Billy May was the arranger-conductor who first collaborated with Sinatra on the 1958 album Come Fly with Me.
The album marked Sinatra’s first collaboration with May and was conceived as a musical journey around the world. May arranged and conducted the sessions, giving the record a bright, swinging sound that matched songs about travel, including the title track, “Around the World,” and “April in Paris.”
Sinatra had already developed important partnerships with arrangers such as Nelson Riddle and Gordon Jenkins, which makes this question easy to mix up. Riddle was especially associated with Sinatra’s influential Capitol recordings, while Jenkins worked with him on several major projects. After Come Fly with Me, May also arranged Come Dance with Me! in 1958 and Come Swing with Me! in 1961.