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Timeless: Live in Concert, recorded at her Las Vegas show on New Year's Eve 1999, takes as its subject the star herself. It opens with a dramatization of her first, amateur recording session, with young Lauren Frost playing a part described in the credits as "Young Girl," though Streisand later refers to her as "mini-me." Frost doesn't get too far before being joined by Streisand herself on a stirring version of "Something's Coming" from West Side Story. The rest of "Act One" traces Streisand's career from her club days to her movie performances. "Act Two" has less of a narrative structure, though it is equally autobiographical, with Streisand displaying and commenting on videos of herself performing with other stars and building up to the stroke of midnight with a combination of old, recent, and new specially written songs. At 57 that night, Streisand remains in good voice.

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In 2009, in celebration of her new album Love Is the Answer, Barbra Streisand announced she would perform one special concert at the Village Vanguard in New York City, New York. Streisand was backed by a quartet consisting of Tamir Hendelman (piano), Jeff Carney (bass), Brian Koonin (guitar) and Ray Marchica (drums). The audience included special guests and celebrity friends of Streisand such as Bill, Hillary and Chelsea Clinton, Sarah Jessica Parker, Barry Diller and Diane von Fürstenberg, Rosie O'Donnell, Sandy Gallin, Frank Rich, Donna Karan, Lea Michele, and Nicole Kidman, as well as 100 competition winners.

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