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She majored in American Studies, enrolling in a theater course. She played Jerry's girlfriend, an artist who painted a famous portrait of Kramer.Her first theatrical production was the Wendy Wasserstein play Uncommon Women and Others, during her junior year at Wheaton. Keener then earned her first starring role in Johnny Suede with the then unknown Brad Pitt.He was not seen with a girlfriend immediately after the separation which rules out that option in the reason for the separation.Keener’s relationship with Benicio is very private.She announced that she was dating him and the next year, they broke up.He went on to his next girl after a few months, but, she still remains single. She does not talk about the separation, break up or her son.There were no known romantic affair or long term arguments that ended the 17 year relationship.Dermot also does not talk a lot about the separation, his life with Keener and the relationship with her after the separation.
In 2008, Keener portrayed Philip Seymour Hoffman's wife Adele in Charlie Kaufman's directorial debut, Synecdoche, New York.
Her performance gained critical acclaim and earned her first Independent Spirit Award nomination for Best Female Lead.
She went on to work with director Tom Dicillo, again, in Living in Oblivion (1995).
In 2001, she worked with director Nicole Holofcener in Lovely and Amazing garnering her a third Independent Spirit Award nomination.
In 2002, she co-starred with Edward Norton in the off-Broadway revival of Burn This and the film Death to Smoochy.
Keener starred in the six-episode HBO miniseries Show Me a Hero, based on the 1999 nonfiction book of the same name by Lisa Belkin.