The Jewish Mom Behind Frank Sinatra’s First Big Hit

Frank Sinatra’s first huge hit was the perfectly melancholy “I’ll Never Smile Again.” The song was recorded by a young Sinatra with the Tommy Dorsey Orchestra, and featuring the vocals of a young Sinatra and The Pied Pipers, the song is part of music history — it’s the first song to top the first ever Billboard top 100, published on July 27, 1940, and it stayed at the number one spot of that chart for 12 whole weeks.

The deceptively simple ballad effectively tugs at the heartstrings, with Sinatra crooning about a feeling we all have after heartbreak and loss: we can’t possibly concieve how we will ever love again that same way, how we will ever truly feel joy again. That sense of grief was especially prevalent when the song came out, when so many had to part with their loved ones who were going off to war.

And behind that song? Was one incredibly talented, young Canadian Jewish woman who, in her early 20s, already knew so much grief.

Ruth Lowe was born in Ruth Lowenthal in Toronto, Canada. Her father, Sam, died in 1932, at the height of the great depression, and Lowe worked hard to help provide for her mother, Pearl, and her sister, Mickey, using her gifts as a songwriter and musician. In her 20s, she met Harold Cohen, a Chicago music publicist, and fell in love. The two got married, and Lowe was sure she’d found her ever after, until tragedy struck a year later. Harold passed away of kidney failure during surgery, leaving Ruth a widow at the tender age of 23.

Mired in grief, Ruth turned to her one place of solace: music. At the time, she was touring with Ina Ray Hutton’s all-women big band — one of the first all-female big bands in history — playing piano, but she was also writing songs. She wrote both the heartbreaking lyrics and the tune, for “I’ll Never Smile Again.” Ruth brought the song to jazz man and big band leader Tommy Dorsey, and he gave the tune to Sinatra, as it worked oh-so-perfectly with Ol’ Blue Eyes’ enchanting baritone.

The rest, of course, is music history. “I’ll Never Smile Again” remains one of the most beloved Sinatra songs of all times.

As for Lowe, that song is not the only iconic Sinatra tune that she wrote. Kveller spoke with Tommy Lowe Sandler, Ruth’s son, and got more details about this beautiful musical partnership.

After “I’ll Never Smile Again,” the singer apparently called Lowe — or Ruthie, as he called her — and asked for another song to close out a radio broadcast he was doing. According to Sandler, Sinatra apparently asked his Ruthie to make the song a little more upbeat. Ruth, whose life has been forever changed by “I’ll Never Smile Again’s” commercial success, was happy to do it. But the twist? Sinatra needed it the next day.

“Mom picked herself up off the floor after fainting,” Sandler told Kveller over e-mail. But of course she said yes. “When Sinatra asks you to write him another song, you write him another song!”

At the time, Ruth was collaborating with two music writers in New York, Jewish composers Paul Mann and Stephan Weiss, and they got together for an all nighter, one that produced the song “Put Your Dreams Away.” She called Ol’ Blue Eyes and played it over the phone. After asking whether he liked it, Sandler said, the line went quiet for a bit before she heard him exclaim: “Like it?! I love it!”

The song helped Sinatra close out his shows in the 1940s, and it was also part of his very final act. The Sinatra family played it at his funeral. Ruth Lowe and her lyrics were there for the beginning of his success, and she and her lyrics were there for the end, too.

And in case you’re wondering, Ruth Lowe herself did learn to smile again.

She married her second husband, Nathan Sandler, in 1943. The two raised two boys together, Tommy and Stephen, in a happy Jewish home, full of present-laden, crowded Hanukkah celebrations and delicious Shabbat dinners that included Ruth’s roast beef and potatoes and her signature banana cream pie. She volunteered for her local Hadassah chapter and helped organize their yearly bazaar, often involving her sons. She raised the boys in a house full of music and was especially close to Tommy (named after Tommy Dorsey, of course), who is now a photographer and musician. He shared with us that they’d go to Broadway plays together, stopping to get coffee and cheesecake at Dempsey’s on Broadway. Sandler recalls meeting “Rudolph the Red-Nosed Reindeer” writer Johnny Marks on one such excursion.

Ruth passed way in 1981, at age 68, after a long battle with cancer. A year later, both she and “I’ll Never Smile Again” were inducted into the Grammy Hall of Fame.

In 2020, Tommy and writer Peter Jennings co-wrote a biography of Ruth: “Until I Smile at You: How One Girl’s Heartbreak Electrified Frank Sinatra’s Fame!”