10 Things You Didn't Know About Bobby Darin

"It isn't true that you live only once. You only die once. You live lots of times, if you know how." - Bobby Darin

Yesterday was the 40th anniversary of Bobby Darin's death—and considering he's one of my favorite entertainers of all time, I couldn't let another day slip by without spreading some love for this legend. 

Notice that I chose the word "entertainer" to describe him in lieu of singer or musician. That's because Bobby Darin, as his diehard fans already know, possessed talent that was way more multi-faceted than just being a crooner. 

So many of today's celebs are nothing but phonies with overinflated opinions of themselves; Darin was the real deal. He wrote catchy songs that spanned several genres and composed instrumental music, had mastered several instruments by the time he was a teen, was intelligent, involved in social and political causes, and even scored an Oscar nomination. 

If you think that the only thing Bobby Darin contributed to the world was "Mack the Knife", think again. The man was so amazing that when his son, Dodd Darin, interviewed friends of his father for his biography about his parents, "Dream Lovers: The Magnificent Shattered Dreams of Bobby Darin and Sandra Dee," he said they often burst into tears while waxing nostalgia about his dad; so beloved that he was. 

Here are ten things most non-Darin fans probably don't know about him...

1. He Wasn't Expected to Live Past His 16th Birthday

Born in 1936, Walden Robert Cassotto (Darin's real name) was said by his family to be undersized and frail as an infant, and prone to sickness and accidents. Growing up in the Bronx during the WWII era—before many vaccinations and antibiotics were discovered—Bobby Darin contracted rheumatic fever, an inflammatory disease that can develop a few weeks after a person is infected with strep throat or scarlet fever. In Darin's case, he battled the disease four times between the age of 8 and 13. 

The persistent illness affected his joints so badly he was in constant pain during that time, and attacked his heart valves, plaguing him with health problems for the rest of his life; later in his career, he would have to fortify himself with oxygen backstage in between songs during performances. 

Rheumatic fever led to the first defining moment in Darin's young life when he overheard the doctor treating him tell his family that, even with the best of care, "the boy will not live to see his 16th birthday."

Bobby decided that he was going to prove the doctor wrong, that he would become a showbiz legend by the time he was 25, and that he was going to shoehorn as much into life as he could. 

This included trying to learn pretty much anything and everything he was interested in, from harness racing to tennis (which he admitted was the only sport, try as he might, he just couldn't get the hang of.) 

Unlike so many of us, Darin didn't procrastinate; he couldn't afford to. And when he set his mind to accomplish something, he didn't let anything stand in his way. Unfortunately, this imminent death bomb hanging over his head also made him brash, controlling and arrogant at times, but Bobby expected nothing less than perfection when it came to delivering performances for his fans. 

2. The Woman He Thought Was His Sister Was Really His Mother

Nina Cassotto, Darin's mother, was 16 years old when she found out she was pregnant. She never revealed who the father was, not even to her own family. Perhaps due to the social stigma at the time, it was decided that Darin's grandmother, Polly, would raise him as her own son and Nina would masquerade as his sister. 

When Did Bobby Darin Find Out His Sister Was His Mother?

Darin didn't learn the truth about his mother until he was 32 years old and already a star. He may never had found out if it weren't for the fact that he was getting involved with Robert Kennedy's presidential campaign and hinting that politics was something he was thinking of getting involved with himself. 

The revelation, combined with the death later that year of Kennedy, was a real kick to the groin, especially after growing up never knowing who his father was. It prompted Darin to rethink his life and fame. He decided to free himself of his excess possessions, giving away most of them (including a suitcase phone, the world's first "mobile" phone) to his friends and hightailing to the Big Sur area of California with an Airstream trailer in tow. For several months, he lived in his trailer and began writing folk songs in what became his most creative and prolific period.  

Grandma Polly had experience with music and vaudeville herself, but one has to wonder what kind of background Darin's father came from. Did he ever saw his son perform and know that it was his child? One of those mysteries from music history that unfortunately, will never be solved.  

3. He Recorded Pretty Much Every Genre of Music

Bobby Darin wasn't afraid to take chances with music. While he started his career successfully as a rock and roll teen idol, he knew that bubblegum pop would only take him so far. 

One night he went to see the play The Threepenny Opera, and decided that he was going to record a swing arrangement of the production's signature song, "Mack the Knife", a German ditty about a murderous thug in the cast of characters, Macheath. 

Dick Clark thought he was nuts. He advised Bobby not to record since he risked alienating his teenage audience. Luckily, Darin didn't take his advice. 

The song was recorded in December 1958 and Ahmet Ertegun of Atlantic Records recalled telling Darin that he nailed it on the first take. It was released as a single in August 1959.  By October 5th, 1959, the song rose to No.1 on the national Billboard chart and remained in that position for 9 weeks, earning him a Record-of-the-Year Grammy award for 1959. 

But Darin didn't stop there. He dabbled in country-western, folk, blues, and even gospel. Darin's personality and passion is evident in just about anything he sang. I've heard one male fan say that Darin is the only singer who could make him like the song "Mame." His adaptable vocals were as phenomenal on showstopper Broadway numbers as they were on covers of gentle John Sebastian compositions.

On the catchy "Me and Mr. Hohner", a song he wrote about police brutality against hippies, he even does an early style of rap: 

By the time this song was released, Darin was going by Bob Darin on stage and television appearances because he said it made his name sound more like Bob Dylan. Darin's manager, Steve Blauner, described the music Darin was churning out during this period of his career as "absolutely brilliant." 

Audiences, however, didn't take kindly to Darin's newfound persona during this time; it didn't help that he was sporting a mustache, dressing in denim and refusing to perform "Mack the Knife." After too many boos and walks outs, Darin met them in the middle and went back to wearing a tux and incorporating his classic hits into his set lists. 

And speaking of Bob Dylan, Darin was not only a fan of his, but of The Beatles, The Rolling Stones, and pretty much anyone else on the rock and roll scene during the 1960s. He saw The Beatles and The Stones in concert (and had to put up with Mick Jagger making fun of his sharkskin suit after a performance.) 

I have no doubt that had he lived, Bobby Darin would have embraced and covered the New Wave music of the 1980s. 

Two of my favorite songs written by Darin during the mid and late 1960s are "Change" and "Distractions", the latter being performed on The Tom Jones Show

4. He Really Wanted to Be An Actor

Darin once confessed that given the option of singing or acting, he would have loved to have been an actor. As it is, he was given decent roles in many films over the length of his career, starting with Come September, where he met his first wife, Sandra Dee, and ending with a 1973 Ron Howard film, Happy Mother's Day, Love George

He fared better than Elvis did with his film career, managing to land roles that didn't pigeon hole him into playing a version of himself. He played a Nazi sympathizer opposite Sidney Poitier in 1962's Pressure Point. But it was his portrayal of a soldier dealing with flashbacks after the war in 1963's Captain Newman, M.D. that earned him a Best Supporting Actor Oscar nomination. Darin also made several appearances in television series and specials throughout his career. 

And did you know that he was a master imitator of other celebrities? Here's one of the comedic routines that Darin would perform in concert where he impersonates Marlon Brando, Cary Grant, W.C. Fields and others:


5. He Loved the Ladies--and They Loved Him

Most female fans (including myself) would agree that Darin oozed enormous sex appeal, despite the fact that offstage he was a bit insecure about his height and hair loss, to the point he caved in and began wearing a small hairpiece early is his career.) Marcie Blane's 1962 novelty hit "Bobby's Girl" could have been written about Darin. 

In "Dream Lovers" his son wrote that his dad would often disappear and go off on benders for days at a time—not to drink and take drugs, but to enjoy sexual escapades with women. 

Darin's Uncle Charlie, who raised him as a dad, supposedly played pimp one day while Darin was in his teens to introduce him to the female body and like most red blooded young heterosexual men, from that day forth Darin couldn't get enough. 

He pursued actress and America's sweetheart Sandra Dee relentlessly on the set of Come September until he won her over, and even flirted with Dee's overbearing stage mother Mary to get closer to Sandy. Mama was none too pleased when she discovered Darin's true affections. Darin and Dee were married for seven years, from 1960 to 1967—but according to Dodd Darin's book, the couple continued to rendezvous and share a roof from time to time. Dee never dated another man after Darin passed away in 1973. In 1973, Darin married for the second time to Andrea Yeager, a secretary from his record company. 

At one time or another, Darin was linked with JoAnn Campbell, Bonnie Carroll, Keely Smith, Geraldine Chaplin, Judi Meredith, Judy Harriet, June Blair, Jayne Mansfield, Linda Cristal and Diane Hartford. But there was one lady who really regretted not marrying him, and that was Connie Francis. The reason why a wedding union between the two stars never happened is number six on this list...

6. He Was Almost Killed By Connie Francis' Father

Darin was hired as a songwriter for Francis early in their careers. After a few weeks, Darin and Francis fell for each other. 

For reasons that have never been fully explained, Francis' strict Italian father strongly disapproved of Darin. Maybe it was because of the rumors that Darin's grandfather had mafia ties and died in Sing-Sing prison. Or perhaps he knew that her career would be compromised if she married the Mack the Knife singer. 

Whatever the reason, when Connie's father caught wind of the elopement plan Darin had orchestrated, he waited backstage with a gun when the two appeared on The Jackie Gleason Show, chased him out of the building at gunpoint, and told him to never see his daughter again.

Francis actually did see Darin twice more—once when the two were scheduled to sing together for a television show, and again when Francis was a guest on This Is Your Life. By the time of the show's taping, Darin was married to Sandra Dee.

In her 2017 autobiography Among My Souvenirs, Francis said that none of her four husbands could hold a candle to Bobby Darin. 


7. He Was Involved in Political and Social Causes

Darin was always thinking of his fellow man and became active in many social causes. It started early in his career when he got his dream gig of performing at the Copacabana nightclub.

When he got the gig shortly after hitting it big with "Mack the Knife," the club's owner refused to hire the African American comedian that Darin wanted for the opening act. Darin retaliated by threatening a sit-in outside the club in protest; the club owner gave it. 

He was also present at the 1963 civil rights march on Washington. Later, Darin would get involved in Robert Kennedy's presidential campaign and was at the Ambassador Hotel when Kennedy was assassinated. 

Darin also wrote and recorded an anti-Vietnam song, "We Didn't Ask To Be Brought Here" (carefully disguised as a love song, as was the norm back then.) But one of his masterpieces is "Simple Song of Freedom," a peace aria I'd put in the same category as John Lennon's "Imagine." Singer Tim Hardin had a minor hit with it, and it became a staple at many of Darin's concerts. 

8. He Was a Member of Mensa

Jay Tell, a friend of Bobby Darin, reported on the 30th anniversary of his passing that Darin was a member of Mensa with an IQ of 137, which is only found in the top 2% of the population.

He graduated from the prestigious Bronx High School of Science, a difficult school to get into even if you're considered gifted. He was a huge chess fan, toting a magnetic set with him on movie sets and often explaining chess moves in detail on his variety TV show in between song numbers and comedy sketches. 

It's been also said that Darin had a memory to rival an elephant's; he could meet a fan once and years later still recall their name and face. 

9. He Had His Own Variety TV Show

Like so many other singers of 1970s, Darin hosted his own variety show, The Bobby Darin Amusement Company, which premiered on NBC in July of 1972. The show was a replacement for The Dean Martin Show, and its guest stars included George Burns, Donald O'Connor, Joan Rivers, Dusty Springfield, and Burt Reynolds. Some of the characters that Darin appeared as included Groucho Marx, Dusty John Dustin, a long-haired poet/hippie, and "the Godmother," a spoof on The Godfather which had been released that same year. 

The show returned for a second season on January 19, 1973 (the same day I celebrated my first birthday) under the new name The Bobby Darin Show, updated with an emphasis on Darin performing his classic hits and the latest chart toppers and less comedy routines.

Alas, I've seen some clips of The Bobby Darin Amusement Company which really weren't all that amusing, so this was a wise choice. Darin commented that his friend Flip Wilson constantly reminded him that he was not a comedian, to which he would remind Flip that he was not a singer. 

10. He Donated His Body to Medical Science

1973 was the year that Darin's health began to fail rapidly. It's been speculated that a lack of  sufficient oxygen to his brain resulted in memory lapses. As a heart patient, Darin had to take antibiotics before visiting the dentist as a precaution, but (perhaps due to his failing memory) he failed to take them before a dental procedure in 1973. 

That catastrophic mistake led to a blood infection and additional damage to one of his heart valves. He entered the hospital in December 1973 and a team of surgeons tried to repair the damage, but he died in the recovery room, alone, on the morning of December 20, 1973, without regaining consciousness. The ticking clock that Darin raced against his entire life had finally caught up with him. 

Darin's will decreed that his body was to be donated to medical science; it went to the UCLA Medical Center shortly after his death. It's grim to think of young medical students dissecting Darin's body; there was no funeral, and no memorial or gravesite exists for him. Perhaps he didn't want his loved ones to think of him as truly dead. 

Kevin Spacey, who portrayed Darin in his self-produced biopic Beyond the Sea, once said in an interview that Bobby Darin "had a bad heart, but he was all heart." I know that he's still in the hearts of his fans and if love was all that was needed to save somebody's life, he'd still be with us today. 

Here's some clips of Bobby performing his best-known songs:


  1. I was a big Bobby fan. I knew #1 - #9. Didn't know #10!

  2. Love,love, love Bobby D. I knew most of these 10 but not some of the details. I am so grateful for you tube because I can see recordings of his amazing performances. I really wish he was more appreciated. He is my favorite entertainer of all time too!!!! Thank you.

  3. What a tremendous article this is, Pam! I loved Bobby, too, and appreciate this tribute. I had to look it up to believe he's been gone 40 years. It doesn't seem possible.

    I also had rheumatic fever as a child and can testify about the extreme joint pain one experiences. I cried myself to sleep many nights. Bobby was always aware of the clock ticking. As a result he became an overachiever and, as you pointed out, developed a reputation for being controlling and temperamental.

    I admired Bobby's versatility as a singer, songwriter, musician and actor. His rock 'n' roll records are classics and "Mack the Knife" and "Beyond The Sea" are two of the finest big band recordings ever made. As you noted, he also mastered other styles of music and commanded the respect of Dylan, the Beatles, the Stones and other rock icons.

    To sum it up, Bobby Darin was the real deal. He didn't have to twerk or swing naked on a wrecking ball to attract attention and sell records. The word "star" was invented for people like Bobby. One by one the genuine stars of our time are passing away, leaving a void that today's flavor of the month divas and pop idols will never fill.

    Thank you, Pam, for this fine essay about Bobby Darin.

  4. Those impressions were spot on!

  5. Thanks for the comments, everyone! So nice to hear from other Darin fans.

    And Shady, I was particularly touched to know that you suffered through rheumatic fever as a child, too. I'm so sorry that you had to deal with that. And it's so true that Bobby and so many other entertainers from his time didn't have to resort to ridiculous publicity stunts to get attention. They didn't have to, since their talent was genuine.

  6. I just listened to him today, and introduced my kids to him...they loved "Mack The Knife"...my fave too!

  7. "Beyond the Sea" was one of my mom's favorites.

    Hey, Merry Christmas!!

  8. Thank you Pam great composition plus the live songs from Tom Jones Show which I had not seen before. We all love his lifetime of work and now pray for his Soul, especially at this time of the year. Merry Christmas & Happy New Year to all his fans.

  9. Hi Pam - Thanks for this nice tribute to Bobby Darin. He really was an incredible talent who accomplished so much in his tragically short lifespan. Several years ago I'd written a similar tribute to Bobby on his birthday and illustrated it with my caricature of him. Here's the link, as I think you might enjoy seeing the caricature since you're a big fan of his as I am:

  10. What a great, truly heart-felt tribute.

  11. Tho Bobby was THE best at being a talent in the entertainment world when it comes to how he treated his family ( no, not his only son Dodd) he never amounted to anything at all. Any man who has gathered great wealth and doesn't even have the guts to tell his mother let alone the rest of his family he's not going to even mention any of them by name in his will is a giant COWARD. Bobby made Joan Crawford daughter's book " Mommy Dearest " look like nothing. Again no one could touch the man on stage , recording etc... terrific talent came at a horrible price. Remember his family took care of him from day one. Who was with Bobby at the end, his stage manager, wife,lawyer, no people his sister. Sorry Kevin Spacey your picture got that wrong too.

    1. To me, unless you can qualify your accusations, there's no point in disparaging the man's memory. You could say how you know what you know without giving your identity, For example: Neighbor in East Harlem, high school acquaintance, co-worker, back-up musician, maitre-d in some Vegas or New York establishment, -- something like that might make your rant more credible.

  12. Yeah, those are Interesting comments from someone who has chosen to hide behind an anonymous profile.

  13. An excellent post. I had no idea about the Mensa and Connie Francis details.

    Darin's performance as the unlikeable racist in Pressure Point is indeed startling. I always wanted to see him play a private eye -- either the glamorous "Peter Gunn" type, or the more down-at-heel "Harry O" type, would have suited him.

  14. Thank you so much for making and posting this. I really wish I was born in another time so I could meet Bobby... But I am 25 years too late. He was the only entertainer /singer/ performer /actor that really caught my eye. And it will forever stay that way. - Shania Baker ( Annika1998beatles@yahoo.com) sorry didn't know what URL means....

  15. Thank you for the great post, really loved it. The #5 about Bobby and women gives me a little confusion. I know he did have a lot of women, but everything I have read about him implied or explicitly stated that he was faithful to Sandra-- and when he was divorced was when he really "played the field" (as well as before his marriages, that is my recollection? although we will never know). I do think he had unfathomable angst in his life and two things truly soothed his soul: (1)performing/entertaining and (2) the company of women.

    As for the commenter and references to "Mommie Dearest", these comments I find offensive-nobody should expect to inherit money out of some sense of entitlement. Whoever writes a "Last Will and Testament" is writing exactly what it is, THEIR last will and testament and they can draw it up any way they choose and include/exclude whomever they chose. Nobody said that life is fair, Bobby knew this all too well in the short time he was with us. I certainly don't have expectations of inheriting anything. So someone really needs to wake up that life is not fair, we are "never promised a rose garden", and especially not fair if you don't work to accomplish what you have set out to do (providing one has set goals in the first place). RIP Bobby !

  16. I fell in love with Bobby Darin when I was 4 years old. I thought he was so talented. At 5 years old I saw him at a restaurant in Malibu and was smitten.

  17. I sorta remember him as saying that his professional ambition was to be the Biggest Entertainer in Town by the time he was 30.

    So far as I'm concerned, He Was.

  18. Wonderful story. One of my favorite singers up there with sinatra.nat king colr

  19. Just saw Kevin Spacey play Bobby D. Great performance. Well done. Bravo!

  20. linda robertsonMay 18, 2017 11:14 AM

    bobby darin will never be forgotten in my world
    i wish i could of met this great man - i loved his style of musicand he was a awesome actor

  21. I wonder after watching the movie, Beyond The Sea, if his son ever considered doing DNA testing to see who his biological grandfather was. With Ancestry, it may be possible. I never knew the Bobby Darin story but enjoyed his music.

    1. Connie Francis says (in her new book) that Bobby believed his father was mob boss Frank Costello. Look him up. Definitely a resemblance!

  22. Absolutely riveting performer and artist extraordinaire, his personality and sense of humour never fails to brighten my days.

  23. Coolest guy this side of Dean Martin

  24. My first entertainer that I loved to watch, listen and try to imitate. He was remarkable and I've never seen anyone as gifted since. I'm glad I was fortunate to see these entertainers like Bobby, Frank, Sammy & Dean - I miss them all and listen to their music every day.

  25. When I was about 7 yrs My mother bought a scripto ink pen & they gave a 45 rpm record as a bonus & it had about 4 songs on it 2 on the front & 2 on the back the artist was Bobby Darin & 1 song I remembered my whole life was a song All by myself.I googled it & heard it again for the first time since childhood & it still sounds amazing.To me bobby was a singer/actor that followed the same template trajectory as Frank Sinatra.It was a sad tragedy to an immense talent,I only wish I held on to that 45rpm record of bobby.

  26. I had a fraternity brother who had the same situation with his heart as Bobby. He was also Italian. He made it through the surgery, but passed away the next day. When a group of us attended his funeral, I silently honored Bobby as well. I also felt a kinship to Waldon Robert Cassatto (Bobby's birth name), because the first five letters of Cassatto matched the first five letters of my last name. Bobby wrote, among others, a simple Country & Western song, "You're The Reason I'm Living". It remains one of my favorites. I originally resented Bobby's arrogance, which included him saying that he wanted to be a legend by the time he was 25. When I found out why, of course, I understood. He wrote and sang all different types of music, played a variety of instruments, hosted a TV variety show, did impersonations, acted in a serious movie and the bubble gum movies with Sandra Dee. I lived two towns in New Jersey from where so many of the rock'n'roll stars of the day would gather in Connie Francis' rec room. Her father hated Bobby, whose background was northern Italian. One of my favorite singers in the Alan Freed rock'n'roll concerts was Joanne Campbell, who was the greatest love of all of Bobby's relationships. Long live the memory of Bobby Darin.

  27. Hola Pam, Nico Ruiz cantó en el 2022 Mack the Knife, con esto, presentó a los jóvenes de hoy, algo de Bobby, aqui su presentación... https://youtu.be/coXl26Q2uFc


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