20. The Journey of Natty Gann (1985)
It’s the Great Depression, Disney-style, as a tomboy named Natty hops trains to find her lumberjack father. This was the first time I saw Cusack, who’s impressive as a wise young hobo—though not the first time I saw Natty’s wolf-dog companion. That’s Jed, the sled dog from The Thing!
19. Tapeheads (1988)
Mike Nesmith of the Monkees produced this silly, very 1980s slapstick comedy, which has a cult supporting cast and a great soundtrack. Cusack (with a sleazy mustache) and Tim Robbins play losers whose rock video company takes off after a Skylab-related tragedy.
18. High Fidelity (2000)
Cusack briefly goes back to his teen movie persona, but he’s too cool to be convincing as the list-making manchild from Nick Hornby’s novel, now set in Chicago. If you don’t mind women being shown as killjoys with bad taste in music, this look at commitment-phobic masculinity and pop culture gatekeeping is light, shallow fun.
17. Max (2002)
In 1918 Munich, Cusack plays a Jewish gallery owner who encourages the artistic dreams of a bitter army veteran (Noah Taylor) who has a talent for anti-Semitic speeches. This Hitler origin story could have used more Ken Russell-style flair, despite some striking performance art where one-armed Cusack sinks naked into a giant meat grinder.
16. Say Anything… (1989)
Just before moving on to adult roles, Cusack made one last teen rom-com in Cameron Crowe’s directorial debut. Lloyd Dobler is a slacker who falls for the smartest girl in school. Their on-and-off romance includes that iconic boombox courtship scene, plus great supporting turns from Lili Taylor and Cusack’s sister Joan.
15. Con Air (1997)
Amid over-the-top performances from John Malkovich and Ving Rhames as convicts who hijack their plane, Cusack plays the understandably sweaty U.S. marshal watching from the sidelines. Nicolas Cage is the heroic prisoner on parole who has to stop the psychos in this silly but entertaining action movie.
14. Fat Man and Little Boy (1989)
Paul Newman stars as General Groves (played by Matt Damon in Oppenheimer), who’s in charge of building the first atomic bomb. But it’s Cusack who sticks in your memory as a (fictional) scientist who suffers the consequences of a lab accident. “Everybody should make it,” he says after doing some math, “except me. I’m going to die.”
13. Bullets Over Broadway (1994)
As the Woody Allen stand-in in one of Allen’s funnier post-Farrow comedies, set in 1920s New York, Cusack plays a playwright who gets his show funded by casting a gangster’s girlfriend—only to find her mobster bodyguard is a better writer than he is. Oscar-winning Dianne Wiest is hilarious as an alcoholic actress. “Don’t speak!”
12. The Sure Thing (1985)
Before his small role in Rob Reiner’s Stand By Me, Cusack starred in the same director’s excellent teen twist on It Happened One Night. “Gib” Gibson is a beer-guzzling slob whose plan to sleep with a California beauty gets derailed when he shares a cross-country trip with a prim fellow student.
11. Eight Men Out (1988)
John Sayles’ careful period drama is a great introduction to the Chicago Black Sox scandal, a key reference in American pop culture. A group of baseball players, angry that management won’t give them a deserved bonus, agree to throw the 1919 World Series. In a strong ensemble cast, Cusack takes on one of his first adult roles as the unlucky shortstop, Buck Weaver.
10. 2012 (2009)
Can sci-fi novelist Cusack reunite with his wife before director Roland Emmerich destroys the planet with solarSolar flares, tsunamis, and volcanic eruptions? Naturally, the billionaires have come up with a plan to survive this disaster movie with a death toll in the billions. It’s just too bad they don’t all end up like Cusack’s love rival, who gets killed off in the most twisted way possible.
9. The Paperboy (2012)
This crazy slice of Southern gothic is best known for Nicole Kidman peeing on Zac Efron’s jellyfish stings. But Cusack really lets loose as a swamp-dwelling, alligator-hunting racist creep with a sad Nic Cage haircut. You haven’t truly lived until you’ve seen Kidman bring him to orgasm in the prison visiting room!
8. Grand Piano (2013)
A nervous pianist (Elijah Wood) gets a message during a concert: “Play one wrong note and you die.” Cusack oozes smarmy menace in a mostly voice role as the villain in this ridiculous thriller. Eugenio Mira can’t seem to direct a single scene of Damien Chazelle’s script without doing something adorably crazy with it.
7. Identity (2003)
Ten people stranded by a rainstorm at a remote Nevada motel get murdered one by one in James Mangold’s psycho-thriller, which feels like And Then There Were None. Cusack plays an ex-cop who reads Sartre and tries to solve the mystery. He stumbles onto a plot twist that annoyed me the first time I saw it, but turned out to be a lot more fun on a rewatch.
6. Maps to the Stars (2014)
Deep into his villain phase, Cusack is chilling as a celebrity therapist. His karma comes in the form of his pyromaniac daughter, who arrives in Los Angeles to confront her family and its dark secrets. David Cronenberg pulls no punches in this grim but great Hollywood satire. Julianne Moore gives a fearless performance as a drug-addled movie star with constipation.
5. Love & Mercy (2014)
This non-linear Brian Wilson biopic weaves together Paul Dano as 1960s Wilson and Cusack as the heavily medicated 1980s version. In the ’60s, he’s revolutionizing pop music with inspired tinkering in the studio, but already struggling with mental illness. In the ’80s, he’s under the control of an evil doctor, but redeemed by the love of a good woman.
4. 1408 (2007)
A writer checks into a haunted hotel room, where he has to deal with not just ghosts but his own traumatic past in this spooky adaptation of a Stephen King story. Despite a brilliant cameo from Samuel L. Jackson, it’s basically a one-man show for Cusack. He rises to the occasion with a virtuoso performance, moving from skepticism to paranoia and yelling at the fridge.
3. Grosse Pointe Blank (1997)
Two years before Tony Soprano had his first anxiety attack, Cusack co-produced and co-wrote this black comedy about a depressed hitman (Alan Arkin is hilarious as his therapist) attending his high school reunion. The tone is mostly lighthearted, but there are dark hints about the moral relativism of modern America. Cusack perfectly embodies deadpan cool.
2. The Grifters (1990)
Cusack definitively left teen movies behind with his performance as a cute but shady conman in this cracking adaptation (by Donald E. Westlake) of Jim Thompson’s hard-boiled 1963 novel about a trio of small-time scammers. A bleached-blond Anjelica Huston plays his mom, and Annette Bening plays his sexy girlfriend. It’s lowlife Greek tragedy with fantastic performances and an unforgettably bleak ending.
1. Being John Malkovich (1999)
Cusack asked his agent for the “craziest, most unproduceable script you can find,” and the result was Spike Jonze’s feature-directing debut. Cusack, with the saddest hair imaginable, has a blast exploring his dark side as a grumpy street puppeteer who discovers a secret portal into the mind of actor John Malkovich. And that’s just the beginning of Charlie Kaufman’s wild story.Kaufman’s endlessly inventive story blends questions of identity, sexuality, and control into a surreal mix, made even more effective by a straightforward, no-frills approach that avoids flashy special effects.
Frequently Asked Questions
Here is a list of FAQs about John Cusack movies ranked from worst to best with clear direct answers
The Worst Tier
1 Why does Hot Tub Time Machine 2 feel like a bad fever dream
Answer Because its a cashgrab sequel that loses the originals heart and humor Cusack isnt even in it and the plot is a nonsensical crude mess
2 Is The Raven actually about Edgar Allan Poe solving murders
Answer Yes but its a terrible gothic detective movie Cusack plays Poe as a grumpy drunk caricature and the mystery is boring Skip it unless you love bad period pieces
3 What went wrong with 2012
Answer Its a loud ridiculous disaster movie where Cusack plays a struggling writer who somehow saves the world The CGI is overthetop the plot is laughable and its only fun if you want a so bad its good experience
The Average Tier
4 Is Grosse Pointe Blank actually good or just overhyped
Answer Its genuinely good but not his best Cusack plays a hitman attending his high school reunion Its witty dark and has great 80s music but the action feels dated Its a solid cult classic not a masterpiece
5 Why do people love High Fidelity so much
Answer Its a relatable painfully honest look at breakups and obsession with music Cusacks character Rob is a jerk but you root for him Its a mustwatch for music nerds and anyone whos been dumped
6 Is Say Anything the best teen movie ever
Answer Its a toptier teen classic but not the best ever The famous boombox scene is iconic but the movie is slow and Cusacks character Lloyd is a bit of a doormat Its charming but not perfect
The Good Tier Worth
