Benjamin was born on May 23, 1966 to a Jewish family in Worcester, Massachusetts and graduated from Worcester Academy in 1984 and Connecticut College in 1988.\n', '

Benjamin\'s comedy career began at age twenty-four in Boston where he was in a comedy duo with Sam Seder, then a member of Cross Comedy, a comedy team led by David Cross. For the first seven years of his career, Benjamin almost exclusively worked in groups rather than independently. Afterwards, his independent work remained more experimental, rejecting traditional styles of stand-up comedy.\n', '

Benjamin\'s live projects include the Midnight Pajama Jam, a show performed in New York City with Jon Glaser, and Tinkle, a show combining stand-up comedy and live music co-hosted by Todd Barry and David Cross. A Midnight Pajama Jam DVD is currently in production. He and Cross also appear together on the album Invite Them Up.\n', '

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