Born in Norwalk, Connecticut and raised in Tucson, Arizona, Pearlman received a degree in English from Columbia University in New York, and began his career in opera as a resident stage director at the Metropolitan Opera from 1964 to 1967 where he worked with Gian Carlo Menotti, Franco Zeffirelli, Luchino Visconti and Tyrone Guthrie.
These experiences led to his first credited direction, the first American staging of Berlioz's Béatrice et Bénédict for the Washington National Opera in the 1964-65 season.
His work there included a version of The Medium recorded by Columbia, the operatic debut of film star Madeline Kahn, and a highly regarded film/live action production of Turn of the Screw with Benita Valente and Eleanor Steber.
His staging of Conrad Susa's chamber opera, "Transformations," produced in Carmel Valley, California in 1977, featured Eastman School of Music students.
In 1995 Pearlman was appointed director of the Lyric Opera Center for American Artists, the Lyric Opera of Chicago's apprenticeship program where he helped launch the careers of scores of young singers, including Nicole Cabell, Erin Wall, Maria Kanyova, Dina Kuznetsova, Matthew Polenzani, David Cangelosi and Christopher Feigum.