The eldest of five acting siblings, Ann Cusack began her career at the age of nine working with the famed Piven Theater & Workshop in Evanston, IL. The pretty brunette continued to develop her improvisational and other thespian skills at NYU and Circle in the Square. Following graduation, Cusack returned to her native Chicago and worked on the artistic staff at the Goodman Theater before managing The Dance Place in Washington, DC. Returning to the Midwest, she joined an a capella singing group which toured the USA. In 1992, Cusack landed her first screen role in "A League of Their Own" and subsequently played a string of small character roles in such films as "Malice" (1993) and "Multiplicity" (1996). She joined her acting siblings Joan, Bill and John in "Grosse Point Blank" (1997), co-written and co-produced by John Cusack.