The Doomed Crooner

1. He Was A Weak Child

Bobby Darin was born Walden Robert Cassotto on May 14, 1936—but his innocence left him far too soon. When he was just eight years old, doctors diagnosed Darin was diagnosed with multiple bouts rheumatic fever, which seriously damaged his heart. The medics painted a grim picture, predicting a short life expectancy for the young boy. It had other consequences, too.

2. His Family Spoiled Him

Because of Darin's precarious health, his family absolutely doted on the boy. They called him "the King" amongst each other, and pampered him within an inch of his life. This was a very bad idea. Before long, Darin grew self-absorbed and selfish.

His own sister admitted, "I’m not saying that he should not have been protected…I’m saying we should have also made him into a human being, and we didn’t do it". But the dye was already in the wool.

3. He Was An Academic Genius Too

With the sense that the grim reaper was always at his door, along with his family's unfailing adoration of him, Darin soon developed a burning ambition to make something of himself. He was a very clever student, outperforming most of his peers...but this had a downside. The other students ruthlessly teased him—and had a shocking effect on him.

4. His Behavior Was Not Charming

During his teen years, Darin developed a somewhat disturbing persona. At that time, he didn’t realize that he was becoming very arrogant, but as time passed, he came to terms with his problem. He said that his bright peers used to tease him and make him feel insecure. That’s why he gravitated towards a career that made him feel better—drama school.

Still, he had one more thing to do before starting out.

5. He Changed His Name

Bobby Darin was well-prepared for drama school and his lifelong dream of being a musician. There was only one minor issue—his name. The way Darin picked his last name was very random. When he saw a malfunctioning sign at a Chinese restaurant saying “Darin Duck” instead of “Mandarin Duck," he felt inspired—I guess.

Some people claim that he picked it out of a telephone book and that the restaurant story was a lie. Indeed, there is no proof for either story. Either way, he was ready to kickstart a career.

6. His Breakthrough Was Amazing

Unfortunately, life didn’t quite go as Darin planned—at least for a while. One recording after the other, he failed and failed. Still, he was resilient and curious—and in 1958, he recorded a song titled “Splish Splash” hoping to have his big break. Finally, he made it—the song sold more than a million copies in the blink of an eye. In fact, it was only the beginning.

7. He Met Someone

From teenagers bopping to the infectious beat to parents smiling at the boyish charm emanating from their radios, Darin's breakthrough had arrived. He wanted to keep pace, so he began collaborating with other newcomers to get inspired and hopefully sell more hits. Life gave him what he wanted, but it also steered him into the company of someone special.

Her name was Connie Francis, a then up-and-coming singer—and she was going to rock Darin's world.

8. He Found His Partner

Francis and Darin were meant to write songs together and try to shine in this dog-eat-dog world. At that time, both of them were famous, but not superstars. Together, though, they had a supernova effect. They started spending every minute together, and as you can guess, their artistic match quickly turned into a romantic flame.

9. He Wooed Her Good

Although it wasn’t love at first sight for Darin, Francis noted that Darin was the love of her life. She didn’t care about anything when it came to Darin. In fact, she once found Darin in bed with two sketchy women, but that scandalous encounter didn't make her bat a single eyelash. Still, their bizarre relationship was about to get even weirder.

One day, after one of Francis’ performances, Darin came up with a wild idea.

10. He Wanted To Elope

Bobby Darin—who had a very prince-like upbringing—was used to getting what he wanted, and he wanted to marry Connie Francis. After her show ended, he said that they should elope and get married. Why? Because he knew there was no way Francis’ controlling father would agree to this.

The only person he needed to convince was Francis, but he forgot one important detail.

11. His Future Father-In-Law Hated Him

Francis’ father despised Darin and he did everything in his power to end this relationship, yet this wasn’t the main problem. The problem was that Francis was a daddy’s girl—and when one day, Francis’ father physically threatened Darin and chased him out of a building, Francis knew that it was either her father or Darin. She called it quits and hurt Darin deeply.

He was sad—but soon realized that he had bigger fish to fry.

12. He Had Extravagant Dreams

Darin wanted to be larger than life. He spent countless hours in the recording studio, obsessing over every note and lyric, striving for a flawless performance. His attention to detail was legendary because he wanted to be legendary. As he put it, “I want to be a legend by the time I'm 25”.

Nevertheless, he knew that he had to expand his horizons if he wanted to be one of the greats.

13. He Had Trouble Memorizing A Song

In 1956, Darin seemed to expand his horizons and made his TV debut. It was a memorable moment for him because it represented the fast-paced environment of TV for him. He scored an appearance on The Dorsey Brothers’ Stage Show and the team expected him to perform “Rock Island Line”.

Darin didn’t know the lyrics and he basically had no time to learn them, so he had to write them on his palms and tried to catch a glimpse of them while performing. This marked the beginning of his multifaceted career—and made him even more arrogant.

14. He Lost A Friend

Darin had a reputation for being a little bit snobby, and it was about to cost him a dear friend. He felt, acted, and lived like a legend, yet some of his old friends didn’t like his attitude. One of them was another legendary musician Sammy Davis Jr who had been friends with Darin for a while.

Fed up with his attitude, Davis told Darin, “Let me know when you stop being a legend so we can be friends again,” and walked out of his life. But not everyone felt as strongly as Davis.

15. He Had A Mentor

Even though some of Darin’s friends shared the same feelings as Davis, others felt very differently. For example, George Burns—who gave Darin his first chance to perform—knew that, beyond his sometimes disturbing bravado, Bobby Darin had a heart of gold. At first, Darin considered Burns as his mentor, but it turned into a more intimate relationship fast.

16. He Had A Father/Son Rapport With Him

Since Darin lost many friends due to his “hard to get along with” personality, he began spending more time with Burns. As time passed by, Burns began thinking of Darin as more of a son. Due to their strong friendship, when Burns' life took a dark and painful turn, Darin was the first one to lend a helping hand.

17. He Took Care Of His Friend

In 1964, Burns lost someone very close to his heart—his wife—and he was significantly depressed. That was when Darin stepped in. Burns said that “When Gracie died, Bobby slept in my bedroom with me for three or four nights”. Not only did Darin take care of Burns, but he also spoke with him and gave him some friendly advice. The advice he gave to Burns changed his life.

18. He Saved Him

Darin noticed that Burns would sometimes cry all night and not sleep at all. The worried musician had to leave at some point, but he wanted Burns to get better before he did. He then suggested Burns sleep in Gracie’s bed so that he’d feel better. This advice changed Burns’ life because he finally started getting some shut-eye, and moreover, learned to move on.

Darin was a miracle worker when it came to solving other people’s issues—even though his own problems were downright alarming.

19. He Began Acting

Multi-talented entertainer Darin was not content with confining himself to a single facet of the entertainment industry. After his TV debut, he then ventured into acting, eager to showcase his talent on the big screen—and he was good at it.

He scored a huge project called Come September—a movie where he shared the lead with the iconic Sandra Dee, an innocent girl-next-door type of actress who became a household name before Darin. Little did he know, he was in for the ride of his life.

20. His Co-Star Was Lovely

When Darin began filming and met his co-star, he was charmed by Dee. According to their son’s recollection, “He was standing on the shore wearing a yellow suit, and she was in a boat just pulling in to dock,” and then he shouted, “Will you marry me?” to which she replied, “Not today”.

According to Darin, it was a mutual attraction, but Dee told a very different story.

21. His Co-Star Didn’t Reciprocate

According to Dee, Darin was nowhere near charming. In fact, she thought he was very arrogant. As Dee put it, "I didn’t want anything to do with him”. She was also very clear with her “I’m not interested” attitude, but Darin was not willing to give up. After all, he'd gotten everything he ever wanted in his life up until this point. So he pressed harder.

22. He Had Finesse, Sort Of

Darin orchestrated numerous gestures and silly jokes to charm his way into Dee’s life. Some of them were very silly, such as chanting “Sandra Dee has a flea," while others were pretty clever. He wooed Dee’s mother and turned her into his wingman, asking her to convince Dee to go on a date with him. It was a good plan, and surprisingly, it worked.

23. He Fell In Love With Her

Darin finally scored a date with Dee—the hard part was over. He planned a carriage ride with her, and their first date was a total game-changer. It was clear that Darin was falling in love with her dangerously fast, but the shocking part was that Dee began to have feelings too.

At the end of the date, Darin’s honesty and sincerity won Dee’s heart.

24. He Got The Girl

In no time, the two became lovebirds, flirting and laughing all over the set. By December 1960, the two wanted to get married. Dee later recalled what happened, saying “I do remember my thoughts that first morning when I woke up in bed with my husband, I thought I had never felt so safe in my life as I felt with Bobby”.

But sadly, this heady honeymoon phase was the only silver lining of their doomed marriage.

25. He Had A Real Son

It was time for Darin to play the role of a real dad in life instead of a pretend one in a story. On December 16, 1961, his beautiful bride gave him an amazing son named Dodd Mitchell Darin. They were a family of three, but sadly, little Dodd just missed the happy family train. He had two very problematic parents.

26. Marriage Wasn’t What He Expected

In the Dee and Darin household, the good times were officially over—yet, Darin didn’t even realize it. He was still living the party life and expecting his wife to join in too. Their son later recalled that Darin expected Dee to be ready and steady for every occasion and every party with “the boys” whether it was at a show or at a casino.

Understandably, this frustrated Dee to no end.

27. His Wife Was Unhappy

Dee began complaining because Darin began treating her as a trophy wife rather than a partner and a friend. She was sick of sitting through shows and then waiting for Darin to come home after he went partying with “the guys”. She recalled, “I had no life, and we had no life together”.

Dee began feeling claustrophobic, so she picked up a filthy habit.

28. They Were Deteriorating

Darin and Dee's messy marriage had stupefying consequences. They were not only harming their lives as a married couple but their professionalism as well. How? Well, they did everything in their power to mess with each other—and once every while, they crossed the line—because in Dee’s words, they were “bored”.

29. They Acted Childish

While Darin emotionally manipulated Dee and often reduced her to tears, Dee eased her pain with a bottle every night. Wanting to retaliate, she would often find silly ways to criticize Darin’s looks.

Dee would demoralize Darin and tell him his toupee was crooked before he appeared on shows to “stir things up”. Darin, once he was done making Dee cry, tapped into his paranoid side and made everything even worse.

30. He Had Conspiracy Theories About His Wife

Darin often obsessed over Dee’s relationships with her coworkers. Since they had fallen in love on set, what was to stop her from having an affair with another one of her co-stars? Therefore, when Dee began the production of her new movie Tammy and the Doctor, Darin began acting overly suspicious every time Dee spent some time with her co-star Peter Fonda.

31. He Wanted Out

In 1963, Darin could no longer shake off the feeling that his wife was having an affair. He acted up and told her he wanted a divorce, telling Dee the nonsensical reason behind this decision. Dee was both furious and disappointed. She repeatedly denied the claims, eventually convincing Darin to rethink his accusations.

Sadly, this didn’t magically solve their problems.

32. He Was Still Jealous

After almost breaking up with his wife, Darin felt like he needed to make an effort, and so did Dee. He committed all his time to being a good father and an easy-going husband, but there was one big issue: his jealousy. He was unreasonable and paranoid.

On one occasion, he lost his mind over the fact that Dee talked to Warren Beatty at a party. He was silent about it—but behind closed doors, it was a different story.

33. He Made A Decision

Darin didn’t know what to do or how to fix his jealousy problem, so he took the easy way out. Still, he wasn’t bold enough to face Dee, so he went behind her back. In a jaw-dropping act, he had his psychiatrist tell Dee that he wanted out. In the blink of an eye, they separated for good...and then began the hardest year of his life: 1968.

34. He Made A New Friend

1968 started off as a very busy year for Darin—he became more politically active and worked on Robert F Kennedy’s presidential campaign. Beyond the working relationship, Kennedy and Darin developed a very close friendship. Darin considered Kennedy his hero, and one of the main reasons he got more involved in politics.

Soon after, Kennedy became the main reason for his grief.

35. He Suffered A Loss

Darin felt strongly about Kennedy—but he almost witnessed his demise. He was traveling with Kennedy and he even made it to the politician's final destination—California. Darin stayed at the Ambassador Hotel and was one of the last people who ever saw him before a horrendous assassination ripped Kennedy out of his life.

36. He Didn't Leave His Side

Darin threw himself into recording new types of music while trying to shake off the trauma of losing Bobby Kennedy. He was so shaken by Kennedy’s death that, reportedly, when the coffin was above ground, awaiting burial, Darin stayed with Kennedy’s body all night.

But this wasn't the only event that turned Darin's life upside down.

37. His Heart Couldn't Take It

Even though he worked tirelessly to live with it, Darin’s heart was very fragile—and he'd had a frail constitution since childhood. As time passed, his heart got weaker and weaker—but his divorce was the last nail in the coffin. By the 1970s, Darin's health was not doing well. He felt alone and miserable, so he went crawling back to Dee.

38. His Ex-Wife Still Loved Him

In the 1970s, his ex-wife saw him getting sicker by the day—and despite their turbulent past, she couldn’t leave him alone like that. According to Dee, “He would come to the door with his vitamins and say, 'I have nowhere to go'". She knew she had a soft spot for Darin, so every time she would let him in and as she put it, “things would start again”.

However, it wasn't long before Darin began knocking on someone else’s door.

39. There Was Another Woman

In 1970, Darin found love for the second time—this time, she went by the name of Andrea Yeager. Unlike Dee, she wasn’t a world-class actress, but a humble secretary. Even Darin’s friends said that “You couldn't have a more stand-up person around you. She didn’t want anything from Bobby,” and Darin fell head over heels in love with her.

40. He Underwent Surgery

After a year filled with medicine and dire side effects, Darin's doctors finally told him that his heart needed surgery. In January 1971, he underwent an artificial valve implant—a painful surgery with a long recovery period. When he opened his eyes, he began the next chapter of his life: trying to heal his broken heart.

41. Love Healed Him

According to one of Darin’s friends, Yeager was “willing to confront the grim reality of his illness and help him in any way she could” and it was working. Darin began performing again, and Yeager was there whenever he felt bad. Reportedly, Darin was often administered oxygen during or after he performed, but he kept performing, and Yeager kept helping him.

Yeager's devotion was undeniable and it influenced Darin to give love another shot.

42. She Became His Wife

After three years of living together, Darin and Yeager decided to turn it up a notch. In the summer of 1973, the two made their wedding vows and became husband and wife—they were already committed to each other in sickness and in health. However, Darin’s sickness tested their limits.

If Darin thought he'd found his "happily ever after," he was so wrong.

43. They Fell Apart

Only four months later, Darin’s worsening health worsened his relationship. He was living in desperation and the woman he once loved had reached the end of her rope. In October 1973, the fairytale romance came to an end and they divorced.

Only 37 years old, Darin was a divorced man for the second time—but fate had another horrible twist in store for him.

44. His Last Visit Was Unexpected

The same year, Darin made a mistake that led to serious consequences. When he had a dental appointment in 1973, he failed to take his antibiotics—which protected his heart. This caused an overwhelming systemic infection and weakened his heart to very dangerous levels. Due to sepsis, he ended up in the hospital.

Sadly, this was the beginning of the end.

45. He Never Woke Up

On December 11, 1973, Darin scheduled another hazardous heart surgery at the Cedars of Lebanon Hospital in Los Angeles. A surgical team worked for six hours straight to repair his heart for the second time. Sadly, this second operation time wasn’t as successful as the one he'd had in 1971. Bobby Darin never woke up. Only 37 years old, the musician passed away in the recovery room.

46. They Made A Movie About Him

Darin’s early death shook some people, while his action-filled life inspired others to share his story. Director Barry Levinson was in the latter group. In 1997, he began working on a film that intended to tell Darin's crazy life story—but like most of Darin’s dreams, it remained unfinished. However, someone else had their eye on the singer's legacy.

Kevin Spacey took over the project along with the help of Darin’s son, Dodd. The result? A biopic called Beyond theSea.

47. His Legacy Was Gone

It seemed like tragedy followed Darin wherever he went, even after his death. In 2008, The New York Times reported that in the Universal Studios fire, Darin’s work—among hundreds of other artists—was destroyed. Based on what we know of him, it was probably best that Darin was not alive to witness this tragedy.

48. They Made A Musical Too

Dodd Darin got involved in a musical project to commemorate his father. The musical—called Dream Lover: The Bobby Darin Musical—aimed to delve deeper into Darin’s problematic relationship with his mother and grandmother. However, Dodd had something heartbreaking to say about the casting of David Campbell in the lead role.

49. His Son Knew He Was The Right Fit

Dodd noted that “You have to have lived something like that to understand it and [Campbell] has, and I think he can relate to my dad, he can relate to the pain”. Campbell must have been a perfect fit to play Darin because the musical received very positive reviews.

After it premiered in 2016, the production got best musical and best male lead nominations. More importantly, it gave Darin and his human side the recognition he deserved.

50. He Learned His Family's Secret

The same year Darin lost Kennedy, he learned something jaw-dropping about his own past. He discovered his family's wildest secret. See, his mother Nina was just 17 years old when she had him, and to cover up her teen pregnancy she passed him off as her younger brother. Instead, Darin grew up believing his grandmother was his mother.

Nina finally confessed this, sending Darin into a tailspin. However, there was another question on the tip of his tongue.