John Cusack stands out in Hollywood as an unconventional hero, much like the characters he often portrays. Shunning the typical trappings of fame and formulaic films, Cusack has carved a unique and respected career by consistently choosing roles that highlight underdogs and outsiders. All the while, he has largely managed to stay out of the intense glare of the media spotlight, letting his work speak for itself.
Born in Evanston, Illinois, John Cusack hails from a thoroughly show business-oriented Irish-American family. While his mother Nancy (née Carolan) was a math teacher, his father Dick Cusack was an actor and filmmaker, setting the stage for a family legacy in entertainment. John’s siblings, Joan Cusack, Ann Cusack, Bill Cusack, and Susie Cusack, all followed in their father’s footsteps, establishing themselves as accomplished actors. This familial environment immersed John in the world of performance from a young age. Like his siblings, John joined Chicago’s Piven Theatre Workshop while still in elementary school, gaining invaluable early experience. By the age of twelve, he had already amassed an impressive resume that included stage productions, commercial voice-overs, and industrial films. This early immersion into acting provided a solid foundation for his future film career.
His feature film debut came at the age of 17 in the romantic comedy Class (1983), where he appeared alongside Rob Lowe and Andrew McCarthy. This initial role marked the beginning of his transition into film. Following this, Cusack secured a role in Sixteen Candles (1984) as part of Anthony Michael Hall’s “geek brigade,” a role that initially positioned him within the teen movie genre.
John Cusack gained early recognition in teen films like Sixteen Candles.
However, Cusack remained somewhat on the fringes of the Brat Pack phenomenon. While many of his contemporaries experienced rapid but often fleeting fame, Cusack opted for a different path. He consistently worked, securing lead roles in films such as The Sure Thing (1985) and Better Off Dead (1985). These roles showcased his ability to handle comedic and romantic elements, solidifying his presence in the coming-of-age movie landscape. For many, young Cusack is perhaps most fondly remembered for what could be considered his quintessential adolescent role: Lloyd Dobler, the romantic and determined protagonist in Say Anything… (1989), famously known for holding a boombox aloft playing Peter Gabriel. This role became iconic and remains one of the most beloved John Cusack Movies.
Say Anything… (1989) is considered one of the most iconic John Cusack movies, featuring his memorable portrayal of Lloyd Dobler.
A year later, Cusack transitioned into more mature roles, starring in The Grifters (1990). In this film, he portrayed a small-time con artist caught between his manipulative mother and his strong-willed girlfriend, demonstrating his range and ability to tackle darker, more complex characters. This marked a significant shift from his teen movie roles and indicated his desire to explore diverse and challenging projects.
The subsequent years saw Cusack exploring projects beyond acting, revealing his multifaceted talents. He directed and produced several shows for The New Criminals, a Chicago-based theater group he founded in 1988. Inspired by Tim Robbins’ Actors’ Gang in Los Angeles, The New Criminals aimed to promote politically engaged and avant-garde theater. Expanding his creative endeavors, Cusack, along with high school friends Steve Pink and D.V. DeVincentis, established a sister company for film in 1992 named New Crime Productions. This move demonstrated his commitment to fostering independent and innovative filmmaking.
New Crime Productions’ first feature film was Grosse Pointe Blank (1997), a sharply written dark comedy that Cusack co-scripted and starred in. This film proved to be a career resurgence for Cusack. He played a world-weary hitman who returns to his ten-year high school reunion and attempts to reconnect with the girl he stood up on prom night, played by Minnie Driver. Interestingly, life mirrored art when Cusack actually attended his own ten-year reunion (to fulfill a bet related to the film’s financing) and subsequently began a real-life romance with Driver. Grosse Pointe Blank is a standout among John Cusack movies, blending action, comedy, and romance in a unique way.
Grosse Pointe Blank (1997) marked a career resurgence for Cusack and is celebrated for its unique blend of genres.
Following Grosse Pointe Blank, Cusack took on a role in the action-packed Con Air (1997), where he played a federal agent. He humorously described his character as “the first post-Heston, non-biblical action star in sandals,” indicating his playful approach even to mainstream roles. Cusack chose Con Air as a strategic career move, recognizing the importance of balancing artistic integrity with commercial considerations. He then collaborated with Clint Eastwood in Midnight in the Garden of Good and Evil (1997), portraying a Yankee reporter investigating a murder case in Savannah, further showcasing his versatility across different genres and directorial styles.
Cusack’s preference for unconventional and original material became even more apparent with his role in Being John Malkovich (1999). Almost unrecognizable with long hair, a beard, and glasses, he delivered a compelling performance as a frustrated puppeteer who discovers a portal into the mind of actor John Malkovich. This deeply original and surreal film earned him a Best Actor nomination at the Independent Spirit Awards, highlighting his commitment to challenging and innovative roles. Being John Malkovich remains one of the most critically acclaimed John Cusack movies, celebrated for its originality and unique premise.
Being John Malkovich (1999) is a critically acclaimed film showcasing Cusack’s willingness to take on unconventional roles.
In 2000, Cusack returned to a more clean-cut image in High Fidelity (2000), another New Crime production. He collaborated again with Steve Pink and D.V. DeVincentis to adapt Nick Hornby’s popular novel, relocating the story to their native Chicago. Cusack starred as the sarcastic record store owner who revisits his “Top 5” breakups to understand his romantic misfortunes. High Fidelity is often cited as one of the best John Cusack movies, perfectly capturing his ability to blend humor, pathos, and genuine emotion.
Throughout his career, John Cusack has been romantically linked to several notable figures, including Driver, Alison Eastwood, Claire Forlani, and Neve Campbell, yet he has maintained a relatively private personal life. He also frequently collaborates with his sister Joan Cusack and often includes other Cusack family members in his films, underscoring the strong familial ties within his professional life. While pleased with his accomplished career and ongoing projects, Cusack has expressed that he is still striving for his ultimate artistic goal: to be part of a truly “great piece of art,” indicating his continued ambition and dedication to meaningful work within the film industry. His filmography, filled with diverse and memorable roles, cements his place as a significant and enduring figure in contemporary cinema.
