24 Classic John Cusack Movies Everyone Will Love

John Cusack has enjoyed a career that any performer would envy. It’s not just his longevity but also the range of parts he’s played. From his beginnings when Cusack starred in off-beat teen comedies to his most recent work in action movies produced overseas, Cusack has over 75 film credits to his name.

These John Cusack movies include some of the best films of the past few decades. They include his works with famed filmmakers such as Spike Lee and Terrance Malick, as well as other first-class auteurs.

1. Grosse Pointe Blank (1997)

Produced among the boom of flashy crime movies that proliferated after the success of Pulp Fiction, Grosse Pointe Blank could have been another slick but soulless Quentin Tarantino knock-off. However, director George Armitage — working off a screenplay by Tom Jankiewicz and D. V. DeVincentis, revised by Cusack and Steve Pink — created a more thoughtful and sweet movie.

Armitage makes good use of the sense of reserve that Cusack brings to his characters, allowing him to play a hitman Martin Blank as a man whose existential crisis brings him back to his Michigan hometown in time for a high school reunion.

2. Being John Malkovich (1999)

Cusack has played plenty of weirdos in his career, but he rarely allowed himself to portray someone as off-putting as the embittered puppeteer Craig Schwartz in Being John Malkovich. Written by Charlie Kaufman and directed by Spike Jonez, the surreal Being John Malkovich involves a mysterious portal that allows anyone who goes through it to enter the mind of the titular actor.

Cusack’s fearless take has no interest in winning the audience’s sympathies, which leaves viewers to wrestle with the movie’s strange premise. Though Malkovich gets his name in the title, it remains one of the defining John Cusack movies.

3. Say Anything… (1989)

Writer and director Cameron Crowe wasn’t the first person to cast Cusack in a teen comedy. But with Say Anything…, Crowe found the perfect vehicle for young Cusack’s unorthodox charm.

Protagonist Lloyd Dobbler, an idealistic kickboxer, could have been a stereotypical romantic loner who pursues the beautiful valedictorian Diane (Ione Skye). But Cusack invites the audience to doubt Dobbler’s grand pronouncements, making the teen into something richer and more realistic.

4. Love & Mercy (2014)

On paper, Cusack seems an odd choice to play Beach Boys member Brian Wilson in the biopic Love & Mercy, directed by Bill Pohlad and written by Oren Moverman and Michael Alan Lerner. Paul Dano, who portrays Wilson in his 1960s heyday.

Cusack resembles neither Dano nor the real Wilson, but he brings a moving nervous energy to playing the rocker in his 40s, over-medicated and under the control of the abusive Dr. Landy (Paul Giamatti). Cusack emphasizes the vulnerability of Wilson during this period, which drives his romance with Melinda Ledbetter (Elizabeth Banks) and leads to the rediscovery of his musical talent.

5. High Fidelity (2000)

In the wrong hands, the morose record store clerk Rob Gordon would be unbearable, an arrogant nerd who lacks the self-awareness to see how he treats other people with disrespect.

And yet, director Stephen Frears, along with Cusack and his usual team of co-writers — D. V. DeVincentis, Steve Pink, and Scott Rosenberg — show viewers the flaws that Rob refuses to acknowledge. Adapting the novel by Nick Hornby, High Fidelity tracks Rob’s reluctant transformation from a cynical critic to someone who can care about people — a little bit, anyway.

6. Better Off Dead (1985)

Before the heartfelt Say Anything…, Cusack made his name in wacky teen comedies from writer and director Savage Steve Holland, starting with Better Off Dead.

When teen Lane Myer (Cusack) gets dumped by his girlfriend Beth (Amanda Wyss), he tries to waver between foolhardy plots and deep despair. The cycle breaks when Lane meets French foreign exchange student Monique Junot (Diane Franklin), who helps him train to ski a black diamond and win back Beth’s heart.

Better Off Dead doesn’t have the most compelling plot in the world, but Holland’s zany approach sets it apart from other entries in the genre, brought to life by a game Cusack.

7. Grace is Gone (2007)

In his most famous roles, Cusack plays characters who cover their vulnerability with a thin veneer of cool. In Grace is Gone by writer and director James C. Strouse, Cusack applies that same approach to a sensitive drama.

Upon learning that his wife Grace died in combat, Army veteran Stanley Phillips (Cusack) avoids telling his daughters to prolong their happiness as long as possible. While Grace is Gone has much higher stakes than Cusack’s other roles, the story functions much like those previous comedies, as Stanley struggles to present himself as a carefree father, despite the tremendous sorrow he feels.

8. 1408 (2007)

Directed by Mikael Håfström and written by Matt Greenberg, Scott Alexander, and Larry Karaszewski, 1408 turns the Stephen King short story into a claustrophobic horror film. Cusack plays skeptical author Mike Enslin, who visits a haunted hotel room to debunk its legend. Mike ignores the warnings of the hotel manager (Samuel L. Jackson) and stays in the room, which does indeed prove to host spirits. Although Håfström includes plenty of scares in his depiction of Mike’s haunted hotel stay, the movie’s real power comes from his reaction to the trauma the ghosts force him to face, giving Cusack depths to play in what could have been a one-note horror victim.

9. The Thin Red Line (1998)

As the first movie the great Terrance Malick made after a two-decade absence, The Thin Red Line drew an all-star cast, including George Clooney, Nick Nolte, Woody Harrelson, and more.

Despite the big names involved, the ever-idiosyncratic Malick followed his own whims while adapting author James Jones’s novel about World War II. Malick trimmed appearances by major actors to mere cameos. Cusack’s Captain John Gaff mostly makes the cut, in which he leads he plays an overwhelmed leader in the movie’s most action-packed sequence, guiding his fellow troops to take a contested hill.

10. War, Inc. (2008)

Together with Say Anything… and Grosse Pointe Blank, War, Inc. completes a loose trilogy of films about the ongoing destruction wrought by the American military-industrial complex. Cusack’s War, Inc. character Brand Hauser, a hitman with CIA connections, feels like an older and more cynical version of Lloyd Dobbler or Martin Blank.

An outrageous comedy directed by Joshua Seftel and written by Cusack, Jeremy Pikser, and postmodern author Mark Leyner, War, Inc. takes broad shots at the relationship between the media, capitalism, and the Iraq War. It may not have the heart of some of Cusack’s other movies, but War, Inc. attacks its subject with a soldier’s viciousness.

11. The Grifters (1990)

In The Grifters, his first collaboration with director Stephen Frears, Cusack plays Roy Dillon, a small-time con man with big ambitions. Roy’s plans bring him into the orbit of grifter Myra (Annette Benning) and his mother Lilly (Angelica Huston), an old pro who works for the dangerous gangster Bobo Justus (Pat Hingle).

As Roy tries to prove himself to Lilly and win over Myra, he gets pulled deeper into the criminal’s dangerous game. The script by veteran crime writer Donald E. Westlake, adapting the novel by Jim Thompson, creates a frightening world, in which acts of cruelty lie behind every deal and scam. Of all the John Cusack movies mentioned here, this one will have most viewers on the edge of their seat.

12. Runaway Jury (2003)

By 2003, Cusack had outworn much of the cool that made him a teen movie star in the 1980s. However, he still had a gift for playing slick fast-talkers, as demonstrated in the John Grisham adaptation Runaway Jury, directed by Gary Fleder and written by Brian Koppelman, David Levien, Rick Cleveland, and Matthew Chapman.

When viewers first meet Cusack’s Nick Easter, he seems just like another likable schlub who gets roped into serving on a jury. However, Nick and his partner (Rachel Weisz) are much more than they appear, much to the chagrin of powerful consultant Rankin Fitch (Gene Hackman).

13. The Ice Harvest (2005)

Don’t be fooled by the Christmas Eve setting. Director Harold Ramis’s The Ice Harvest has no interest in peace on Earth or goodwill toward men, as the script by Richard Russo and Robert Benton, adapting a novel by Scott Phillips, has a heart as cold as the snow that covers the ground.

Cusack stars alongside Billy Bob Thornton as a couple of lowlife crooks who swipe $2 million from their gangster boss (Randy Quaid). The duo’s getaway hits a snag when an ice storm forces them to stay in town, hoping to lay low until the road clears up. Of course, it doesn’t go well, forcing the cynical characters to make selfish choice after selfish choice.

14. Tapeheads (1988)

Tapeheads shares a lot of DNA with UHF, and not just because Weird Al Yankovich makes an appearance. Director Bill Fishman, who co-wrote the script with Peter McCarthy, cuts often to wacky video clips, including an over-the-top rap song promoting a greasy chicken joint.

But where UHF stayed in the world of low-budget TV, Tapeheads takes place in the music industry, where would-be big shots Ivan (Cusack) and Josh (Tim Robbins) hope to make their name. Fishman pushes the material to almost cartoonish heights, but Cusack and Robbins follow suit, embracing their slimeball characters and poking fun at arrogant rock stars.

15. America’s Sweethearts (2001)

One might assume that Cusack wouldn’t have to work too hard to play Eddie Thomas, the Hollywood actor he portrays in the comedy America’s Sweethearts, directed by Joe Roth and written by Susan Arnold, Billy Crystal, and Donna Arkoff Roth. However, Cusack uses his familiarity with the business to make Eddie into a neurotic weirdo, something more interesting than the standard movie star.

Cusack’s approach to Eddie heightens the comedy of his relationship with girlfriend and fellow actor Gwen (Catherine Zeta-Jones) and harried publicist Kiki (Julia Roberts).

16. Maps to the Stars (2014)

Where America’s Sweethearts poked fun at the Hollywood elite, Maps to the Stars eviscerates Tinseltown without mercy. One would expect nothing less from director David Cronenberg, working from a script by Bruce Wagner. Cusack appears in the dyspeptic look at the movie business as dyspeptic Stafford Weiss, father of the child star Benjie (Evan Bird).

Quick to offer empty bromides and slow to self-reflection, Stafford sees himself as too enlightened to fall for the same problems that snared actress Havana Segrand (Julianne Moore) or hopeful Jerome Fontana (Robert Pattinson). But in Maps to the Stars, no one escapes the Hollywood trap, least of all people like Stafford Weiss.

17. Identity (2003)

While Cusack has more than a few prestige pictures to his name, he wasn’t above doing fun schlock, not even in the 2000s. Case in point, the psychological horror thriller Identity, directed by James Mangold and written by Michael Cooney. Limousine driver Ed Dakota (Cusack) must recall the investigative skills he developed as a police officer when he finds himself stranded at a motel with a group of strangers, who begin dying one by one.

Despite its lowbrow subject matter, Cusack has fun with the role, and even finds surprising depths to play, especially as the movie builds to its twist ending.

18. The Road to Wellville (1994)

The T.C. Boyle novel The Road to Wellville may be about a real person, cereal founder and medical quack W.K. Kellogg, and a real place, the Kellogg Sanitarium in Michigan, but writer/director Alan Parker has no interest in realism. Driven by Anthony Hopkins’s goofy take on Kellogg, The Road to Wellville pokes fun at the ridiculous lengths to which upper-class people go in pursuit of health.

Cusack’s schemer Charles Ossining, who wants to create a competitor to Kellogg’s Corn Flakes, doesn’t get quite as silly as other plots in the film, but it still shows humanity at its most desperate.

19. Chi-Raq (2015)

The Spike Lee movie Chi-Raq draws its inspiration from the ancient Greek play Lysistrata by Aristophanes, in which women refuse to couple with any men until the Peloponnesian War comes to an end. However, Lee and co-writer Kevin Willmott take a modern approach to the subject matter, imagining Lysistrata (Teyonah Parris) as a Chicago citizen committed to ending gang violence in her town.

Cusack appears in Chi-Raq as street preacher Mike Corridan, whose fiery sermons help inspire Lysistrata to stay the course.

20. One Crazy Summer (1986)

In his second collaboration with writer and director Savage Steve Holland, Cusack plays floundering high school grad Hoops McCann. Like Better Off Dead, One Crazy Summer takes regular diversions into skits and animation set-pieces.

When it gets down to the business of Hoops romance with rocker Cassandra Eldridge (Demi Moore), One Crazy Summer loses some steam, as the leads don’t gel quite as well as Cusack and Diane Franklin in Better Off Dead. But during the more antic sequences, Cusack reminds viewers why he and Holland made such a good pair.

21. Con Air (1997)

Producer Jerry Bruckheimer knows how to assemble overqualified casts for mindless action flicks, and Con Air is no exception. Directed by Simon West and written by Cusack’s frequent collaborator Scott Rosenberg, Con Air stars Nicolas Cage as a good man sentenced to prison for manslaughter, who finds himself stuck in a criminal plot to hijack an airplane.

Cusack plays a cocky U.S. Marshall agent who supports Cage’s Cameron Poe from the ground, hoping to contain the serial killers Cyrus “the Virus” Grissom (John Malkovich) and Garland “The Marietta Mangler” Greene (Steve Buscemi). Cusack and the others have fun with the wild premise, making for an enjoyable brainless romp.

22. Serendipity (2001)

Although he had done many romantic movies during his 1980s run, but they most often took the form of wacky comedies, lacking the sincerity of Serendipity. Directed by Peter Chelsom, Serendipity stars Cusack as a producer Jonathan, who reunites with Sara (Kate Beckinsale), a woman with whom he had a chain of chance meetings years earlier.

The script by Marc Klein hits the expected genre beats, but Cusack and Beckinsale play them straight without winking at the audience, making the movie feel warm and inviting.

23. The Journey of Natty Gann (1985)

While Cusack spent most of the 1980s making racy teen romps, he did play a supporting part in the Disney adventure film The Journey of Natty Gann, written by Jeanne Rosenberg and directed by Jeremy Kagan.

Set during the Great Depression, The Journey of Natty Gann stars Meredith Salenger as a girl who rides the rails to find her father (Ray Wise), sent across the country looking for work. Cusack shows up as Harry, an older boy who travels with hobos and takes a liking to Natty. The part affords Cusack fewer opportunities to play a comic lead, but it lets him show off the dramatic chops that will become key parts of his career.

24. The Sure Thing (1985)

“Okay, it’s stupid,” declares Cusack’s character Walter Gibson in The Sure Thing. “What’s wrong with that?” Within the movie, Gibson makes this argument to his classmate Allison (Daphne Zuniga) when he laughs about getting mooned by a passing motorist. But it could also serve as a defense of The Sure Thing, directed by Rob Reiner and written by Steven L. Bloom and Jonathan Roberts.

The Sure Thing follows the same plot beats as most teen comedies of the era, in which a young man pursues physical relations, just to fall for the wholesome girl who was always by his side. But along the way, the movie indulges in a lot of stupid behavior, trying desperately to convince viewers to laugh along with it.