He has won twelve Grammy Awards and produced the original cast recordings of many of the Sondheim musicals, including Sweeney Todd, Company and Sunday in the Park with George, among others. He also produced the original cast recordings of 1776, La Cage aux Folles and 42nd Street, among over a hundred others. He has produced hundreds of classical music and popular music recordings.
Shepard attended The Juilliard School's preparatory division, training in piano and composition, leaving after his third year, in 1949. He then attended Oberlin College, again studying piano and, privately, composition, receiving his B.A., Music, in 1958. He then continued his studies in 1959 at the Yale Graduate School of Music.
Beginning in 1960, Shepard worked for fourteen years for Columbia Records, eventually becoming co-director of CBS Masterworks. He joined RCA Records in 1974, where he was Division Vice President of RCA Red Seal, responsible for recording, signing and marketing of the label, until 1986. He was then Vice President: Classical and Theatrical until 1989 for MCA Records in New York, where he created their classical and theatrical record line. Shepard then became an independent producer, wrote, narrated and produced The WQXR/MCA Classics Listener's Guide (1988; music appreciation recordings) and has lectured on musical theatre and classical music.
Shepard has produced numerous classical and Broadway cast albums, winning 12 Grammy Awards, including four with songs by Stephen Sondheim. In 1984, he received the NARAS Governors' Award for Lifetime Achievement, and in 1986, he won a Drama Desk Special Award "for preserving musical theater heritage on record." Shepard received two Emmy Award nominations for songs he composed for the PBS television show Between the Lions (2007). He has also produced live concert events, most recently My Fair Lady in 2007, and Camelot in 2008, with the New York Philharmonic, broadcast on PBS as part of the Live from Lincoln Center series. Shepard has arranged music and conducted for Anna Moffo, Richard Kiley, the Norman Luboff Choir and Richard Tucker, among others. He performed as a pianist at various concert venues, and his recording of classical piano pieces and improvisations, "Love on a Stormy Weekend", was released by Planet Earth Recording Co. in 1998.
Shepard is the composer of five musicals and five operas, among other pieces. The operas include That Pig of a Molette (1988) and A Question of Faith (1990), both with libretti by Sheldon Harnick, which were presented as a double-bill under the title Love in Two Countries at St. Peter's Church Theatre, in New York City, by Musical Theater Works in 1991; and a score for the lost music of Thespis (2008), which has been called "a love letter to [Gilbert and Sullivan] and ... might be better than the original". In 1971, he composed the motion picture score for Such Good Friends, directed by Otto Preminger, and in 1974, he wrote a children's cantata, In the Night Kitchen, with words by Maurice Sendak. He also composed the piano folio Folk a la Classique for Carl Fischer Music (2003; original compositions for children) and was the composer and lyricist for children's educational material for the Carnegie Hall Explorers Division, The Children’s Symphony (2004, intended to teach the instruments of the orchestra to second-and third-grade schoolchildren) and for the PBS television show Between the Lions (2007).
Shepard has produced numerous musical theatre, classical and opera albums, including the following. (G) indicates a Grammy Award winner.
Shepard's classical music recordings include albums with Leonard Bernstein, Pierre Boulez and others, and his albums of popular music include, among others:Harold Arlen and Barbra Streisand – Harold Sings Arlen (1966);
Leontyne Price – God Bless America (1982);
Barbara Cook – The Disney Album (1988);
The Boston Pops – Music of the Night (1990);
Betty Buckley – An Evening at Carnegie Hall (1996); and
Julie Andrews – Classic Julie (2001).
In addition, Shepard contributed to the early 1970s "switched-on" cycle of synthesized electronic classical albums, with Everything You Always Wanted to Hear on the Moog* (*but were afraid to ask for), in collaboration with Andrew Kazdin (1973). In the 1990s, he also produced several albums for Sony Classical, with conductor John Williams and The Boston Pops, including The Star Wars Trilogy (Skywalker Orchestra); The Spielberg-Williams Collaboration; I Love a Parade; Kismet, starring Samuel Ramey, Jerry Hadley, Dom DeLuise, Ruth Ann Swenson and Julia Migenes; and The Green Album, among others.