- Sister Joan Cusack appeared in 10 of his movies:Class (1983), Sixteen Candles (1984), Grandview, U.S.A. (1984), Broadcast News (1987), Say Anything (1989), Grosse Pointe Blank (1997), Cradle Will Rock (1999), High Fidelity (2000), Martian Child (2007) and War, Inc. (2008).
- During the famous "boom box serenade" scene in Say Anything (1989), he is actually playing his favorite Fishbone tape on the boom box, while Peter Gabriel's song "In Your Eyes" is played in the movie (source: Cameron Crowe commentary on the DVD).
- Some kind of reference to his favorite bands (usually The Clash, The Ramones or The Specials) makes at least one appearance in most of his films. Most of the time, he wears a T-shirt of one of the bands (Say Anything (1989), High Fidelity (2000), Must Love Dogs (2005), etc), but sometimes (Grosse Pointe Blank (1997)) he works in a poster of one of the bands. These bands are typically in the soundtracks to his New Criminal's productions, as well.
- Was originally the actor chosen to play John Bender in The Breakfast Club (1985). At the last minute, things changed and the role went to Judd Nelson.
- Big fan of punk rock music, his favorite band being the Clash.
- In 1994, he attended his 10th year high school reunion in Illinois. He and the producers of the film had made a bet that if they came up with financing for Grosse Pointe Blank (1997), they would all attend their high school reunions.
- He was awarded a Star on the Hollywood Walk of Fame at 6644 Hollywood Boulevard in Hollywood, California on April 24, 2012.
- Is the subject of the song "Honorable Mention" by the rock band Fall Out Boy.
- Close friends with actor Jeremy Piven. They have done 10 movies together: One Crazy Summer (1986), Elvis Stories (1989), Say Anything (1989), The Player (1992), Floundering (1994), The Grifters (1990), Grosse Pointe Blank (1997), Serendipity (2001) and Runaway Jury (2003).
- Growing up John and his siblings often put on plays at their home. He has mentioned that his older sister Ann once staged a production of "Cinderella" in their living room in which she played Cinderella, sister Joan played the Ugly Stepsister, brother Bill played Prince Charming and John played the dog.
- He became interested and started training in kickboxing for his role in Say Anything (1989) as his character Lloyd was a fan of the sport. He trained under kickboxing champion Benny Urquidiez and kept training with him for years afterwards as a hobby, eventually gaining a level six black belt Ukidokan kickboxing.
- Has a production company called New Crime Productions (that produced Grosse Pointe Blank (1997), Fear and Loathing in Las Vegas (1998), and The Jack Bull (1999) among various stage productions) which he founded with two of his high school buddies Steve Pink & D.V. DeVincentis.
- Considers the scripts to Max (2002) and Being John Malkovich (1999) the best he has read.
- On free time, he likes to go "Helicopter Snowboarding" and kickboxing with stunt coordinator Benny Urquidez. Has a black belt in Ukidokan.
- Beat out Christian Slater for the role of Lloyd Dobler in Say Anything (1989).
- Attended a theatre school in Chicago with sisters Joan Cusack and Ann Cusack. The theatre school was managed by the parents of his best friend, Jeremy Piven.
- In 2006, when Total Film magazine asked him for a "Top 5" list of his movies, he answered with The Grifters (1990), Grosse Pointe Blank (1997), The Thin Red Line (1998), High Fidelity (2000) and Max (2002).
- Was once roommates with Jeremy Piven.
- His performance as Lloyd Dobler in Say Anything (1989) is ranked #72 on Premiere magazine's 100 Greatest Movie Characters of All Time.
- Was good friends with Hunter S. Thompson and nearly got to play him in Fear and Loathing in Las Vegas (1998).
- He and his good friend Tim Robbins made six movies together: Bob Roberts (1992), Cradle Will Rock (1999), High Fidelity (2000), The Player (1992), The Sure Thing (1985) and Tapeheads (1988).
- Brother of Joan Cusack, Ann Cusack, Susie Cusack and Bill Cusack. Son of Dick Cusack (actor, documentary filmmaker) and Nancy Cusack (teacher).
- Education: Piven Theatre Workshop (Evanston, Illinois), managed by the parents of actor Jeremy Piven. One semester at New York University.
- Lobbied hard for the role of Thomas "Neo" Anderson in The Matrix (1999) but the role was given to Keanu Reeves.
- Is the product of a passionately liberal Irish Catholic family, visited the radical Berrigan brothers when he was growing up, and, like them, his mother still gets arrested for her anti-militarism and pro-human rights protests.
- Was considered for the role of Billy Flynn in Chicago (2002). However, he ended up losing the role to Richard Gere.
- Was named "Stoner of the Year" by High Times magazine in 2010 (for his performance in Hot Tub Time Machine (2010)).
- Turned down the role of Fred Haise in Apollo 13 (1995), which went to Bill Paxton.
- Turned down the role of David Murphy in Indecent Proposal (1993), which went to Woody Harrelson.
- Is Irish-American. The name Cusack is not Slavic as many may believe. It is a Norman name, brought to Ireland when the Normans invaded in 1169. "Cussac" is a city in South Central France.
- Has worked six times with fellow actor/stuntman/fight coordinator Benny Urquidez in Grosse Pointe Blank (1997), Con Air (1997), The Contract (2006), 1408 (2007), War, Inc. (2008) and Dragon Blade (2015).
- He was rumored to be considered for the role of Walter White on Breaking Bad (2008), which went to Bryan Cranston. Cusack has denied this in later interviews, saying he was never offered the role in any capacity.
- The novel, "Love in the Time of Cholera", by author Gabriel García Márquez, is prominently referenced in two John Cusack movies (High Fidelity (2000) and Serendipity (2001)).
- Has had 24 famous girlfriends: Uma Thurman; Lili Taylor; Claire Forlani; Alison Eastwood; Meg Ryan; Neve Campbell; Minnie Driver; Jennifer Love Hewitt; Jodi Lyn O'Keefe; Corina Katt Ayala; Janice Dickinson; Brooke Burns; Gina Gershon; Shoshanna Gruss; Jami Gertz; Huma Abedin; Rebecca Romijn; Gabriela Spanic; Pamela Anderson; Melissa Gilbert; Sheryl Crow; Susannah Melvoin; Britney Spears; and Alexandra Kerry (*not* all at the same time).
- Tested for the role of Madmartigan in Willow (1988) but lost to Val Kilmer.
- Apocalypse Now (1979) is one of his favorite films.
- Has appeared in two movies as a limo driver, Identity (2003) and 2012 (2009), both with co-star Amanda Peet.
- Attended and graduated from Evanston Township High School, Evanston, Illinois (1980).
- He was awarded the 1990 Joseph Jefferson Award Citation for Director of a Play for "Methusalem" at the New Crime Productions Theatre in Chicago, Illinois.
- Has homes in Malibu, California, and Chicago, Illinois.
- Has worked twice with Nicolas Cage in the films Con Air (1997) and The Frozen Ground (2013). In the first film, Cusack played a law enforcement officer and Cage played a criminal; in the latter film, the roles were reversed.
- Was originally set to play Walter Eberhart in The Stepford Wives (2004). Due to conflicts, he had to drop out and the role went to Matthew Broderick.
- For a long time, he was attached to play the role of Nite Owl in the doomed movie adaptation of Alan Moore's comic-book miniseries, Watchmen (2009).
- Choosen by Empire Magazine as one of the 100 Sexiest Movie Stars in the World (#70) (2007).
- Last name is pronounced Q-zack.
- Was considered for the role of Paul Brenner in The General's Daughter (1999), but was deemed too young at the time, so the role went to John Travolta instead.
- Ranked #15 on Tropopkin magazine's Top 25 Most Intriguing People [Issue #100].
- Good friends with professional volleyball player, Gabrielle Reece.
- Born on the same date as Mary Stuart Masterson.
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