Neil Sedaka, a Pop Hitmaker Across Two Eras, Dead at 86

Neil Sedaka, the crooner and songwriter behind memorable hits like “Breaking Up Is Hard to Do,” “Calendar Girl” and “Laughter in the Rain,” died on Friday at age 86.

Sedaka’s reps confirmed his death to Rolling Stone. A cause of death was not revealed.

“Our family is devastated by the sudden passing of our beloved husband, father and grandfather, Neil Sedaka,” the singer’s family said in a statement. “A true rock and roll legend, an inspiration to millions, but most importantly, at least to those of us who were lucky enough to know him, an incredible human being who will be deeply missed.”

Sedaka was one of the most successful performers and writers of the Sixties and Seventies, enjoying two distinct eras of success. In the early Sixties, his sugary pop and doo wop-inflected tunes like “Breaking Up” and “Oh! Carol” dominated the pre-Beatlemania charts. A decade later, he returned as an adult contemporary star with hits like “Laughter in the Rain” and “Bad Blood.”

Sedaka was born and raised in Brooklyn, and his early proficiency at piano earned him a spot at the famed Juilliard School of Music, where he attended both prep school and college. At the same time he was getting a classical education, though, Sedaka was falling in love with early rock & roll and co-founding the doo-wop group, the Tokens. While Sedaka left before the Tokens topped the charts with their famous (if controversial) version of “The Lion Sleeps Tonight,” he’d soon find success of his own. 

Alongside his neighbor and longtime songwriting partner, Howard Greenfield, Sedaka set up shop at the famous Brill Building and helped define the pop style that emerged from the New York City hit factory. Their success with songs like “Stupid Cupid” for Connie Francis helped Sedaka secure a record deal of his own. He notched his first Top 10 hit in 1959 with “Oh! Carol,” then followed it up with notable tunes like “Stairway to Heaven” (not that one), “Calendar Girl,” “Little Devil,” and “Happy Birthday Sweet Sixteen.” The run culminated in 1962 when “Breaking Up Is Hard to Do” went to Number One, and “Next Door to an Angel” peaked at Number Five. 

Not only was Sedaka big in the U.S., he was also a huge star abroad. He bolstered his international appeal by frequently recording his songs in other languages. Over the course of his career, he’d release tracks in Italian, French, Spanish, German, Portuguese, and Japanese. 

The arrival of the Beatles in 1964, however, effectively stunted Sedaka’s solo career. His label eventually dropped him and he found himself in financial straits after learning that his manager (also his mother’s boyfriend) had blown his savings. Sedaka was able to support himself as a songwriter, and his work enjoyed some success, but in an interview with The New York Times last year, he admitted to feeling lost during the second half of the 1960s. 

“I missed it. I missed it with a vengeance,” he said. “I listened to the radio and thought what do I have to do? No more of the tra-la-las and do-be-dos, which I was the king of. I wanted to be an artist that fit into the culture of the time.”

In the early Seventies, Sedaka found refuge and fresh inspiration in England. He gigged at small clubs across the country and met a new set of collaborators, including the members of the burgeoning pop group 10cc. With them, Sedaka recorded two records, 1972’s Solitaire and 1973’s The Tra-La Days Are Over, which further boosted his profile in the U.K. He soon found a staunch advocate in Elton John, who signed Sedaka to his label and helped him mount his comeback. 

In 1974, John’s Rocket Record Company compiled many of Sedaka’s songs from his U.K. era into the compilation, Sedaka’s Back, which earned gold certification in the U.S. The following year would be Sedaka’s biggest: He topped the Billboard Hot 100 twice as a solo artist, first with “Laughter In the Rain” and then with “Bad Blood” (the latter featuring uncredited backing vocals from John), while his new ballad version of “Breaking Up Is Hard to Do” peaked at Number Eight. At the same time, Captain and Tennille went to Number One with “Love Will Keep Us Together” (written by Sedaka and Greenfield for The Tra-La Days Are Over) and the Carpenters hit Number 17 with a rendition of Sedaka’s song “Solitaire.” 

Sedaka cracked the Top 20 two more times as a solo artist, first with the bustling, rock-leaning 1976 tune, “Love in the Shadows,” and then again in 1980 with “Should’ve Never Let You Go,” recorded with his daughter, Dara. Otherwise, Sedaka enjoyed continued success in the adult contemporary space during the late Seventies and early Eighties with hits like “Amarillo,” “Alone at Last,” and “Your Precious Love” (also with Dara). In 1983, Sedaka was inducted into the Songwriters Hall of Fame.

In the coming decades, Sedaka remained busy as both a live performer and recording artist. He dabbled in classical, children’s music, and even recorded a whole album of songs in Yiddish. He released what would be his last studio album, I Do It for Applause, in 2016, and eventually decided to stop writing new music altogether. “I felt if you can’t top it, you should stop it,” he said in a 2020 interview.

Sedaka did enjoy one more revival of sorts, when he started recording and sharing performances from home during the Covid-19 pandemic. The octogenarian proved adept at navigating this new era of short form video. He continued to post after the pandemic, sharing an array of new clips and archival ones on TikTok and Instagram. A video of him playing his first hit, “Stupid Cupid,” this past Valentine’s Day, was viewed more than 338,000 times on TikTok alone. 

“I think the reason I’ve been around so long is I’ve always been able to raise the bar, reinvent Neil Sedaka, and to develop and grow,” he said in that same 2020 interview. “It’s still very gratifying to hear my music played on the radio — the songs will outlive me.”