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Ranked: The best John Cusack movies of all time

Check out John Cusack's top films

John Cusack headshot
Wikimedia Commons

John Cusack comes from a large family of Hollywood veterans, most notably including his big sister, Joan Cusack. The 80’s lover boy of old turned dramatic actor of late has had quite a durable career. Those who barely know his work would consider him typecasted, playing the same character over and over, or simply portraying his own persona on screen. Those who love and appreciate him, however, might consider him to be one of the best actors in the business, bringing life to every role he signs on for. However you feel about him, there’s no denying that he has been a key player in film history, most particularly the 80’s and leading up to the mid-2000s.

Throughout his career, Cusack has organized theater groups promoting political avant-garde themes and has maintained a surprising dedication to kickboxing, holding a level 6 black belt under world champion Benny Urquidez over a span of 20 years. He also enjoys a casual helicopter snowboarding session from time to time, along with lifelong antiwar activism that shows up even in his music tastes and film choices. Like him or not, Cusack is cemented in history as a true on-screen talent. So, without any further hesitation, these are the 10 best John Cusack movies ranked from least to best!

11. Never Grow Old (2019)

11. Never Grow Old
101m
Genre
Western
Stars
Emile Hirsch, John Cusack, Déborah François
Directed by
Ivan Kavanagh
Watch on Amazon
John Cusack plays against his comedic typecast in this Western film about an outlaw who devastates an old town with a murderous desire for more. Other stellar performances include Emile Hirsch as Patrick Tate. The movie was acclaimed for its setting and directing, too. Sharp dialogue and serene Western landscapes help build a unique yet modern movie within the genre in which Cusack adds maturity and experience after years of honing his craft in Hollywood. Longtime fans and newbies of Cusack’s films should enjoy Never Grow Old.

10. Love & Mercy (2015)

10. Love & Mercy
80%
7.4/10
pg-13
120m
Genre
Drama, Music, History
Stars
Erin Darke, John Cusack, Joanna Going
Directed by
Bill Pohlad
Watch on Amazon
In a masterful biopic of the great Brian Wilson of The Beach Boys, John Cusack and Paul Dano team up to embody the early and late stages of his life, full of turmoil and mental overhaul. Switching between timelines, we witness an adaptation of a younger Brian Wilson as he quits touring to produce the timeless album Pet Sounds, slipping slowly and steadily into psychosis. Cutting to the future, Cusack plays an older and broken Brian Wilson, psychologically limited and trapped under controversial 24-hour therapy tactics from the infamous Dr. Eugene Landy. Beautiful and tragic, we witness the many shattered pieces of Wilson’s psyche as he single-handedly competes with the world-famous Beatles to discover new and experimental music.
Love & Mercy Official Trailer #1 (2015) - Brian Wilson Biopic HD

9. Grosse Pointe Blank (1997)

9. Grosse Pointe Blank
76%
7.3/10
r
107m
Genre
Action, Comedy, Thriller, Romance
Stars
John Cusack, Minnie Driver, Dan Aykroyd
Directed by
George Armitage
Watch on Amazon
Darkly humorous and romantic, Grosse Pointe Blank is a hilarious and delightful film that will undoubtedly go down in history as one of Cusack’s best. Martin Blank (Cusack) is a skilled yet flawed hitman who is back in his hometown of Grosse Pointe, Michigan for a 10-year high school reunion. He meets up with an ex-flame (Minnie Driver) and begins to question the direction of his life as he picks up another assignment in his hometown, simultaneously being hunted by an opposing hitman. This quick-witted action-romance-comedy is excellent for Cusack fans and casual viewers alike, defining a nice slice of a hybrid sub-genre.

8. Better Off Dead... (1985)

8. Better Off Dead...
51%
7.1/10
pg
97m
Genre
Comedy
Stars
John Cusack, David Ogden Stiers, Kim Darby
Directed by
Savage Steve Holland
Watch on Hulu
In zany, cartoony fashion, Better Off Dead is the dark and goofy 80’s comedy that we occasionally crave. Lane Meyer (John Cusack) is a sad young man with a very strange family whose girlfriend recently broke up with him. Because of this, he decides to kill himself, in which the attempts are consistently and accidentally thwarted by his careless friends and family. This black comedy, though a bit silly and inane, is a telling of the imagination of a young man at the end of his rope. Though it may be a bit too corny for some (despite its without-warning surrealism), Cusack makes it endearing with his well-timed deliveries and dramatized self-deprecation.

7. Con Air (1997)

7. Con Air
52%
6.9/10
r
116m
Genre
Action, Thriller, Crime
Stars
Nicolas Cage, John Cusack, John Malkovich
Directed by
Simon West
Watch on Amazon
In one of the best Nicolas Cage movies, Cage stars in the 1997 action thriller Con Air playing the role of Cameron Poe, a former Army Ranger released from prison on parole who can reunite with his wife and daughter. To get to them, he must hitch a ride on a plane filled with Supermax prisoners who plan a coup against the guards and an escape to Mexico. Though Cusack’s role as Agent Vince Larkin would not be considered major, he is essential to the conglomerate of superstars in this film (John Malkovich, Danny Trejo, Dave Chappelle, Steve Buscemi, and more), with unforgettable lines and inflections like, “If you can’t trust a South American drug lord, who can you trust, huh?”
Con Air (1997) Trailer #1 | Movieclips Classic Trailers

6. High Fidelity (2000)

6. High Fidelity
79%
7.4/10
r
113m
Genre
Comedy, Drama, Romance, Music
Stars
John Cusack, Iben Hjejle, Todd Louiso
Directed by
Stephen Frears
Watch on Amazon
Did I listen to pop music because I was miserable? Or was I miserable because I listened to pop music? This Cusack classic is considered by many to be his best film ever, which is telling considering that he had a part in writing the screenplay. Rob (Cusack), is a self-deprecating, self-absorbed, and neurotic music snob/record store owner who revisits his top 5 most memorable breakups, making multitudes of other top 5 lists along the way. Convinced that he is and has been eternally doomed to rejection, he is oblivious to the nearly perfect life he could be living if he would just open his eyes. Loaded with 4th-wall breaks (think Ferris Bueller’s Day Off) where Cusack directly addresses the audience to reinforce his own opinions, this is surely one of his best music films.
High Fidelity (2000) Trailer #1 | Movieclips Classic Trailers

5. The Sure Thing (1985)

5. The Sure Thing
76%
7/10
100m
Genre
Comedy, Romance
Stars
John Cusack, Daphne Zuniga, Anthony Edwards
Directed by
Rob Reiner
Watch on Youtube
“How would you like to have a sexual encounter so intense it could conceivably change your political views?” Another Rob Reiner hit romantic comedy, The Sure Thing, rises above the slew of crude comedies of its time with superior writing and, of course, the comedic timing of John Cusack. When college freshman Walter Gibson (Cusack) is anxious to “get some,” his buddy arranges for him to meet a girl that for sure wants him. The only catch: He has to drive across the country with a classmate Allison (Daphne Zuniga) and his interests begin to change. Lovable and clever as he always is, Cusack turns what could have been just another cheesy rom-com into a comedic ride-along with his fast-talking wit and endearing appeal.

4. Anastasia (1997)

4. Anastasia
61%
7.1/10
94m
Genre
Animation, Family, Fantasy, Adventure
Stars
Meg Ryan, John Cusack, Kelsey Grammer
Directed by
Gary Goldman, Don Bluth
Watch on Disney+

In one of the darkest Disney movies and one of the best movies streaming on Disney+ that would almost surely scar any child, Anastasia tells a tale of royalty and deception through the lens of curse and mystery. When one of the last surviving members of the royal Romanov family, Anastasia (Meg Ryan) is hunted by the evil wizard Rasputin, she must reconnect with her past in order to correct the future. Added for its dark story and a unique setting, this film is a memorable classic in animated cinema, just not recommended for very young children. Cusack’s role as the local scoundrel turned lover boy, though merely a voiceover, is somehow almost as charming as his other performances, showing his true dedication to the craft.

3. The Thin Red Line (1998)

3. The Thin Red Line
78%
7.6/10
r
171m
Genre
Drama, History, War
Stars
Sean Penn, Adrien Brody, Jim Caviezel
Directed by
Terrence Malick
Watch on Amazon
One of the best war movies of all time, The Thin Red Line explores the particular fighting styles and strategies used by the Japanese infantry during their island warfare, where the line between morality and victory was compromised. A reluctant U.S. private (Jim Caviezel) who has chosen to go AWOL is spending time with the locals of a small South Pacific island is soon caught and forced to re-join the ranks to fight the Imperial Japanese Army in WWII. While John Cusack’s role is minor, this movie was remembered in its time for that very reason, as the film deconstructs the role of the protagonist. Not only is this a bold choice for a film, but it captures the chaotic nature of war as the perceived ‘main character’ is nothing more than a soldier in the throes of war.
The Thin Red Line Official Trailer #1 - Terrence Malick Movie (1998)

2. Being John Malkovich (1999)

2. Being John Malkovich
90%
7.8/10
r
113m
Genre
Comedy, Drama, Fantasy
Stars
John Cusack, John Malkovich, Cameron Diaz
Directed by
Spike Jonze
Watch on Amazon
In a conceptual one-off of thematic amalgamation, Spike Jonze’s Being John Malkovich goes into “deep storage” to bring the concept to life. In one of the very first lines delivered in the film, Cusack addresses the audience for the one and only time, “Consciousness is a terrible curse. I think. I feel. I suffer,” which sets the stage for the rest of the film. When a sensitive, dedicated puppeteer named Craig Schwartz (Cusack) is forced to get a real job, he discovers in his very strange office a back room that contains a portal into the mind of John Malkovich. Fantastical and offbeat, this Jonze cinematic wonder is pure escapism, showing what people are willing to do to step out of their own shoes and into another.
Being John Malkovich Official Trailer #1 - John Cusack Movie (1999) HD

1. Say Anything... (1989)

1. Say Anything...
85%
7.3/10
100m
Genre
Romance, Comedy, Drama
Stars
John Cusack, Ione Skye, John Mahoney
Directed by
Cameron Crowe
Watch on Amazon

In a somewhat corny yet wholly genuine 80s fashion, Say Anything is one of the best romantic comedies ever that defines a generation of hopeless romantics with quirky magnificence. A straight-A, bound-for-success high school student (Ione Sky) becomes distracted by the head-over-heels antics of Lloyd (John Cusack), a notorious, kickboxing (also when he became enamored with the art) underachiever who doesn’t know what he wants until he finds love. Wonderfully acted and charming, Cusack really steals the spotlight in this film as the lover boy unapproved by the controlling father, with the forever-epic scene where he blasts the Peter Gabriel classic In Your Eyes from a boombox outside her window. Corny but cool all at the same time, this classic really demonstrates the best parts of a John Cusack movie!

Movie images and data from:
Shawn Laib
Shawn Laib is a freelance writer with publications such as Den of Geek, Quote.com, Edge Media Network, diaTribe, SUPERJUMP…
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