Sydney Leff, 104; Artist Illustrated Covers for Sheet Music of Jazz Age

Sydney Leff, who depicted the moon-June-spoon romance of the Jazz Age through sheet music illustrations for hundreds of popular songs, died Dec. 10 at an assisted-living home in Ossining, N.Y. He was 104.

In the 1920s and ‘30s, Leff was among the handful of pacesetters in a field that flourished until radio, film and television replaced family gatherings around the piano.

“He was the best and the last,” said William Zinsser, the author of “Easy to Remember: The Great American Songwriters and Their Songs.”

Leff used angular Art Deco designs to convey the antic or romantic rhythm of songs by Irving Berlin (“A Little Bungalow”), Harold Arlen (“Stormy Weather”) and Duke Ellington (“Sophisticated Lady”).

Acknowledging a formulaic aspect to his work, he said he leaned heavily on images of swaying palm trees under an inviting moon and flirtatious flappers who hinted at erotic possibility.

His illustration of Gus Kahn and Walter Donaldson’s “Yes Sir, That’s My Baby” featured a woman in an alluring tangerine wrap set against a pastoral scene with an all-American town in the distance.

It was an ideal blend of sex and safety that helped sell the song -- 25 cents a copy at Woolworth stores.

Leff once summarized his work by saying, “I knew where to put the moon and the stars ... and made sure the ladies’ gowns were very up-to-date.”

Leff was born Nov. 18, 1901, in Brooklyn, N.Y., the youngest of eight children of Austro-Hungarian immigrant parents.

He had little desire to become a starving artist.

To learn commercial art, he rode the subway every day to a vocational high school in East Harlem.

A classmate was Al Hirschfeld, who became the revered theater caricaturist and illustrator for the New York Times.

In 1923, Leff responded to an advertisement by composer and lyricist Sam Coslow, who was looking for an artist to design sheet music illustrations.

Coslow, who went on to write “My Old Flame,” “Just One More Chance” and “Cocktails for Two,” among other pop standards, paid Leff $15 for his work and encouraged him to continue.

Leff freelanced, making a comfortable living doing at times four covers a day for $25 apiece. Many of the songs were so forgettable (“Rock Me in a Cradle of Kalua”) that he seldom needed to hear the music played to craft an acceptable cover drawing of a crescent moon floating in a raven sky above a peaceful slice of beach.

He made an exception for Berlin, a particular fan of his work who insisted the artist remain on hand to listen to his songs.

“He and I became very close,” Leff once told the New York Times. “He was very concerned that I capture visually what he did on a song.”

In his prime, Leff was a bon vivant known for his elegant style and a fondness for costume parties.

He once said he missed his early work because of the life he led then.

“We would hang out all night at places like the Algonquin, just talking,” he said. “It was fun, creative, a gay, lovely time.”

Leff left the industry when the sheet music publishers began dropping pen-and-ink illustrations in favor of still shots from movie musicals -- for example, Fred Astaire and Ginger Rogers dancing to a Berlin ballad

Later, Leff did freelance design work and was an art director with a Madison Avenue advertising agency.

He is survived by two daughters; four grandchildren; and five great-grandchildren.