Born and raised in Miami, the third of five children, Keener got into acting as a student at Massachusetts' Wheaton College, where she starred in a campus production of Wendy Wasserstein's play Uncommon Women and Others. After graduation, she worked as a casting assistant before landing her first major role, at age 26, in 1989's low-budget action-adventure flick Survival Quest, where she met her future husband, actor Dermot Mulroney (The Family Stone). (The couple, who have a 6-year-old son, Clyde, are rumored to be separated.) Four years later she shot a stylized indie called Johnny Suede, playing the put-upon girlfriend of a then-unknown Brad Pitt. The film grossed just $90,000, but marked a turning point for Keener. ''It was the first time I experienced what it felt like to be in a good movie, to be part of something,'' she says. Later, she went on to make three more films with Suede director Tom DiCillo (Living in Oblivion).
In 1992, Keener appeared in a Seinfeld episode as Jerry's dilettante-artist girlfriend, the one who painted that infamous Kramer portrait. It was great fun (''I felt like I hit the f---ing jackpot!'' she says. ''I couldn't believe I was standing on a soundstage with those guys''), but the real creative kinship came when Keener met Holofcener, who cast her as the adorably insecure heroine of her feature debut, 1996's Gen-X dramedy Walking and Talking. ''I was immediately drawn to her vulnerability,'' says Holofcener, who wrote parts in both 2002's Lovely & Amazing and Money specifically for the actress. ''She's beautiful, funny, warm, incredibly intelligent, and all of that comes through in her acting. She knows my style, my rhythm, yet I think my style and rhythm have changed because she's been in my movies. It's a collaboration.'' In Money, Keener plays a woman whose marriage is falling apart and she's more emotionally raw than usual. Referring to a scene in which Keener's character stares sadly at her estranged husband's empty chair, Aniston says, ''It's the simplicity of how she plays it. Keener just has an ability to break your heart.''
A few weeks after lunch in New York, Keener sits cross-legged on the floor of a cozy Santa Monica hotel lounge a few blocks from her house. ''This is really nice,'' she says, gazing out the window at the sun setting over the Pacific. The Oscars were six days ago, and the actress looks relaxed, relieved that her six months of ''stumping'' for various projects are nearly over. She might go see Dave Chappelle's Block Party tonight. Tomorrow, she'll take her son to Disneyland. Other than Wild Things, in which she will play the main character's mom, she has no jobs lined up. And that's okay. Unlike plenty of actresses her age and younger, she's not worried about how she'll look in five years. Or 10. Because as Keener sees it, she hasn't built a career based on her looks, so why should she enter that rat race now? ''I don't have those issues. I'm not trying to preserve anything that never was. That's almost like stopping time. And Jesus,'' she says through another wallop of laughter, ''I don't want to stop time! I want to get another chance in the next moment.''
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