As the eldest member of the Cusack acting dynasty -- the sister of John, Joan, Susie, and Bill Cusack -- Ann Cusack was raised, like her siblings, in the affluent Chicago suburb of Evanston, but achieved fame and success as a comedic actress somewhat later than the others. Born in 1961, Cusack received her formal education at the Piven Theater Workshop (studying basic improvisation with Joyce and Byrne Piven) and later at New York University's Tisch School for the Arts, where she studied dramatic performance under the aegis of the legendary playwright and theatrical and film director David Mamet. Cusack landed her premier feature-film role at the age of 30, as Shirley Baker, a WWII-era baseball player with a more than slight illiteracy problem, in Penny Marshall's summer 1992 comedy A League of Their Own (alongside Tom Hanks, Geena Davis, Madonna, and Rosie O'Donnell). In the process, Cusack imparted to the film some of its biggest and most unanticipated laughs -- no mean feat, given that cast.
The turn did not go unnoticed, and parts rolled in steadily for the remainder of the 1990s and into the 2000s. The characterizations began small, with low billing -- such as that of a waitress in Harold Becker's poorly received 1993 thriller Malice, and that of a TV woman in Mike Nichols' 1996 La Cage aux Folles redo The Birdcage. Not long after, however, Cusack received her highest television billing (up through that time) when cast as Karen Foxworthy, TV wife and second-string to redneck-obsessed comedian Jeff Foxworthy, in the second season (1996-1997) of the short-lived sitcom The Jeff Foxworthy Show. Unfortunately, the show folded in 1997.
The parts continued unabated, however, in films of varying reception. Cusack teamed up with her brothers John and Bill and sister Joan, as well as Dan Aykroyd and Minnie Driver, in the sadly overlooked dark comedy Grosse Pointe Blank (1997, a work that John co-produced and co-scripted). Ann fared worse (as did the entire cast) by signing on for a re-team with director Mike Nichols in that helmer's 2000 turkey What Planet Are You From?, starring Annette Bening and Garry Shandling. Cusack then made intermittent appearances on such series programs as Charmed and Frasier during the late '90s and early 2000s. In 2006, Cusack essayed the supporting role of Deanna in Aaron Wiederspahn's The Sensation of Sight (2006), a moody, evocative drama (and festival cause célèbre) about a dissatisfied middle-class man (David Strathairn) who drops out of his life and takes a job selling encyclopedias.