I’ll Never Smile Again, a song penned by a Jewish songwriter from Toronto, launched Frank Sinatra’s career and held the No. 1 spot on Billboard for 12 weeks in 1940.

Since then, I’ll Never Smile Again, written by Ruth Lowe, has been recorded by dozens of artists, including Count Basie, Fats Waller, George Shearing, Billie Holiday, Michael Buble and, most recently, by Toronto singer Molly Johnson.

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The sad story behind the song was a factor in the success of the standard penned by his then 25-year-old mother in 1939, Tom Sandler said. Lowe, a talented pianist, joined an all-girl touring band in 1935. While in Chicago, she went on a blind date with Harold Cohen, a song plugger. They married in 1938, but a year later, Cohen died during routine surgery at the age of 29.

Devastated, Lowe returned to Toronto. One night she sat down to play piano and transformed her mood into the melody for I’ll Never Smile Again, Sandler said. Meanwhile, Lowe’s family was in financial straits. To help support them, Lowe got a job playing piano at CBC, where she met the bandleader Percy Faith, who recorded I’ll Never Smile Again.

When Tommy Dorsey came to town with his band, along with his new vocalist, Sinatra, Lowe pitched the song to Dorsey, who was likely impressed that a young woman had an orchestrated arrangement of her song on record, Sandler said. “He had tried a couple of other songs with Sinatra before they did I’ll Never Smile Again and they didn’t go anywhere, and they were looking for a song that would launch his career. When he heard I’ll Never Smile Again, he knew that it was ‘the’ song.”

Another factor in the song’s success was its timing, he said. “The war had just broken out and women were losing their husbands. It was a song that everyone could relate to.” Sinatra, who would have turned 100 on Dec. 12, liked I’ll Never Smile Again so much that he asked Lowe to write another song for him. She then co-wrote Put Your Dreams Away, which became Sinatra’s signature closing song in the 1940s. It was played after his funeral in 1998.

Once Lowe got over the tragedy of losing her young husband, she had a lot of fun, Sandler said. In 1945, shortly after another blind date, Lowe married the late Nathan Sandler, the first Jewish member of the Toronto Stock Exchange. They had two sons, Tom, who was named after Tommy Dorsey, and Stephen.

“She was crazy about my dad and they had a great relationship,” Tom said. Lowe didn’t stop writing songs, though. One of them, an upbeat gospel tune she wrote with Sandler, called Take Me To The River, was recorded by The Travellers in the 1960s.

Sandler remembers a parade of well-known local musicians, including Rob McConnell, Peter Appleyard and Oscar Peterson, visiting his family’s Forest Hill home. Lowe also kept in touch with some of her songwriter pals, among them, Sammy Cahn and Johnny Marks (the Jewish American songwriter who penned Rudolph, The Red-Nosed Reindeer), and she frequently visited music publishers in the Brill Building in New York.

Sandler said his mother, who died in 1981, was a musician’s musician and has been credited with being one of the architects of the American ballad.

Seven years ago, Sandler, a photographer, was hired to take pictures at a charity event where he met the musical giant Quincy Jones. Jones told Sandler he’d first heard I’ll Never Smile Again when he was 10 years old. “Not only do I only remember the song, I remember the story behind the song. It was one of the songs that inspired my career,”  Jones told Sandler.   

I’ll Never Smile Again has been inducted into the Grammy Hall of Fame and into the Canadian Songwriters Hall of Fame, along with Put Your Dreams Away.