20. The Journey of Natty Gann (1985)

It’s the Great Depression à la Disney when a tomboy, Natty, rides the rails in search of her lumberjack father. This marked the first time I saw Cusack, impressive as a wise young hobo, though not the first time I saw Natty’s wolf-dog companion: it’s Jed, sled-dog from The Thing!

19. Tapeheads (1988)

Mike Nesmith of the Monkees produced this goofy 1980s-tastic slapstick comedy with a cult supporting cast and top-notch soundtrack. Cusack (sporting a sleazy tache) and Tim Robbins play losers whose rock video company prospers in the wake of a Skylab-related tragedy.

18. High Fidelity (2000)

Cusack temporarily reverts to a teen movie persona, but is too cool to be convincing as the list-compiling manchild of Nick Hornby’s novel, transposed to Chicago. If you don’t mind women depicted as killjoys with poor taste in music, the portrayal of commitment-phobic masculinity with a gatekeeping approach to pop culture is breezy, shallow fun.

17. Max (2002)

In 1918 Munich, Cusack plays a Jewish gallery owner who indulges the artistic aspirations of a disgruntled army veteran (Noah Taylor) with a talent for antisemitic oration. This Hitler origin story needed more Ken Russell-type flamboyance, despite some eye-popping performance art in which one-armed Cusack sinks naked into a giant meat grinder.

16. Say Anything … (1989)

Just before graduating to grownup characters, Cusack dipped into teenage romcom one last time for Cameron Crowe’s directing debut. Lloyd Dobler is a slacker who falls for the cleverest girl in school. Their on-again-off-again romance features that iconic courtship-by-boombox scene, as well as super supporting turns from Lili Taylor and Cusack’s sister Joan.

15. Con Air (1997)

In between outrageous hamming from the likes of John Malkovich and Ving Rhames as convicts who hijack their plane, Cusack fills the onlooker role as an understandably sweaty US marshal. Nicolas Cage plays the heroic prisoner on parole who must thwart the psychos in a dopey-but-diverting action-fest.

14. Fat Man and Little Boy (1989)

Paul Newman stars as General Groves (played by Matt Damon in Oppenheimer), assigned to oversee development of the first atom bomb. But it’s Cusack who haunts the memory as a (fictional) scientist who suffers the consequences of a lab mishap. “Everybody should make it,” he says after doing some maths, “except me. I’m going to die.”

13. Bullets Over Broadway (1994)

As the Woody Allen surrogate in one of the Woodster’s funnier post-Farrow comedies, set in 1920s New York, Cusack is a playwright who gets his production financed by casting a gangster’s moll – only to find her mobster bodyguard is a better writer than he is. Oscar-winning Dianne Wiest is a hoot as an alcoholic actress. “Don’t speak!”

12. The Sure Thing (1985)

Before filling a small role in Rob Reiner’s Stand By Me, Cusack starred in the same director’s smashing teen variation on It Happened One Night. “Gib” Gibson is a beer-swilling slob whose plan to have sex with a California hottie gets sidetracked when he shares a cross-country ride with a buttoned-up fellow student.

11. Eight Men Out (1988)

John Sayles’ meticulous period drama is a useful primer on the Chicago Black Sox scandal, a key reference in American pop culture. A clutch of baseball players, aggrieved by management’s refusal to award a deserved bonus, agree to throw the 1919 World Series. In a stacked ensemble cast, Cusack tackles one of his first adult roles as the luckless shortstop, Buck Weaver.

10. 2012 (2009)

Can sci-fi novelist Cusack reunite with his wife before director Roland Emmerich trashes the planet with solar flares, tsunamis and volcanic eruptions? Naturally, the billionaires have hatched a plan to survive this disaster movie with a body count in the zillions. It’s just a pity they don’t all meet the fate of Cusack’s love rival, killed off in the most sadistic way possible.

9. The Paperboy (2012)

This deranged slice of southern gothic is best known for Nicole Kidman peeing on Zac Efron’s jellyfish stings, but Cusack lets it all hang out as a swamp-dwelling, alligator-hunting racist creep with a sad Nic Cage hairdo. You’ve never lived until you’ve seen Kidman bringing him to orgasm in the prison visiting room!

8. Grand Piano (2013)

A neurotic pianist (Elijah Wood) gets a message saying “Play one wrong note and you die” during a concert. Cusack exudes smarmy menace in a mainly voice role as the bad guy in this preposterous thriller. Eugenio Mira is evidently incapable of directing a single scene of Damien Chazelle’s screenplay without doing something adorably bonkers with it.

7. Identity (2003)

Ten people, stranded by a rainstorm at a remote Nevada motel, are murdered, one by one, in James Mangold’s And Then There Were None-ish psycho-thriller. Cusack plays a Sartre-reading ex-cop who tries to solve the mystery and stumbles across a plot twist that enraged me on first viewing, but proved lots more fun on a rewatch.

6. Maps to the Stars (2014)

Deep into his villain phase, Cusack is chilling as a celebrity therapist for whom karma looms in the form of his pyromaniac daughter, in Los Angeles to confront her family and its dark secrets. David Cronenberg takes no prisoners in his grim but great Hollywood satire; Julianne Moore gives a fearless performance as a drug-addled film star with constipation.

5. Love & Mercy (2014)

This non-linear Brian Wilson biopic interweaves Paul Dano as 1960s Wilson with Cusack as the heavily medicated 1980s incarnation. In the 1960s, he’s revolutionising pop music with inspired tinkering in the studio, but already struggling with mental illness. In the 1980s, he’s in thrall to 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 must wrestle 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 virtually a one-man show for Cusack, who rises to the occasion with a virtuoso display of scepticism dissolving into paranoia and yelling at the fridge.

3. Grosse Point 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 larky, but there are dark hints about the moral relativism of modern America, and Cusack embodies the art of deadpan cool.

2. The Grifters (1990)

Cusack definitively left teen movies behind with his performance as a cute but shifty 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, Annette Bening 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 ball exploring his dark side as a peevish street puppeteer who discovers a secret portal into the mind of the actor John Malkovich. That’s just the start of Charlie Kaufman’s endlessly inventive scenario that stirs questions of identity, sexuality and control into a surreal cocktail, enhanced by a matter-of-fact mise en scène that avoids swishy special effects.