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In the film Addams Family Values, she played serial divorcee and murderer Debbie Jellinsky. One of Cusack's most well-known roles was the head teacher of Horace Green Elementary School, Rosalie 'Roz' Mullins, in School of Rock.
She appeared with her brother John in the movies Sixteen Candles, Grandview, U. A., Class, High Fidelity, Grosse Pointe Blank, Say Anything..., Cradle Will Rock, Martian Child, and most recently, War, Inc.In an instance of life imitating art, Cusack actually did go home for his ten-year reunion (to honor a bet about the film's financing) and ended up in a real-life romance with Driver.Cusack's next appearance was as a federal agent (or, as he described it, "the first post-Heston, non-biblical action star in sandals") in Con Air (1997), a movie he chose because he felt it was time to make smart business decisions.Long-haired, bearded and bespectacled, he was almost unrecognizable in the role of a frustrated puppeteer who stumbles across a portal into the brain of actor John Malkovich.The convincing performance won him a Best Actor nomination at the Independent Spirit Awards. De Vincentis to adapt Nick Hornby's popular novel (relocating the story to their native Chicago), then starred as the sarcastic record store owner who revisits his "Top 5" breakups to find out why he's so unlucky in love.