John Cusack’s best films range from teenage romance and sharp comedy to crime, satire, and war drama. This ranking weighs how distinctive his performance is, how central he is to the film, the film’s critical reputation, and what it reveals about his range. It is an editorial order, not a universal verdict: a smaller supporting role can matter as much to a career portrait as a starring performance.
10. The Thin Red Line (1998)
Terrence Malick’s World War II drama is an ensemble film, and Cusack is one part of its large cast rather than its sole focus. That smaller footprint is precisely why it earns a place here: it shows him working in a solemn, contemplative register far removed from the romantic comedies that first made him familiar to audiences. Its scale and reflective approach broaden the picture of his 1990s work.
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![Being John Malkovich (The Criterion Collection) [Blu-ray]](https://m.media-amazon.com/images/I/41z34iZmZXL._SL160_.jpg)
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Being John Malkovich (The Criterion Collection) [Blu-ray] | $32.28 | Buy on Amazon |
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One Crazy Summer | $21.71 | Buy on Amazon |
| 3 |
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1408 | John Cusack, Samuel L. Jackson | $16.90 | Buy on Amazon |
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![2012 (BLU-RAY) - VARIOUS [2009] [Region A & B & C]](https://m.media-amazon.com/images/I/51HqsyKe4BL._SL160_.jpg)
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2012 (BLU-RAY) - VARIOUS [2009] [Region A & B & C] | $26.93 | Buy on Amazon |
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2012 | Buy on Amazon |
9. The Sure Thing (1985)
Before Lloyd in Say Anything, Cusack played another young romantic lead in Rob Reiner’s road comedy. The Sure Thing is an early showcase for his ease with quick, conversational humor and youthful uncertainty. It belongs on a list of his greatest films not because it is the most ambitious entry, but because it captures the comic-romantic mode he would refine into a signature.
8. Eight Men Out (1988)
John Sayles’ baseball drama gives Cusack a place in a serious ensemble story about the 1919 Black Sox scandal. The film expands his early screen identity beyond teen comedy, pairing a period setting with a morally complicated subject. Its value in this ranking is the way it marks a turn toward more varied dramatic work.
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#1 Best Overall
7. Bullets Over Broadway (1994)
In Woody Allen’s backstage comedy, Cusack plays a playwright caught between artistic ambition and the demands of a gangster’s circle. The part asks him to anchor a stylized, fast-moving ensemble without relying on the romantic sincerity of his earlier leads. It is a strong example of his ability to make an anxious, compromised character funny while keeping the stakes legible.
6. The Grifters (1990)
Stephen Frears’ crime drama is a colder, more adult film than Cusack’s youthful romances. He plays Roy Dillon, a small-time con artist entangled in a volatile relationship with his mother and girlfriend. The role’s importance is not only its shift in tone: it places Cusack at the center of a tense story where charm and vulnerability can both be dangerous. Roger Ebert later singled the film out favorably, though one critic’s response is not a measure of consensus.
Rank #2
- One Crazy Summer
5. Grosse Pointe Blank (1997)
Martin Blank is a contract killer returning to his high-school reunion, a premise that lets Cusack combine deadpan comedy with a measure of romantic regret. The film makes a memorable match of his laconic wit and an absurdly violent profession, while giving him a central role in both the comedy and the emotional thread. Ebert’s response was more mixed than his praise for several other Cusack films, a useful reminder that its cult appeal does not mean universal critical agreement.
4. Max (2002)
In Max, Cusack plays an art dealer in post-World War I Munich who encounters a young Adolf Hitler. The historical drama is an unconventional, unsettling entry in his filmography, and its subject matter demands a more restrained performance than his best-known comic roles. It earns its position for the way it tests his range and places him in a morally fraught story rather than a familiar genre vehicle.
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Rank #3
- Blu-ray Movies, Blu-ray TV Shows
3. Say Anything (1989)
Cameron Crowe’s romantic comedy made Lloyd Dobler one of Cusack’s defining screen roles: earnest, funny, and uncertain without becoming a stock ideal boyfriend. The film’s appeal rests on the balance between Lloyd’s confidence and his awkwardness, and Cusack makes both feel like parts of the same person. Say Anything was released April 14, 1989; 20th Century Studios lists it as a 1-hour-53-minute PG-13 comedy/romance written and directed by Crowe, with Ione Skye as Diane. The studio page’s “NOW STREAMING & ON BLU-RAY” label reflects that page when accessed, not guaranteed availability in every location or at all times.
2. High Fidelity (2000)
As Rob, a Chicago used-record-store owner looking back on failed relationships, Cusack turns obsessive taste and self-justification into an unusually involving comic performance. The role’s direct address and quick judgments make the character entertaining, but the film also lets the audience see how Rob’s confidence can disguise immaturity. Roger Ebert described it as a comedy about pop-music obsession and relationships. Cusack received a Golden Globe nomination for the film in 2001, and Ebert gave it especially favorable attention.
1. Being John Malkovich (1999)
Spike Jonze’s surreal comedy gives Cusack one of his most distinctive leading roles: Craig Schwartz, a struggling puppeteer who discovers a portal into the mind of actor John Malkovich. Cusack plays Craig’s ambition and insecurity as comic, uncomfortable, and increasingly unsettling, anchoring a premise that could easily float away from its characters. It is the clearest meeting point between his screen presence and a film willing to take a genuinely strange creative risk. In a 2007 interview with Guardian journalist Ryan Gilbey, Cusack said: “Being John Malkovich worked out great, so people tend to forget what a risk it was – first-time writer, first-time director and so on.” He received an Independent Spirit Award nomination in the Best Actor category for the film, and Roger Ebert also responded especially favorably to it.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Why these ten, and what nearly made the list
This selection favors a balance of central performances and films that reveal a different side of Cusack. That means the ranking is not simply a list of his biggest lead roles: The Thin Red Line matters as an ensemble contribution, while The Grifters, Max, and Being John Malkovich show how far his work moved from the teen and romantic-comedy image of his early career.
Best Value
Love & Mercy is a notable close call, alongside later-period genre titles such as 1408, 2012, and Grand Piano. Rotten Tomatoes’ 2022 career guide highlights these as part of a filmography that spans romance, drama, comedy, and genre work. Cusack’s own 2007 list of ten good films included The Sure Thing, Eight Men Out, Say Anything, The Grifters, Bullets Over Broadway, Grosse Pointe Blank, The Thin Red Line, Being John Malkovich, High Fidelity, and Max. That is valuable context from the actor, not a definitive ranking or an up-to-date list of the only films worth watching.
Quick Recap
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