Bennett was born in Wilmette, Illinois (a suburb of Chicago), the son of Sarah and Andy Bennett. He performed in multiple shows at Children\'s Theatre of Winnetka. He graduated from New Trier High School in 2003 where he played Jean Valjean in his school\'s production of Les Misérables. Beck attended the USC School of Dramatic Arts in the B.F.A. Acting program.\n', '

In 2003, Bennett joined the improv/sketch group Commedus Interruptus along with Kyle Mooney and Nick Rutherford. In 2007, after graduation, Mooney, Rutherford, and Bennett joined with editor/director Dave McCary to form the sketch group Good Neighbor. The group received praise from comedian Louis C.K. and director Steven Spielberg, who sent Mooney, Bennett, Rutherford, and McCary a personal acknowledgement after being impressed with the Hook parody, Unbelievable Dinner. He complimented the sketch and encouraged the group to continue making funny movies.\n', '

In 2011, Bennett created the satirical political talk show Fresh Perspectives, which helped him land his AT&T commercials interviewing children.\n', '

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