Reubens attended Sarasota High School, where he was named president of the National Thespian Society. He was accepted into Northwestern University's summer program for gifted high-school students, joined the local Asolo Theater and Players of Sarasota Theater, and appeared in several plays. After graduation, he attended Boston University and began auditioning for acting schools. He was turned down by several schools, including Juilliard, and twice by Carnegie-Mellon, before being accepted at the California Institute of the Arts and moving to California, where he worked in restaurant kitchens and as a Fuller Brush salesman.