Kelley was born in Waterville, Maine, raised in Belmont, Massachusetts, and attended the Belmont Hill School. His father is Jack Kelley, a member of the United States Ice Hockey Hall of Fame. Kelley was a stick boy for the New England Whalers of the World Hockey Association in their inaugural season of 1972-1973 when his father coached the team. Kelley was captain of the Princeton Tigers men's ice hockey team at Princeton University, where he graduated in 1979 with a bachelor's degree in political science.
Demonstrating early on a creative and quirky bent, in his junior year at Princeton, Kelley submitted a paper for a political science class about John F. Kennedy's plot to kill Fidel Castro, written as a poem. For his senior thesis, he turned the Bill of Rights into a play. "I made each amendment into a character", he said. "The First Amendment is a loudmouth guy who won't shut up. The Second Amendment guy, all he wanted to talk about was his gun collection. Then the 10th Amendment, the one where they say leave the rest for the states to decide, he was a guy with no self-esteem." Also while at Princeton, he was a member of the Princeton Triangle Club.
He received his Juris Doctor (J.D.) from Boston University School of Law, where he wrote for the Legal Follies, a sketch comedy group composed of Boston University law students which still holds annual performances. He began working for a Boston law firm,[which?] mostly dealing with real estate and minor criminal cases.

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