John Cusack Movies, Ranked: The 10 Best Films of His 40-Year Career

As an accomplished actor, writer and producer, John Cusack has worked on a lot of projects that he’s incredibly proud of, but he’s still honest with himself about the John Cusack movies that are clunkers. “The ones that suck,” the 57-year-old star has admitted, “I tend to blank out. It's like I never even made them.”

Fans of John Cusack movies would no doubt assure him that the misses have not been as ample as the hits. He’s entertained us from his earliest roles in 1983’s Class and 1984’s Sixteen Candles, through his later work, which has included a role on 2020’s Amazon Prime sci-fi conspiracy thriller series Utopia. For that project, he played biotech specialist Dr. Kevin Christie, who had “almost a sense of a dystopian Willy Wonka to the character,” he said.

The best and most popular John Cusack movies (see our list, below) are sure to never be forgotten by his fans, who revel in watching them over and over.

“It's weird, it's like having your yearbook pictures on cable all the time,” Cusack told Sunday Today of different periods of his life, both personal and professional, being cemented in time for audiences. “It's nice that people still are actually thinking or talking about some of those old movies.”

The 40-year Hollywood veteran can even boast to leaving some fellow celebs speechless at times throughout his career. Brad Pitt recently admitted that he was “starstruck” the first time he saw Cusack right after moving to LA. “I saw John Cusack, and that was the first I had ever seen a man or woman who actually worked in film,” Pitt shared. “It was really strange, being in the same room with someone who you watched on the screen.”

Other A-list celebs were all too eager to sing Cusack’s praises when he earned his star on the Hollywood Walk of Fame more than a decade ago. Dan Aykroyd lauded Cusack for being “the thinking man and thinking woman’s actor, exec producer and writer. Everything that John does has substance,” said the Saturday Night Live legend, who appeared John Cusack movies, 1997’s Grosse Pointe Blank and 2008’s War, Inc.

“Most actors don’t give a crap about other people in the movie,” added Jack Black, who was in 1992’s Bob Roberts, 1999’s Cradle Will Rock and 2000’s High Fidelity with Cusack. “They’re looking out for No. 1. It’s a cutthroat every-man-for-himself kind of biz. That’s why I thank my lucky stars I got to work with such an incredible artist and a class act of a menschy good-stuff potato of a man.”

Not surprisingly, it was John’s sister Joan — “When I'm producing a movie, I know I can get her cheap,” he’s joked — who had the most emotional praise for Cusack, both as an actor and a man. “John is a star. There’s magic in him,” she said, describing her brother as “part It’s a Wonderful Life, part Dr. Strangelove, and part Charlie Brown Christmas.” And, she added of his humble nature, “if you’re lucky enough to be in his sight, [he] will suddenly shorten his 6’3” frame by spreading his feet apart to look you in the eye and make you feel like the star, every time.”

Read on to discover our favorite John Cusack movies that have been highlights of his impressive career.

10. The Grifters (1990)

Never con a con! Roger Ebert raved that “the performances are all insidiously powerful” in this story about a small-time con man (Cusack) and his complicated relationships with two much more experienced grifters, his mother (Anjelica Huston) and his girlfriend (Annette Bening). The role, for which he learned real card and dice tricks from the pros, was “a wonderfully twisted role to dive into,” Cusack said.

9. Better Off Dead… (1995)

In this “abnormal look at a normal teenager,” according to its original trailer, this classic teen-angst title finds Cusack’s character dumped by his girlfriend and depressed, though his attempts to stop his suffering somehow just get increasingly more embarrassing. “It was this surreal teen comedy, and I thought, ‘Wow, when am I going to get a chance to do this again?’ People still really like that film,” Cusack noted to Entertainment Weekly.

8. The Sure Thing (1985)

“Eight o’clock? I don’t know. That’s when I rearrange my sock drawer.” “All the good lines are given to Cusack” as college freshman Gib, according to the Washington Post. This mid-80s Rob Reiner gem “stirs memories of Hollywood’s great classic, It Happened One Night,” added the Associated Press, and Cusack is a standout in one of his earliest lead roles. Daphne Zuniga co-stars as his will-they-or-won’t-they love interest.

7. Eight Men Out (1988)

In this film about the baseball “scandal that broke the heart of a nation,” Cusack had some fun on the job playing Chicago White Sox infielder Buck Weaver, who was involved in helping to throw the 1919 World Series. “I’m a big baseball fan,” Cusack shared. “[Shooting] that was like a childhood dream. I remember going to the old Comiskey [Park] and standing on the same dirt…where Babe Ruth stood. I was taking ground balls and doing batting practice, thinking ‘This is the greatest. I’m totally the luckiest bastard on the face of the earth.’”

6. Grosse Pointe Blank (1997)

“I’m invited to my ten-year high school reunion. What am I gonna say? ‘I killed the president of Paraguay with a fork. How have you been?’” In what MovieWeb calls John Cusack’s “best rom-com,” he plays Martin Blank, an assassin who takes a break back in his hometown, reigniting a relationship with an old flame (Minnie Driver) until work — and a rival (Dan Aykroyd) — start pulling his focus. The black comedy, for which Cusack co-produced and co-wrote the script, “flies on Cusack’s seductive malevolence. He is a marvel,” Rolling Stone raved.

5. Love & Mercy (2014)

“He was a genius, he was ahead of his time,” Cusack said at a 2019 Atlanta event about The Beach Boys’ Brian Wilson, whom he portrays in this engaging biopic. “I’m happy he and [wife] Melinda were happy with the film because it’s his life,” added the actor, who co-stars with Elizabeth Banks as the musician’s manager and wife, Melinda Ledbetter. “The guy who plays me, John Cusack, he's really good. And he sings well,” Wilson told the Houston Press of the good vibrations he got from watching the actor’s portrayal.

4. Bullets Over Broadway (1994)

Cusack shines in Woody Allen’s backstage comedy as a 1920s playwright who makes a deal with the devil — a mob boss — to finance his new project. Jennifer Tilly, Dianne Wiest, Chazz Palminteri, Tracey Ullman, Rob Reiner, and Harvey Fierstein co-star, and Newsweek raved that the way Cusack and the rest of the A-list cast “feast upon their roles is contagious. This is ham cured and roasted to farcical perfection.”

3. High Fidelity (2000)

Esquire not only named this the “truest Chicago movie ever,” but also hometown hero Cusack’s “finest hour.” “I’ll take that compliment,” noted the star and screenplay co-writer of the accolades, and this winning film sure does have a standout cast: Jack Black, Iben Hjejle, Joan Cusack, Todd Louiso, Lisa Bonet, Lili Taylor, Tim Robbins and Catherine Zeta-Jones. The movie —about a struggling record store owner (Cusack) who’s unlucky in love — also not surprisingly has a killer soundtrack.

2. Being John Malkovich (1999)

“It’s my heeeeeead!” It’s hard to stand out in a film titled after one of your co-stars, but Cusack was up for the challenge in this quirky, award-winning cult favorite directed by Spike Jonze. Cusack told The A.V. Club that he went to his agents and said, “Give me the craziest, most unproduceable script you can find,” and the result was this film about a puppeteer who discovers a portal into Malkovich’s mind. It earned Cusack a Best Male Lead nomination at the Independent Spirit Awards, and he and his co-stars (including Cameron Diaz, Catherine Keener and Charlie Sheen) were nominated for a Screen Actors Guild Outstanding Performance by a Cast award as well.

1. Say Anything (1989)

Though you’re probably instantly imagining Peter Gabriel’s “In Your Eyes” playing on a boom box as Cusack’s Lloyd Dobler holds it up over his head so Diane (Ione Skye) could hear it, “There’s a lot of complexity to the film, actually,” Cusack has said. “It might have some of the core of teen films, in that there might be some concessions to the genre, but at the heart of it, it's not a teen movie,” he added of the deeper themes surrounding his character. Still, looking back at its success, he’s not picky about how people choose to remember this beloved classic, even if most people approach him about that boom box scene. “I figure, you know, that's kind of a champagne problem, right? I think if that's as tough as it’s going to get for me, I’m a pretty lucky guy,” Cusack told Sunday Today.

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