Cusack was born on June 28, 1966 in Evanston, Illinois, to an Irish American Catholic family. His father, Dick Cusack (1925–2003), as well as his siblings Ann, Joan, Bill, and Susie have also been actors; his father was also a documentary filmmaker, owned a film production company and was a friend of activist Philip Berrigan.
Cusack's mother, Nancy, is a former mathematics teacher and political activist. Cusack spent a year at New York University before dropping out, saying that he had "too much fire in his belly".
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