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Billy May’s

Swinging Affairs

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Billy May; Center, Glenn Miller; Right, Frank Sinatra; Left.
Legendary Bandleader Talks Coming Up As A Jazz Musician In The Genre’s Golden Age As Well As What It Was Like To Perform With Glenn Miller And Frank Sinatra


By David Fantle and Tom Johnson
Reel to Real Special for Modern Times Magazine

May 4, 2015 — For trumpeter, bandleader and veteran arranger Billy May, it was the happenstance of having an empty study period to fill in high school that led him to the tuba and contemplation of a career in jazz.  In a more cosmic sense, he also had the good fortune to come of age during the brief Renaissance in the late 1930s and early 1940s when Big Bands ruled the roost.

“Coming up in the 1930s in Pittsburgh when the big swing bands were flourishing, everything just worked for me,” May told us while relaxing on the couch of his condominium in Burbank, Calif., in 1996. (May died in 2004 at the age of 87.) “I’ve had a wonderful life when I look back. I mean how many people can say that at the age of 14 or 15 they discovered what they wanted to do for the rest of their life and did it?”

Indeed, at age 79, May exuded contentment. With a face and manner that at times suggested a gray, slightly impish cherub, he was – in a word – becalmed. May brought to mind the whole community of Jazz artists of that period – men who were the epitome of cool and who carried their provenance in their instrument cases. As a breed, they were hip in a way that most movie stars could only envy.

In 1928, May wrote some arrangements on spec for Charlie Barnet who headed a hot, swinging band. A few months later, Barnet invited May to become the band’s arranger at $70 a week – big money in that Great Depression era. Before long, May was also blowing trumpet for Barnet.

“New York was a blast in those days,” May said. “Barnet’s band played on 52nd Street at The Famous Door. It was a cellar in a brownstone tenement building. The ceiling was about 4 ½ feet off the floor and it was made of metal. We had six brasses in the band and when we hit a combined note, the sound would reverberate off the tin ceiling. The sounds we made are probably still ringing! People would be packed in there like sardines, smoking. They loved it.”

May recalled when he and Barnet trudged home late after a club date. “Charlie came from money and had a three-room suite at the Park Central Hotel,” May said. “In fact, I think his mother owned a piece of the hotel. I bunked there and so did another guy named Herb Reese. He was a song plugger and a good friend of Charlie’s. Well, we came in the room that night and Chick Webb’s whole swing band was there, including Ella Fitzgerald, who was just a young kid starting out as a singer with them. The party lasted ‘til dawn.”

Two decades later, May, as arranger and conductor, would collaborate with Ella on the Harold Arlen Songbook Volumes 1&2 – seminal entries in Fitzgerald’s landmark American songbook series of recordings.

After touring with Barnet for a couple of years, May got a call from Glenn Miller offering him a spot playing trumpet for $150 a week.

“I didn’t particularly like the band, but the money was good and playing with Glenn was considered a prestige gig,” May said. “Miller’s band was No. 1 in the country.”

According to May, Miller’s band was tight and regimented in a way that would have been alien in Barnet’s band.

“Band members had to always be exactly on time for rehearsals, and we even had to smoke Chesterfield cigarettes because they sponsored Glenn’s radio show.”

At the height of Miller’s popularity, May appeared with the rest of the band in two movies – Sun Valley Serenade and Orchestra Wives. And that was when May says that Miller became obsessed with seeing action in World War II.

“He once told me, ‘Billy, this war is going to be a big thing and I’m going to come out of it some kind of a hero.’ He didn’t realize that it would be as a posthumous hero.”

After the war, with Big Bands quickly going the way of the dinosaurs, May relocated to Los Angeles and found work writing musical bridges on The Adventures of Ozzie and Harriet radio show. He also arranged for Bing Crosby, the Andrews Sisters and Harry James, among others.

In addition to fronting his own orchestra, May reached his arranging zenith with his work on a series of Capitol and Reprise recordings with Frank Sinatra, one of which, Come Fly with Me, remains Sinatra’s most popular album from his most fruitful era, the mid-‘50s.

“Writers like to harp on all the trouble Frank caused everybody because it apparently sells books,” May said. “But I always got along very well with him. We did the Come Fly with Me album in about four days. Frank was best on the first take or two. If the band got it right, he’d say, ‘Let’s move on.’ The musicians really dug that attitude, too. Frank could always tell if the band was on. He was a good musician.”

David Fantle & Tom Johnson have been entertainment journalists for more than 30 years and co-authored the 2004 book, Reel to Real: 25 Years Of Celebrity Profiles From Vaudeville To Movies To TV. Fantle teaches film and television at Marquette University in Milwaukee and Johnson is a former senior editor for Netflix. They can be reached at
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