A new book tells the story of Ruth Lowe, the pioneering Canadian songwriter behind two of Sinatra’s earliest hits

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When the Toronto-based songwriter and big-band pianist Ruth Lowe wrote I’ll Never Smile Again in 1939, she certainly believed the sentiment. Less than a year into marriage, she had lost her first husband, a Chicago song pusher named Harold Cohen. In the hospital for a routine kidney operation, he died on the operating table. She composed the lament while still grieving.

The song was the exact opposite of a self-fulfilling prophecy, however. Lowe smiled plenty when it was arranged by Tommy Dorsey for his band’s young singer Frank Sinatra. The recording became a hit, rocketing both Lowe and Sinatra to stardom in 1940. Three years later, she remarried and co-wrote another hit for Sinatra, Put Your Dreams Away (For Another Day).

Lowe is the subject of Until I Smile at You: How One Girl’s Heartbreak Electrified Frank Sinatra’s Fame!, a biography written by Peter Jennings with Tom Sandler, Lowe’s son. Sandler spoke to The Globe and Mail about the song (now considered a standard) and his mother, a pioneering songwriter in a music industry dominated at the time by the fedora-clad gender.

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What kind of person was your mother?

She was fun. She was hip. She was a jazz musician who played in an all-women orchestra and hung out in New York with Frank Sinatra and Duke Ellington. She loved playing cards. She really understood that life was to be enjoyed, and that to find joy and happiness was a highly viable goal in life.

How did her music career begin?

Her father passed away in the mid-1930s. In her late teens, she had to become the sole supporter of her family. She did it by demonstrating music in a Toronto music store. People would come in to purchase sheet music, and they would have a live musician on site play it. That was my mom’s first job. Then Ina Ray Hutton came in with her all-female big band the Melodears to play the CNE Bandshell. Her piano player was sick and couldn’t make the gig. She was looking for a female piano player who could do the jazz stuff. She contacted the Toronto Musicians’ Union and told them if she was blonde, that would be an asset. My mother fit the bill.

The heartbreak of the breakthrough song she wrote, I’ll Never Smile Again, came from a true place, yes?

She had returned to Toronto from Chicago, after her husband died during a routine operation. She wrote it late one night in 1939. She sat down at the piano and in 10 minutes the song was written. The day before she wrote it, she told her sister, Mickey, “I’ll never smile again.” That’s how she was feeling.

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She did smile again, though – ironically because of the song.

It certainly didn’t hurt. When Frank Sinatra recorded it in 1940 with Tommy Dorsey’s band, it was the No. 1 song on the first-ever Billboard chart. All of a sudden, she became a celebrity. There was a lot of attention paid to her artistry and to her ability as a musician. And there was serious revenue coming in. All that is going to cure a lot of problems.

Did she battle sexism?

I don’t think so. She had this magic wand, which was her music. That kind of neutralized everything and everybody.

Your aunt Mickey, your mother’s sister, figures in the story. What was her role?

She travelled with my mom, and was her secretary. She passed away this year, at age 99. She was a wealth of knowledge for this book. She told me once, “You know, your mom brought this guy to the apartment once. He was good-looking, but he didn’t make an impression on me.” It was Frank Sinatra.

Did your mother ever have a romantic relationship with Sinatra?

I don’t think so, to be honest with you. She had just come from this marriage that ended tragically. I don’t know if she was even in a place where she was even thinking about anything like that. She married her second husband, my dad, in 1943. Then she started a family. She had all the things she wanted at that point.

Has she received all the recognition she deserves? Why doesn’t she have a star on the Canadian Walk of Fame?

I’ve been in touch with them. Let’s just say the Walk of Fame people know me very well, and they know her story. I’m lobbying them, and I think I’m close.

Too bad Sinatra’s not around to persuade them. As in, “You’ve got a nice sidewalk there, be a shame if anything happened to it.”

[Laughs] I like that. Let’s see what happens. I’m also hoping to get a Juno named after her. I’ve spoken with them as well. I think it’s time. I think it’s appropriate.

This interview has been edited and condensed.

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