His first hit single was “The Diary”—a song inspired by Connie Francis’ diary because Sedaka really wanted “to look into that little book”—that peaked at 14 in the Billboard Top 100 in 1958. In 1960, Sedaka released “Calendar Girl,” his sixth hit in two years, and his popularity was reaching massive heights.
In 1962, he married Leba Strassberg, whom he met while performing at the now-abandoned Esther Manor resort in the Catskills Mountains, NY.
The resort was co-owned by Leba’s mother, Esther, a businesswoman who wasn’t fond of her daughter being courted by a lowly musician.
Despite Esther’s disapproval, the couple stayed together, all the while dealing with another meddling mom, Eleanor Sedaka.
Earlier confessing that she rode rollercoasters when she was pregnant with him, hoping to miscarry, Eleanor was also pushing her son into pursuing a career as a classical pianist, and not as a pop star.
“She soon changed her mind when I got a royalty check for $62,000 for ‘Stupid Cupid.’ My father was a taxi driver and never made more than $10,000 a year,” Sedaka said, adding that he made the mistake of giving the money to his mom, who, along with her lover, later controlled most of his rights as an artist, including his royalties and finances.
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