Paolo was born in New York City, the son of Julia Mendelsohn, a vocal coach and classical pianist, and Colin Paolo, a writer and screenwriter. Paolo is Jewish.
He attended, beginning in 2006, the Professional Performing Arts School alongside Sarah Hyland, Paul Iacono and Taylor Momsen. He took acting classes at the Lee Strasberg Theatre and Film Institute. Paolo also attended Appel Farm Arts and Music Center Summer Arts Camp located in Elmer, New Jersey for several summers. He attended New York University for one semester in fall 2008.
He played a preteen murderer-rapist in an episode of Law & Order: Special Victims Unit. He made his motion picture debut in Clint Eastwood's Oscar-nominated Mystic River, playing young Sean. In 2004, Paolo was on One Life to Live as Travis O'Connell, a recurring character. Paolo also made a return appearance on Law & Order: Special Victims Unit, playing a disturbed teenager based on the real case of Justin Berry. Other films include World Trade Center for Oliver Stone in 2006; Snow Angels, directed by David Gordon Green; and Favorite Son, his first leading role.

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