As a child he became very interested in the piano and frequently played organ at the local Bethesda Episcopal Church in Saratoga Springs. He began acting in high school and was recognized as best Dramatic Arts student. He also received the Yaddo Medal for character and scholarship in 1977, and worked in theater while a counselor at Camp Kabeyun, in New Hampshire. However, his love of music was still strong, so he decided to study classical piano at Yale University. Unfortunately, he soon grew bored with music history lessons and found that he wasn’t dedicated enough to practice the required number of hours to become a successful concert pianist. Instead, he graduated in 1981 with a double major in English and Theatre Arts.
At Yale University, Pierce performed and directed student productions, appearing as Sir Joseph Porter, K.C.B., in the Yale Gilbert & Sullivan Society's production of H.M.S. Pinafore; for the same society, he directed the operetta Princess Ida, and occasionally accompanied rehearsals on the piano. Other roles he played as a student at Yale include Vladimir in Waiting for Godot, Cauchon in Saint Joan, and Nick in Who's Afraid of Virginia Woolf?.Pierce then moved to New York City, where he worked several jobs including selling ties at Bloomingdale's and working as a security guard while acting in the theater during the late 1980s and early 1990s and studying at Michael Howard Studios. During this period, he played Laertes in a popular off-Broadway production of Hamlet and made his Broadway debut in Christopher Durang's Beyond Therapy in 1982.