On July 27, 1940, a 24-year-old Frank Sinatra created a first, in a career that would be full of them. “I’ll Never Smile Again,” the 78rpm release by the hugely popular trombonist and bandleader Tommy Dorsey, with lead vocals by Sinatra, became the first No.1 on Billboard’s new Best-Selling Retail Records chart.

A Billboard first

Launched in that week’s issue of the trade magazine, it was the first-ever independent national record survey to be published, polling retailers all over the country. Prior to this, Billboard’s popularity charts had been based on bestselling sheet music, most-played songs in jukeboxes and, in terms of airplay, a small survey of New York radio stations.

“I’ll Never Smile Again” was composed by Canadian songwriter Ruth Lowe in sad circumstances, after her husband died during surgery. The first public performance of the song was by Lowe’s countryman and bandleader Percy Faith, in 1939, before the Dorsey version, featuring Sinatra and the Pied Pipers, became the first to be released, in June 1940.

It entered the chart at the end of that month and claimed that historic top spot on the new Billboard countdown. The song stayed at the summit for no fewer than 12 weeks, before it was replaced by Bing Crosby’s “Only Forever.” The success of “I’ll Never Smile Again” was a key factor in Sinatra’s decision to go solo in 1942; before that year was out, he had started his own classic catalog of hits with “Night and Day” and “All Or Nothing At All.”

Sinatra re-recorded “I’ll Never Smile Again” for the 1965 double LP A Man and his Music, which marked his 50th birthday. He looked back over his career to date with primarily recent, Reprise-era versions of landmark songs, remaking three especially for the release, including this one. He introduced it with the words “1940, and break number two. I was now a singing employee of Tommy Dorsey.”

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