In 1989, he played Lloyd Dobler in Cameron Crowe's Say Anything....
His roles broadened in the late 1980s and early 1990s with more serious-minded fare such as the politically themed True Colors and the film noir thriller The Grifters.
He was in attendance, along with fellow Cubs fans Bill Murray, Eddie Vedder and Bonnie Hunt during the Cubs' historic Game Seven victory during the 2016 World Series.
He has also been spotted at multiple Chicago Bears games and attended many Stanley Cup Finals games in support of the Chicago Blackhawks. If that means sleeping in and walking around the house in my crocs and a bathrobe till three in the afternoon, I welcome that appealing lifestyle - all day." Cusack trained in kickboxing under former world kickboxing champion Benny Urquidez for over 20 years.
Between 20, Cusack wrote blogs for The Huffington Post, which included an interview with Naomi Klein.
He is engaged now to a really beautiful brunett--a Virgo girl that rides motorcycles.She's a bit older than him, actually, and a lawyer, but a dead ringer for Catherine Zeta Jones.JC definitely has a type, and he likes them brunette and SMART.After establishing New Crime Productions, Cusack experienced box office success with his roles in the dark comedy Grosse Pointe Blank and the Jerry Bruckheimer blockbuster Con Air.
In the years since, he has appeared in roles such as an air traffic controller in Pushing Tin, an obsessive puppeteer in Being John Malkovich, a lovesick record store owner in High Fidelity and a Jewish art dealer mentoring a young Adolf Hitler in Max.She was friends with sister Joan Cusack's husband (also a lawyer) who introduced them.