John Cusack was a powerhouse force in Hollywood, seamlessly transitioning from a boombox-wielding lover boy of the ‘80s to an esteemed dramatic actor. His impressive and colorful acting resume features an assortment of unique and prominent films and characters, spanning back to his big screen breakout role in 1985’s The Sure Thing. Since first gaining a reputation as a talented and slightly offbeat performer, Cusack’s star only got shined brighter for the next two decades. He hails from a family of gifted actors, including his equally dynamic and endearing big sister Joan.

Updated August 2022: We love John Cusack, so in order to keep our list of his best movie performances up to snuff, we've updated this article to maintain our high degree of consistency and standards of excellence.

Perhaps the most refreshing attribute Cusack possesses is his desire to do it all, from the teen comedy of Sixteen Candles to the gritty Western of Never Grow Old; over the years he has appeared in a wide array of diverse genres, never sticking to the status quo. His eccentric characters are memorable and intriguing and leave lasting impressions for moviegoers. Whether he’s portraying an assassin with second thoughts, a paranormal debunker or a puppeteer with an affinity for John Malkovich, Cusack has undoubtedly cemented his status in cinema history, even if (as he admits) he no longer has the box office draw he once held. Let’s take a look at the best John Cusack movies.

13 Anastasia

Loosely based on the legend of the Grand Duchess Anastasia, 1997’s animated musical film Anastasia features a talented voice cast with big name stars including Meg Ryan, John Cusack, Kelsey Grammer, and Christopher Lloyd. The stunning fantasy follows 18-year-old amnesiac Anastasia “Anya” Romanov (Ryan) as she joins two con-men on her quest to be reunited with her beloved grandmother, the Dowager Empress. Unbeknownst to the trio, the undead Rasputin is also after Anastasia and seeks her death.

Cusack voices young con-man Dimitri, who was once a servant to the Romanovs and is Anastasia’s love interest. Upon its release, the film earned rave reviews for its voice performances, music, and animation, and also inspired a stage musical, spin-off film and countless merchandise. Today, it's recognized as one of the most mature and best animated movies of the '90s.

12 1408

1408, the 2007 psychological horror flick based on the Stephen King story, follows a man who specializes in debunking paranormal occurrences. John Cusack stars as Mike Enslin, who rents the fabled room 1408 at the Dolphin Hotel and soon finds himself trapped in the room where he is ultimately confronted with absolute terror. Co-starring Samuel L. Jackson as the sinister hotel’s manager Gerald Olin, 1408 is a creepy thriller that is downright horrifying in both concept and execution.

The film earned mainly positive reviews and was a box office success, with many critics praising Cusack’s performance and considered the picture to be superior to other Stephen King adaptations. Esteemed critic James Berardinelli singled out Cusack’s powerful performance, writing that “this is John Cusack’s movie to carry, and he has no problem taking it where it needs to go.”

11 The Ice Harvest

A cold, cruel, and comical dark thriller, The Ice Harvest remains one of the darkest Christmas movies ever made. The film chronicles Charlie (Cusack) and Vic (Billy Bob Thornton) in Wichita, Kansas on a freezing Christmas Eve as the two scheme to steal a great deal of money from a dangerous man. Oliver Platt and Connie Nielsen also star in this wicked dark comedy, one of the great cold-blooded neo-noirs of modern times.

10 The Sure Thing

Esteemed director Rob Reiner’s 1985 adventure rom-com The Sure Thing chronicles the cross-country adventure college students Walter and Alison embark on in search of their ideal match. Featuring John Cusack and Daphne Zuniga as classmates who inadvertently become each other’s foil, the film centers on Walter’s quest to meet a “sure thing” that is waiting in California for him.

Related: The Best Coming-Of-Age Films of the '80s

Director Rob Reiner initially refused to see the actor since he was under-age, but after his audition he knew Cusack was perfect for the role. Since Cusack was actually only 16 at the time of production, he had to go to court in order to be emancipated and be allowed to film the long hours. The Sure Thing was considered the actor’s breakout role and was a modest success both critically and financially.

9 Max

The criminally underrated and haunting film Max speculates how much history would have changed if the monstrous Adolf Hitler was encouraged in his artistic endeavors rather than his political career. The film chronicles the relationship between a young Hitler and the titular Max Rothman (John Cusack), both of whom had come back wounded and depressed from Germany's defeat in World War I. Rothman opens an art gallery and encourages Hitler to pursue his drawing (especially architecturally), justifiably fearing what would happen if Hitler followed his political skills instead. Max is ultimately a tragic and painful film but an important one, and Cusack delivers one of the most subtle and brilliant performances of his career.

8 Runaway Jury

The 2003 legal thriller Runaway Jury, an adaptation of the John Grisham novel, centers on a juror on the inside and woman on the outside as they manipulate a court trial involving a major gun manufacturer. John Cusack and Rachel Weisz star as the couple with the gift of swaying juries, with Dustin Hoffman and Gene Hackman portraying a determined lawyer and shady jury consultant, respectively.

Runaway Jury earned critical praise upon its release, earning compliments for its many twists and turns and riveting storytelling, such as the unique concept of selling the jury to the highest-bidding party. The talented cast and thrilling cat-and-mouse premise helps make the movie a gripping and dramatic ride for audiences.

7 Bullets Over Broadway

Hollywood heavyweight Woody Allen directed the 1994 dark comedy crime flick Bullets Over Broadway, which features an impressive A-list ensemble cast including John Cusack, Dianne Wiest, Jennifer Tilly, and Chazz Palminteri. Set in New York in 1928, the movie centers on a struggling playwright (Cusack) who is forced to cast a mobster’s talentless girlfriend in his latest drama if he hopes to see it produced.

Widely considered one of Allen’s greatest works of the past three decades, Bullets Over Broadway is a backstage farce with sharp dialogue and direction and star-making performances by its leads. The film was nominated for seven Academy Awards, with Wiest winning for Best Supporting Actress, and currently holds a 97% rating on Rotten Tomatoes.

6 Better Off Dead

A vastly underrated '80s teen comedy, Better Off Dead is a truly bonkers film from Savage Steve Holland (who also directed Cusack in the great One Crazy Summer). The movie follows Lane Myer (Cusack) as he navigates his suburban life after his girlfriend dumps him for the captain of the ski team. Lane teams up with his silent foreign exchange student neighbor and zonked-out best friend (Curtis Armstrong, never better) to learn how to ski, and along the way there are vengeance-seeking paperboys, sentient Jell-O, snow-snorting, dancing hamburgers, space shuttles, and more in this absurdist classic.

5 Con Air

Nicolas Cage and John Cusack join forces for the action thriller Con Air, in which Cage stars as just-paroled army ranger Cameron Poe, who must fly home on board a prison transport. Cusack portrays U.S. Marshal Vince Larkin, who enlists Poe’s help when a violent escape plot unfolds mid-flight by some of the country’s worst criminals.

With John Malkovich, Ving Rhames, and Steve Buscemi rounding out the impressive cast, Con Air is jam-packed with powerhouse performances and explosive action that takes moviegoers on a wild, intense ride. The thriller was a box office hit, earning $224 million and garnering praise for its strong cast and blood-pumping action sequences. The big budget extravaganza is every action film junkie’s ultimate flick and doesn’t take itself too seriously, only adding to the excitement and thrills.

4 Grosse Pointe Blank

Grosse Pointe Blank, the 1997 dark comedy masterpiece written by Steve Pink, finds John Cusack as professional assassin Martin Blank, who returns to his hometown to attend his high school reunion and complete a high-stakes mission. Along the way, Martin reconnects with an old flame (the lovely Minnie Driver) and begins to question the direction his life has gone in. He is also being pursued by an opposing hitman (the always hilarious Dan Aykroyd) which makes his big homecoming all the more complicated and entertaining.

Grosse Pointe Blank is an off-the-wall comedy that is also effortlessly cool and full of laughs, delightful dark humor, and dialogue that packs a punch. Cusack shines in the comedic role and is a bona fide sex symbol in the film, with Peter Travers of Rolling Stone proclaiming the actor a marvel and that the film “flies on Cusack’s seductive malevolence.”

3 High Fidelity

The classic Cusack film High Fidelity is considered to be one of the actor’s finest flicks, and follows failed record store owner Rob Gordon (Cusack) as he hilariously recounts his top five breakups, even the one currently in progress. Based on the 1995 Nick Hornby British novel, Cusack co-wrote the screenplay and found his biggest challenge with the adaptation was breaking the fourth wall and talking directly to the audience.

Related: Explained: Here's How the High Fidelity Movie Affected the Rom-Com Genre

Hollywood then-up-and-comer Jack Black, Catherine Zeta-Jones, and Lisa Bonet also co-star in the entertaining, romantic film which garnered rave reviews, earning praise for the entertaining story, gifted cast and epic soundtrack. Cusack’s performance was applauded, with The New York Times declaring that the actor was “a master at projecting easygoing camaraderie, he navigates the transitions with such an astonishing naturalness and fluency that you’re almost unaware of them.”

2 Say Anything…

Ultimate romantic teen comedy Say Anything… is the directorial debut of Hollywood great Cameron Crowe, and depicts the romance between devoted underachiever Lloyd and beautiful valedictorian Diane after their high school graduation. The 1989 cult classic is the quintessential ‘80s flick, and features a memorable performance by John Cusack. He steals the show as the endearing underdog boyfriend, combating Diane’s controlling father and never giving up on the epic love he feels for his girlfriend. It’s impossible to forget the iconic scene in which Cusack blasts the Peter Gabriel hit “In Your Eyes” from a large boombox outside her bedroom window, though the entire film is good enough to warrant a 98% score from critics on Rotten Tomatoes.

1 Being John Malkovich

Undeniably one of the most unique and pleasantly bizarre films to grace the silver screen is the Spike Jonze-directed fantasy comedy Being John Malkovich. The 1999 cinema spectacle features a gifted cast including John Cusack, Cameron Diaz, Catherine Keener, and John Malkovich as a satirical version of himself. Cusack stars as a puppeteer who discovers a portal that leads directly into the mind of Malkovich, in Charlie Kaufman's brilliant script.

The offbeat and fantastically funny comedy is director Spike Jonze at his finest, and its very meta premise truly takes moviegoers on a wild and engrossing journey. The film was widely acclaimed by critics, with Entertainment Weekly calling it “the most excitingly original movie of the year.” John Cusack effortlessly embraces the weird and eccentric role and delivers a dynamite performance in the process, proving why he's one of the best.