With Other Record Labels
The Crosby-Clooney collaboration was a sequel to their earlier album on RCA Records, Fancy Meeting You Here, also arranged by May.
May’s other non-Capitol work included another Bing Crosby duet album, this time with Louis Armstrong, entitled Bing & Satchmo; a further duet album twinning Bobby Darin with Johnny Mercer, called Two Of A Kind; the sixth in Ella Fitzgerald's acclaimed series of Song Books for Verve Records, Ella Fitzgerald Sings the Harold Arlen Songbook; a similar dip into the Rodgers and Hart opus with Anita O'Day, entitled Anita O'Day and Billy May Swing Rodgers and Hart; Mel Tormé’s Latin-flavoured album ¡Olé Tormé!: Mel Tormé Goes South of the Border with Billy May; early albums by Jack Jones (Shall We Dance?) and Petula Clark (In Hollywood); one solitary session with Sarah Vaughan for Roulette Records in 1960, to record the single The Green Leaves of Summer and three other tracks; and two more albums with Keely Smith, recorded nearly forty years apart – CheroKeely Swings from 1962 and Keely Sings Sinatra, one of May’s last pieces of work, from 2001.
After Sinatra left Capitol to start his own label, Reprise Records, May continued to provide arrangements for him, off and on, for nearly thirty more years, working on the albums Sinatra Swings, Francis A. & Edward K. (with Duke Ellington) and Trilogy 1: The Past, as well as the chart for one of Sinatra's last ever solo recordings, "Cry Me a River" (1988). In addition, May was the natural choice to arrange Sinatra's knockabout duet with Sammy Davis Jr., Me And My Shadow, which was a hit single on both sides of the Atlantic in 1962, whilst he also contributed to Sinatra's ambitious "Reprise Musical Repertory Theatre" project, providing a few arrangements for three of its four albums, South Pacific, Kiss Me, Kate and Guys and Dolls, May's charts being variously performed by Sinatra, Davis, Crosby, Dean Martin, Jo Stafford and Lou Monte and yielding a perennial Sinatra concert favourite, "Luck Be A Lady" from Guys and Dolls.
In 1958, May arranged a holiday album on Warner Bros. Records featuring the Jimmy Joyce Singers, titled A Christmas to Remember.
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