys frontman Brian Wilson, was arguably more Paul Dano’s film than Cusack’s, and Dano was given the meatier portion of Wilson’s extended nervous breakdown. Cusack plays the singer in the 80s, already broken and under constant supervision of an unsavory Doctor. It is a heartbreaking dual turn from Dano and Cusack, and Cusack’s version of Wilson shows him falling in love in his darkest days.

John Cusack - Better Off Dead

4. Better Off Dead – Here is where John Cusack became John Cusack. He is Lane Myer, who is dumped early on because his girlfriend thinks it would be in her best interest to date someone more popular, maybe better looking. Maybe someone who drives a better car. Somebody like the captain of the ski team. It’s the defining plight of the “Cusackian” character, being tossed aside for the jock. This drives Lane into thinking up creative ways to off himself. Better Off Dead spins out of control in gleefully 80s ways, from a mom with terrible cooking, to a wacky neighbor, to an annoying paperboy, to an eventual ski race where Lane sees a chance to win his woman back.

John Cusack - high Fidelity

3. High Fidelity – The Cusack Brand is given an introspective makeover in High Fidelity, as Cusack’s Rob Gordon, a record store owner, speaks directly to the audience about his past loves and the nutcase who run his record store. Rob Gordon was a hipster before hipsters were a thing, pining over lost loves and holding them up agains the music that was prevalent in his life at the time. This is one of the most balanced films in Cusack’s career, funny and poignant and full of energy.

John Cusack - being John Malkovich

2. Being John Malkovich – Craig Schwartz is an out of work puppeteer with a homely wife (Cameron Diaz) – who has a pet monkey. Sure, that might be odd, but consider the rest of the story: Craig gets a job with a man who’s apparently well over 100-years old at an office that’s a half floor in a building. A half floor. At this job he pines over a sexy coworker (Catherine Keener) and finds a portal that takes you into the mind and POV of John Malkovich. Charlie Kaufman’s screenplay, directed by Spike Jonze, is one of the most unusually inventive movies ever made, and Cusack plays Craig as a scumbag we still can’t help but root for in the end.

Johnn Cusack - Grosse Point Blank

1. Grosse Point Blank – George Armitage’s comedy thriller hybrid stars Cusack as an assassin who must travel to his hometown to wipe out a target. It just so happens that it’s his 10-year reunion. Cusack is pitch perfect as Martin Blank, and this is his best teaming with Jeremy Piven back when Piven was an ace sidekick before he turned into Ari Gold. And Minnie Driver as the love interest is another spot on casting choice. Grosse Point Blank subverts the 80s high school comedies that made Cusack so popular by having him infiltrate this homogenized universe as a cold-blooded killer. And Cusack plays a killer like you would expect: “Hi. I’m, uh, I’m a pet psychiatrist. I sell couch insurance. Mm-hmm, and I – and I test-market positive thinking. I lead a weekend men’s group, we specialize in ritual killings. Yeah, you look great! God, yeah! Hi, how are you? Hi, how are you? Hi, I’m Martin Blank, you remember me? I’m not married, I don’t have any kids, but I’d blow your head off if someone paid me enough.”



Larry Taylor - Managing Editor
Larry Taylor - Managing Editor
Larry is the managing editor for Monkeys Fighting Robots. The Dalai Lama once told him when he dies he will receive total consciousness. So he's got that going for him... Which is nice.