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Amy Stiller plays herself as an aspiring actress in Hollywood. Although being born into a famous family, she cannot seem to get a decent acting job. One day she is trying on a bra in a department store and realizes that an image of "The Madonna" has appeared on her left breast.

Amy Stiller's Breast is a comedy short film which came out in 2000, starring Amy Stiller as herself, and featuring her parents Jerry Stiller and Anne Meara as themselves. It was directed by Becky Neiman and written by Henry Joseph, Becky Neiman, and Amy Stiller.

In summer 2000, the New York International Independent Film & Video Festival awarded the film the Grand Jury Prize for Best Short Film.

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