[2] He attended the Jules E. Mastbaum Area Conservatory and Vocational School where he trained as a percussionist on timpani, vibraphone, xylophone, snare and bass drums.
[2] Shepherd was in the U.S. Army for four years, serving in the entertainment corps, and working there improved his skills as a composer and arranger.
[3]: 13 Shepherd left Doggett's group in 1959 and returned to New York, where he worked in pit orchestras for Broadway shows, and as a music copyist and arranger.
[4] In 1964, Jimmy Crawford accepted a job from Sammy Davis Jr. and arranged for Shepherd to take over his orchestra role on the Broadway musical Here's Love.
Black wanted steady employment while his son was in high school, so he left the trio to take a job as the drummer for the house band at Finocchio's Club.
[3]: 2 From 1973 until 1995, Shepherd was the drummer for the house band, a piano, drum and saxophone trio, at Finocchio's Club, a nightclub with drag queen entertainment in San Francisco.
This was a Musician's Union gig five to six nights a week, meaning a steady paycheck and benefits including paying in to Social Security.
[6] In the early 2000s, Shep moved to Orange County in Southern California, performing locally with Jerry Velasco.
[8] Musicians Shepherd worked with included Patti Page, Lionel Hampton, Lena Horne, The Ward Singers, Earl Bostic, Buck Clayton, Odetta,[9] as well as Cab Calloway, Sy Oliver, Big Maybelle, and Erskine Hawkins.