Bobby Darin guy was the quintessential performer.

He had talent, charisma, class and such professionalism. From a disadvantaged background, and diagnosed at a young age with a terrible disease, he knew he was on borrowed time, and that drove him to be what he became – the best.

He had everything going for him … except time.

Bobby Darin was the real deal — an incredible talent who excelled as a songwriter, singer, musician, and performer.

In my opinion, this New York native remains almost criminally overlooked and under-appreciated, even to this day. His timeless style, class, and undeniable talent set him apart. Though I wasn’t around to witness him firsthand, I have a deep love for his music and so much of the iconic sounds from the late ’50s and early ’60s.

Bobby Darin was born as Walden Robert Cassotto in New York in 1936.

His sister was his mother
Growing up in a tough neighborhood in the Bronx, he faced challenges right from the start. (Bobby later claimed that 40 percent of his childhood friends ended up in prison.)

His father was said to have died before he was born, and Bobby’s mother, Nina, relied on welfare to make ends meet. But there was a twist: Nina was just 18 when she had Bobby out of wedlock, so the family pretended that Bobby’s grandmother was his mother, and Nina became his “older sister.”

The truth of this family secret wouldn’t come out until 32 years later, when Nina finally revealed it to her son. Bobby was devastated by the revelation, and the pain only deepened when Nina refused to disclose the identity of his real father, taking that secret to her grave.

Then, in 2020, a shocking discovery was made: through familial DNA testing, Bobby Darin’s biological father was finally identified, and it turned out he hadn’t died before Bobby was born — he passed away much later, in 1965.

Taunted by other kids
Despite the complicated start, Bobby showed promise early on. He graduated from the prestigious Bronx High School of Science, though his time there wasn’t easy. Taunted by other “smarter” students, Bobby developed a toughness and edge that stayed with him throughout his life.

But he was also a fragile and sickly child, making it impossible for him to join in on normal stickball games or roughhousing with other kids his age.

As a teenager, he taught himself to play drums, piano, guitar, and harmonica, showing a natural flair for music. He later enrolled at Hunter College in New York City but soon became disillusioned with academics and the life in the Big Apple.

Instead, he channeled his frustrations into songwriting, and when a young publisher named Donnie Kirschner saw potential in his work, Bobby’s career took off.

Bobby Darin’s rise to fame happened fast, and there are many theories about how he chose his stage name. Some say he picked ”Darin” from a phone book, while others suggest it was inspired by the name of a Chinese restaurant or actor Darren McGavin. But no matter what name he performed under, his legal name — Cassotto, his mother’s name — always remained close to his heart.

”My legal name will remain Cassotto. Cassotto was my mother’s name, and it will be my children’s name,” he said.

In 1958, Bobby had his first big break with the hit single “Splish Splash,” a song he famously wrote in just 12 minutes. The catchy tune sold 100,000 copies in just three weeks, turning Bobby into a teenage idol practically overnight.

A year later, he followed up with the self-penned ballad “Dream Lover,” which quickly became a multi-million seller and solidified his status as a star.

Then came “Mack the Knife,” a recording that would make history. Based on an earlier version by Louis Armstrong, Bobby Darin’s rendition became an instant sensation. It spent nine weeks at the top of the charts, sold two million copies, and earned him the Grammy Award for Record of the Year in 1960. This was more than just a hit; it was a moment that cemented Bobby Darin as a legend.

Friend with Elvis Presley
In the 1950’s and early 60’s. Bobby had everything going for him. And he wasn’t just rubbing shoulders with the best — he was proving that he was one of the best.

After his breakthrough, the star quickly found himself in the company of legends, becoming friends with the likes of Dean Martin and Frank Sinatra. When Bobby boldly declared to Life magazine that he wanted to become a legend by the age of 25, it ignited a friendly rivalry and lighthearted banter between him and Frank Sinatra.

But it wasn’t just Sinatra who recognized Darin’s extraordinary talent. He shared much in common with another giant of the era — Elvis Presley. Both men were teenage idols, beloved by millions, and possessed a natural, undeniable charisma.

Elvis himself was known to attend Bobby’s concerts, often blown away by the young singer’s performances.

Marrying Sandra Dee
Alongside his music career, Bobby Darin made a significant mark in Hollywood. His first major film, Come September (1961), was a romantic comedy aimed at teenagers, co-starring Rock Hudson and Gina Lollobrigida, and featuring the young actress Sandra Dee. Their meeting during the film’s shoot in Rome would change Bobby’s life forever. At that time, Sandra Dee was America’s sweetheart, enchanting audiences with her girl-next-door beauty and charm.

Bobby once confessed that he knew he wanted to marry Sandra the moment he first laid eyes on her. However, Sandra wasn’t as smitten and initially didn’t reciprocate his feelings. Ultimately, it was her mother, Mary Douvon, who convinced her to go on a date with Bobby. Despite her initial reluctance to acknowledge his advances, their romance blossomed, and the couple married on December 1, 1960.

”Bobby loved me. He was a calculating guy, but I don’t think he arrived in Rome with a plan to marry this new little Mary Pickford of Hollywood,” Dee once said and added: ”Aside from the fact that he was rude, brash and always trying to get a reaction, I didn’t like this person. I just thought, this is a conniving SOB.”

In 196q, the couple welcomed a son, Dodd Mitchell Darin, and their relationship became one of Hollywood’s most talked-about romances. However, behind the facade, their marriage faced challenges, ultimately leading to their divorce after seven years together.

Bobby, who had previously dated Connie Francis, went on to marry Andrea Yeager, a legal secretary he met in 1970. Unfortunately, this marriage also fell apart, largely due to Bobby’s ongoing health issues.

Health secrets
What many of Bobby Darin’s fans never knew was that he struggled with health problems from the very beginning of his life.

He had a history of heart issues dating back to his childhood in the Bronx, where he contracted rheumatic fever as a young boy. This illness damaged his heart, leaving Bobby a frail child who quickly realized that his days were numbered. As a young boy, he overheard a doctor telling his family that ”even with the best medical treatment and luck, the boy probably won’t live to see age 20.”

Aware of the ticking clock, he lived his life to the fullest, understanding that time was a precious commodity.

Throughout the 1960s, he battled heart arrhythmias and extreme fatigue, yet none of that was apparent when he was on stage. His voice was incredibly versatile, seamlessly shifting from rock and roll to traditional pop and country, allowing him to sound completely different with each performance.

Artificial valves
Eventually, it became clear that his health was rapidly deteriorating, and surgery was scheduled in 1971 when Bobby was just 34 years old. The procedure involved inserting two artificial valves into his heart, and it took nearly a year for him to recover. But it helped.

”I had expected to kick off by the time I was 30, so I bought a few extra years,”
he said after he was released from the hospital.

In 1973, Darin had a dental appointment but neglected to take his prescribed antibiotics, which led to a severe case of sepsis. This further weakened his body, and by December, he was admitted to Cedars of Lebanon Hospital in Los Angeles.

Tests revealed that one of the artificial valves installed during his previous surgery was no longer functional, necessitating another open-heart operation – this time, with tragic results.

On the evening of December 19, a four-person surgical team worked tirelessly for over six hours to repair Darin’s damaged heart. Sadly, shortly after the surgery concluded in the early hours of December 20, Bobby passed away in the recovery room without regaining consciousness. He was only 37 years old.

Bobby Darin last will
Bobby Darin’s last wish was for his body to be donated to medical science, so his body was immediately taken to UCLA Medical Center after his death.

”He felt that if there could be any purpose served by dying it would be to help save other people’s lives,” said his spokesperson David Gershenson.

Bobby Darin was a naturally gifted talent whose life, though short, left an indelible mark on both music and film.

His legacy continues to inspire future generations, reminding us that while time may be fleeting, the impact of a remarkable talent can last forever. Share this story on Facebook if you also remember Bobby Darin!