Gary Wofsey studied several different musical instruments as well as composition from a very early age. He led various bands through grade school and majored in music composition at Berklee College of Music in Boston, Massachusetts.
In the early 1970s, Wofsey traveled with the Jimmy Dorsey Orchestra. In 1978, he settled in New York and formed a 13-piece jazz orchestra. The jazz orchestra recorded several albums that featured some of the best jazz musicians in New York City. Many of the orchestra's recordings were found in the top ten of countless jazz radio stations throughout the United States and Canada.
In 1982, Wofsey relocated to Japan, where he formed an all-Japanese jazz orchestra that was very popular in Tokyo.
Upon meeting Jill Allen, the couple became co-leaders of a new jazz orchestra based in New York City, and they eventually married.
The Wofseys live in Northwest Florida, where they co-lead a 13-piece jazz orchestra in Pensacola.
Wofsey is best known for his unique ability to play trumpet and flugelhorn simultaneously.