Shenkman was born to a Jewish family in New York City, the son of Katherine, who was an associate at a law firm, and Shepard A. Sheinkman, who worked for a consulting company. He graduated from Brown University, and obtained a Masters of Fine Arts in 1993 from New York University\'s Graduate Acting Program at the Tisch School of the Arts. Shenkman\'s sister, Elizabeth, is married to British publisher Jamie Byng.\n', '

He began his professional acting career with a small role in the 1994 film Quiz Show directed by Robert Redford and a guest-starring role on Law & Order, his first of seven appearances throughout the run of the show. He also began working in theatre, portraying Louis Ironson in Tony Kushner\'s play Angels in America at San Francisco\'s American Conservatory Theatre. \n', '

While still at New York University, Shenkman played the role of Roy Cohn in a workshop production of the play. He would reprise the role of Louis seven years after playing the role at ACT in the HBO miniseries adaptation, earning Emmy and Golden Globe nominations. Throughout the 1990s, Shenkman combined work in off-Broadway productions in New York with small roles in films such as Eraser (1996), The Siege (1998), π (1998), and Jesus\' Son (1999), Chasing Sleep (2000), and Requiem for a Dream (2000). In 2000, Shenkman gained success in the theatre, co-starring with Mary-Louise Parker in the Manhattan Theatre Club production of Proof, for which he received a 2001 Tony nomination. After the release of HBO\'s Angels in America miniseries, he returned to Manhattan Theatre club in 2004 in Sight Unseen opposite Laura Linney.\n', '

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