After nearly 61 years of marriage to the love of his life, Neil Sedaka doesn’t have much personal experience when it comes to “Breaking Up is Hard to Do.”
Last year, as he celebrated his 84th birthday, the charming “down doobie do down down” singer—who captivated hearts with his voice—was overflowing with love for his grandchildren, proudly declaring that he was “born married to his wife.”
How could anyone not adore Neil Sedaka? He’s given us so much over the years—his incredible voice and enduring presence in music have been a gift to fans for decades.
A natural talent, Sedaka—who has penned and recorded some of pop music’s most unforgettable tunes—once admitted that, as a child, he was shy about singing in front of others.
“I knew I had an exceptional voice, but I was embarrassed because it was so high,” he recalled. “But when I sang at my bar mitzvah, the rabbi was in tears.”
At just 13, the classically trained pianist—who studied at Juilliard’s Preparatory for Children on Saturdays—teamed up with 16-year-old Howard Greenfield. Together, they began composing songs for Sedaka’s school band, the Linc-Tones, which later evolved into the Tokens.
Working from New York’s iconic Brill Building, the duo crafted a string of hits, including Sedaka’s own “Breaking Up is Hard to Do,” Captain & Tennille’s “Love Will Keep Us Together,” and Connie Francis’ “Stupid Cupid.”
“We had a tiny cubicle with a piano and a bench, but no window,” Sedaka recalled. “You only got a room with a window after you had a hit song.” The pair made just $50 a week, working tirelessly from 9 a.m. to 5 p.m. before pitching their songs to record labels. “It was tough, but it was incredible training,” he said.
Sedaka was the first artist in the Brill Building to record his own songs, and he also became the first to reach the Top 10 with “Oh! Carol” in 1959—a song inspired by his high school sweetheart, Carole King.
His partnership with Greenfield continued until the mid-1970s, and Greenfield, who was openly gay, tragically passed away in 1986 due to complications from AIDS.
At 19, Sedaka left the Tokens before the band skyrocketed to fame in 1961 with hits like “The Lion Sleeps Tonight” and “Tonight I Fell in Love.”
Going solo, his first three releases failed to gain traction, but one song earned him a spot on American Bandstand with Dick Clark, eventually landing him a record deal.
His breakthrough came with “The Diary,” inspired by Connie Francis’ personal diary—Sedaka had always wished he could “peek into that little book.” The song climbed to No. 14 on the Billboard Top 100 in 1958. Two years later, he released “Calendar Girl,” marking his sixth hit in just two years, and his popularity soared.
In 1962, Sedaka married Leba Strassberg, whom he met while performing at the now-abandoned Esther Manor resort in the Catskills.
The resort was co-owned by Leba’s mother, Esther, who wasn’t exactly thrilled about her daughter dating a struggling musician.
Despite her disapproval, the couple stayed together, all while navigating another challenging maternal figure—Sedaka’s own mother, Eleanor.
Eleanor had once admitted to riding rollercoasters while pregnant in hopes of miscarrying. She also wanted her son to become a classical pianist rather than a pop star.
“She changed her mind pretty quickly when I got a royalty check for $62,000 for ‘Stupid Cupid,’” Sedaka said. “My dad was a taxi driver who never made more than $10,000 a year.”
Unfortunately, Sedaka made the mistake of entrusting his earnings to his mother, who, along with her lover, ended up controlling much of his artistic rights, royalties, and finances.
“My father knew about her boyfriend and accepted it, so after the initial shock, I did too,” Sedaka explained. “I even understood it in a way. My parents lived in two rooms with nine other relatives. My dad was thrifty, but the other man showered my mom with jewels, furs, and fancy outings.”
However, they were living lavishly off Sedaka’s money—spending hundreds of thousands of dollars. He found himself unable to pay taxes, left with nothing.
After firing his mother’s boyfriend, Sedaka revealed that Eleanor nearly overdosed on sleeping pills, devastated by the fallout. “She said she didn’t realize it was my money they were spending,” he recalled. “I didn’t speak to her for a year.”
During that time, his devoted wife, Leba, stepped in as his manager.
Just as he was on the brink of financial recovery, The Beatles arrived on the scene, shaking up the music industry—and Sedaka’s fame took a hit.
Although he continued writing for other artists, his dwindling popularity in the U.S. led him to move his family to London, where the music scene was booming.
Reflecting on this period, Sedaka once said, “I used to walk down the street, and people would ask, ‘Didn’t you used to be Neil Sedaka?’ I’d say, ‘I am Neil Sedaka! You haven’t heard the last of me.’”
Determined to adapt, he reinvented his style in the early 1970s, and that’s when he crossed paths with a rising star named Elton John.
At a London party, Sedaka met the “I’m Still Standing” singer, who invited him to sign with his label, Rocket Record Company.
And just like that, Sedaka’s career was reignited. His 1974 album, Sedaka’s Back—the first of three albums under Elton John’s label—marked his grand return to the charts.
In 1983, he was inducted into the Songwriters Hall of Fame, later earning a star on the Hollywood Walk of Fame.
In 2003, he appeared as a guest judge on American Idol, where season two runner-up Clay Aiken later recorded “Solitaire,” a song Sedaka wrote in 1972. Aiken’s version became the best-selling single of 2004.
During the COVID-19 pandemic, Sedaka began sharing mini-concerts on social media, keeping fans entertained. And last September, to celebrate 60 years of marriage, he posted a special concert with three original songs dedicated to Leba. His heartfelt tribute read:
“I’d like to dedicate today’s mini-concert to my beautiful wife, Leba. In September, we will be celebrating our 60th anniversary. Here are three songs especially written for Leba!”
In early May, Sedaka joined Cameo, offering personalized video messages for birthdays, anniversaries, and other special occasions. He announced the news in a short video, wrapping it up with a few lines from “Breaking Up is Hard to Do.”
Fans flooded the comments with love. One wrote, “Been listening to your songs since I was a teenager. I’m now 75 and still love your music! Please don’t stop!!”
Another shared, “Dear Neil, your songs brighten my day. I often find myself humming the melodies you created—they feel like they’ve become a part of me. Thank you for the joy you bring to the world!”
While his music continues to touch lives, Sedaka’s greatest joy is his family.
“I was born married,” he once said. “If you’re lucky enough to have a partner who truly completes you, that’s the greatest gift.”
A devoted grandfather of three—including a set of twins—he and Leba have built a beautiful life together. Their children, Dara (born 1963), an actress and singer, and Marc (born 1967), a writer and editor for TV and film, have continued the family’s creative legacy.
Looking back on his career, Sedaka reflected, “I could have been bigger, but I wasn’t controversial enough. I didn’t do drugs or trash hotel rooms. There was no drama in my private life. I had talent, and I was hungry for fame. And you can’t say I didn’t get it.”
It’s inspiring to see that Neil Sedaka and Leba have remained by each other’s side for so many years, never letting fame come between them.
He is, without a doubt, a legendary artist whose music will continue to inspire generations.
What’s your favorite song that he performed or composed?