He Had Incredibly Bad Luck
American singer/songwriter Harry Nilsson was John Lennon’s favorite American musician—and yet many people have never heard his name before. One of the reasons was that Nilsson refused to perform on stage or TV, but another reason could be his extraordinary string of bad luck.
Three fatalities, a career ending medical emergency and a financial debacle all added to Nilsson’s reluctance to step into the spotlight and take his place in music history.
1. He Lost His Dad
Harry Nilsson was born in the Bedford–Stuyvesant neighborhood of Brooklyn on June 15, 1941. Little Harry didn’t have much time to enjoy a warm family life. When he was just four years old, his father got up and left the family. Nilsson was facing life without a dad to guide him.
But there was more misery waiting for Nilsson in his early life.
2. It Was A Miserable Childhood
The Nilssons were very, very poor. So poor, in fact, that young Harry Nilsson had to resort to eating dog food. Making matters worse was that his mother had issues with the bottle. It seemed as though like he had no chance at a normal childhood. Thankfully, his grandparents stepped in to help. He also had an uncle who encouraged him and taught him about music.
But something would soon get in the way of Nilsson’s music career.
3. He Got Fired
Nilsson’s family had very little money, so young Harry had to work to support them. He was still a teenager when he started working as a golf caddie. Sadly, Nilsson lost this job and paid a huge price. His family kicked him out of the house. He was 15 years old and needed a place to live. He moved to California and got a job at the Paramount Theater.
This theater would be a turning point in Nilsson’s life.
4. He Learnt To Play Instruments
Even though he was living on his own, Harry Nilsson was still too young to get into a bar—but he could get into underground hangouts where people played music. At one hangout he often went to, Nilsson received a gift from the manager. It was a plastic ukulele. It probably wasn’t worth much, but Nilsson put all he had into learning how to play it. At this time, he also learned to play the piano and guitar.
But fate was about to hand him a serious obstacle.
5. He Lied To Get A Job
In 1960, the Paramount Theater closed, and Nilsson needed a job. He had never finished high school, so this was going to be a challenge. Nilsson could have gone back and finished high school, but an easier solution was to lie on his resume. With his fake graduation information, Nilsson managed to get a job at a bank and found that he was good with computers.
But it wasn’t the typical double life of a musician.
6. He Lived A Double Life
Most musicians have to have a day job until they make it big. Strangely, Nilsson’s bank job was working on the computers at night when the bank was closed. This meant that music was his day job, and he had to make it work then. But finding a gig that paid in the daytime would be next to impossible.
And there was another problem.
7. He Had A Problem With The Words
Harry Nilsson managed to get gigs on his nights off, but he discovered a problem. He would often, and embarrassingly, forget the lyrics of the song he was singing. When this happened, Nilsson had little choice but to just sing whatever words came into his head. This gave him the idea to write his own lyrics.
For inspiration, Nilsson looked at his difficult childhood.
8. He Sang About His Pain
One of Nilsson’s first original songs contained lyrics about his sad childhood. In it, he wrote about the tragedy of his father heartlessly walking away from the family. He also included in this song a morose and fatalistic line about the future. He wrote, “And in 45, the mom and son were still alive. But who could tell in 46, if the two were to survive?”
Luckily, Nilsson’s life was on a trajectory very unlike this ominous one.
9. They Paid Him Next To Nothing
In 1962, Harry Nilsson took what he’d learned about singing from his uncle and mixed it with his natural skill, and got a job singing. His first job was with Scott Turner, and he was singing demos. For each track they recorded, Nilsson got just $5. It doesn't sound like much, but it was probably a lot more fun than working at the bank.
Nilsson’s songwriting career was also taking off.
10. He Was Getting Noticed
The following year, one of Nilsson's original songs attracted attention. He was working with John Marascalco, and they got a job writing a song for “Tutti Frutti” singer Little Richard. During the process, Little Richard got the opportunity to hear Nilsson sing.
When Little Richard heard Nilsson’s voice, he gave him a strange compliment.
11. He Sang “Good”
The voice that came out of Nilsson's mouth surprised Little Richard. It didn’t seem to match the way Nilsson looked at all. Little Richard then proclaimed, "My! You sing good for a white boy"! With this endorsement, it looked like Nilsson had a career ahead of him after all.
All he needed now was a label behind him.
12. He Hid Behind Aliases
Soon, Harry Nilsson was releasing singles, but for some reason, he hid himself behind various pseudonyms. He recorded “Baa Baa Blacksheep” as Bo Pete, and “Donna, I Understand” as Johnny Niles. This second single got him a contract with Mercury Records. Even though he was keeping his name out of the spotlight, his career was moving forward.
But he still needed a big break.
13. He Met An Angel
Nilsson cleverly began networking and managed to swing a lucrative deal: A gig working with the very influential Phil Spector. This led him to Peter Botkin Jr and then finally to composer and arranger George Tipton. It was with Tipton that things really took off. Tipton saw something in Nilsson, and he was ready to put everything he had on the line.
14. He Invested All He Had
Tipton was sure that Nilsson could be a star, and he put his money where his mouth was. He was ready to invest his life savings in Nilsson. Sadly, his life savings totaled to just about $2,500. It wasn’t a huge amount, but it allowed Nilsson to record four songs. Tower Records, a subsidiary of Capitol Records, heard the tracks and bought them up. It was a huge relief and the beginning of a partnership with Tipton.
With all this going on, Nilsson still found time for romance.
15. He Got Two Partners
In 1964, Nilsson married Sandi McTaggart, and two years later, he signed on with RCA Victor. So, he had McTaggart as his romantic partner, and he kept Tipton on as his music partner. His first album with Tipton was Pandemonium Shadow Show. Sales were slow, but the critics loved it. It also attracted the attention of people in the music business, including publicist Derek Taylor.
As it turned out, Taylor had some VIPs for friends.
16. He Passed Them On To Friends
Taylor was in his car waiting for his wife when he heard Nilsson’s “1941” on the radio. Taylor immediately ordered a whole case of Nilsson’s Pandemonium Shadow Show because he wanted to share them with friends. As it turned out, his friends went by the names John, Paul, George, and Ringo.
This was how the Beatles came to hear Nilsson’s work—and it would change Nilsson’s life forever.
17. It Was All About Them
Taylor was the press officer for the Beatles, and he soon turned all four of them into Harry Nilsson fans. But this wasn't so hard. You see, two tracks on the album were covers of Beatles songs: “She’s Leaving Home” and "You Can't Do That" . Nilsson also made references to 17 Beatles songs on the album. So, it wasn’t that hard for the Beatles to fall in love with Nilsson’s music.
With the Beatles as fans, the world would soon be hearing about Nilsson.
18. His Name Got Out There
At this time, John Lennon and Paul McCartney were busy launching their music company Apple Corps. At a press conference, a journalist asked Lennon who his favorite American musician was. To everyone’s surprise, Lennon said it was “Nilsson”, who was relatively unknown at this time. When they asked Lennon who his favorite band was, his answer was “Nilsson” as well.
This was about to get really, really big.
19. He Had One Odd Favor
With this incredible endorsement, Harry Nilsson was finally able to quit his job at the bank and focus on his music career. He asked RCA for a favor. He wanted his own office to work out of. This was an odd request, but it likely came from his days at the bank, where he also had an office. RCA happily obliged with this small favor, and Nilsson sat down at his new desk.
Then something strange started happening.
20. He Answered His Own Phone
Because of John Lennon’s comments, people were curious about this Nilsson fellow. So, now Nilsson’s new phone in his new office was ringing off the hook with various people wanting to talk to him. Most of the callers couldn’t believe that someone as famous as Nilsson would actually answer his own phone.
But some of the callers were famous as well.
21. He Got A Pair Of Surprising Phone Calls
While Harry Nilsson was taking calls from various people about his career, two of the callers stood out. Both Paul McCartney and John Lennon called to say that they really admired his work on Pandemonium Shadow Show. Apparently, Lennon had listened to the album for 36 straight hours.
But other callers had strange experiences with Nilsson.
22. His Answers Were Strange
Once the caller accepted that they were actually speaking directly to Nilsson, they started asking questions. Nilsson later said that most of the exchanges went like this. "When did you play last?" "I didn't." "Where have you played before?" "I haven't." "When will you be playing next?" "I don't."
Nilsson was hiding from his fans, and he had to do something about it.
23. He Made A Huge Mistake
Harry Nilsson hired a manager and started appearing on TV and shows in Europe. It might have been a dream come true—except it wasn’t. Nilsson didn’t like this side of the music industry, and he made the rash decision to only work in the studio. Years later, Nilsson would say this was a huge mistake.
This next decision would be a lot more successful.
24. He Got Chosen
Nilsson’s third album was titled Aerial Ballet, and it got its name from his great-grandfather’s Swedish circus act. One song on the album, “Everybody’s Talkin’,” was a minor hit in the US market, but then it got an unexpected boost. A year after its release, director John Schlesinger chose it for his film Midnight Cowboy.
No one knew it then, but this film was going to be a huge hit.
25. He Received An Award
Not only did Schlesinger want Nilsson’s recording of “Everybody’s Talkin’” for his film, but he also wanted the song to be the theme for the entire first act of the film. Midnight Cowboy went on to receive multiple awards including the Academy Award for Best Picture and Best Director. Nilsson managed to snag a Grammy for Best Contemporary Vocal Performance.
Whether he liked it or not, Nilsson’s name was now out there.
26. He Turned Down A Profit
The Beatles had brought a certain amount of fame to Harry Nilsson. But his song for this award-winning movie sent Nilsson’s celebrity into overdrive. Scott Turner, who, back in 1962, had paid Nilsson a measly five dollars for singing demos, wanted to make this right. He offered to pay Nilsson what he felt he owed him. Nilsson told Turner that he had already paid him five dollars a song and that was enough.
Nilsson would soon regret saying no to free money.
27. He Hit The Charts
By 1969, Harry Nilsson was on to wife number two. This was Diane Clatworthy, but she must have been wondering what she had married into. You see, Nilsson still hadn’t reached the charts with an album. That all changed with his album Harry. It hit the charts, and his single, "I Guess the Lord Must Be in New York City" was a Top 40 hit.
He also decided to take a huge risk on an up-and-coming composer.
28. He Got Obsessed
Before Randy Newman was an Academy Award-winning composer, Harry Nilsson covered one of his songs. After this, Nilsson made the strange decision to do an entire album of Randy Newman songs. While it was a commercial failure, Stereo Review magazine named it record of the year and Newman’s career took off.
But it was Nilsson’s career that needed a jump start.
29. He Put “De Lime In De Coconut”
Nilsson’s seventh album, with the silly title Nilsson Schmilsson, ended up being his most successful. He received a nomination for Album of the Year at the Grammys and won Best Male Pop Vocal Performance for “Without You”. It was on this album that Nilsson also sang the often-repeated and silly sounding line: "Put de lime in de coconut, and drink 'em both up".
With a hot album out there, people were now really wondering. Will we ever see this guy perform?
30. He Was Heard But Not Seen
Harry Nilsson was becoming more and more popular, and this made it even more odd that he wasn’t appearing on stages or TV screens anywhere. Fans certainly wanted to see him, but Nilsson seemed content to stay hidden. People started calling him the "singer-composer who is heard but not seen"
Maybe this explains why he decided to star in a movie.
31. He Did A Spoof
After the huge success of Nilsson Schmilsson, there was pressure to back it up with another successful album. But Nilsson didn’t seem to like pressure, so he decided to put out an eccentric album. Son of Schmilsson included some songs spoofing horror movies, and both Ringo Starr and George Harrison.
Next, Nilsson would go from spoofing horror movies to starring in one.
32. It Was A Horrifying Coincidence
Just a short time after Nilsson had worked with Starr on his horror-themed album, Nilsson got a call from Starr asking him to work on a horror movie with him. You couldn’t blame Nilsson for thinking that his horror spoof album had inspired Starr.
As it turned out, it was a total coincidence.
33. It Was Going To Be Fun
Starr had decided to make a horror musical, and he convinced Academy Award-winning cinematographer Freddie Francis to direct. Starr wanted Nilsson to play Count Downe, and other musicians, like members of The Who, Led Zeppelin, and Peter Frampton, were also appearing.
Making the film sounded like it would be a lot of fun. As it turned out, it was not a barrel of laughs for audiences.
34. He Was In A Dudi
Son of Dracula did not do well. Critics didn't like it, and didn't get much of a release. Starr once said that he had a VHS copy of the film but couldn’t muster up the courage to watch it. To try and forget the tragedy that was Son of Dracula, Nilsson went on a spectacular bender with a very famous young man.
35. He Had A Good Time With John
Around this same time, Nilsson was hanging out in California with a newly separated John Lennon. The idea was for Lennon to produce Nilsson’s next album. Instead of producing an album, the pair produced a good time. The two engaged in some pretty heavy drinking, and then they got into a very embarrassing situation.
36. He Got Thrown Out
While Nilsson and Lennon were partying, they found themselves at the LA club the Troubadour. On stage was the comedy duo the Smothers Brothers, and Nilsson and Lennon decided to vocally show their disapproval of the show. The heckling got out of control, and security had to throw Nilsson and Lennon out of the club.
This next situation wouldn’t be so easy to forget.
37. It Hurt Real Bad
Nilsson and Lennon did finally get their act together and started working on Nilsson’s album. But there was a snag. While working in a jam session that also included Paul McCartney, Nilsson hurt his throat really badly. Too embarrassed to say anything, Nilsson powered through the session.
But he would pay for this big time.
38. He Lost It For Good
The album that Nilsson and Lennon came up with was Pussy Cats, and they used the name as an explanation for all their bad behavior while in LA. Unfortunately, it became clear on the recording that Nilsson had done serious damage to his vocal cords. Friend and former member of The Monkees, Mickey Dolenz, opined that Nilsson never got his voice back after this incident. It sounded like the end of his career.
It was nothing that a new marriage couldn’t fix.
39. He Saw Her In The Window
In 1967, Nilsson’s marriage to Diane Clatworthy ended, and he needed a replacement. Two years later, he was walking down the street in New York City and happened to look into the window of an ice cream parlor. There was a woman working there who made Nilsson stop cold, even without an ice cream cone in his hand.
Nilsson went in and told her she was the most beautiful girl he’d ever seen.
40. He Bowled Her Over
The woman in the ice cream shop was Una O’Keeffe, and she was from Ireland. She was not easily swayed by Harry Nilsson, but suggested he bring her flowers and a melon to woo her. Nilsson did just that, but shocked her by showing up with them in a limousine. O’Keeffe couldn’t believe her eyes.
He’d won her over.
41. It Was Marriage Number Three
Soon after the stunt with the flowers, melon, and limo, Nilsson was marrying a pregnant O’Keeffe. Bestie Ringo Starr stood up as his best man and even brought an entire tray of wedding rings from Tiffany & Co to the occasion for the happy couple to choose from. The two would go on to have six children.
It was a wonderful day, but there was more tragedy in store for Nilsson.
42. His Lived In A Jinxed Apartment
In the 1970s, Harry Nilsson was residing in a two-bedroom flat in the Mayfair district of London. When Nilsson was away, he lent it to the Mamas & the Papas singer Cass Elliot. After a particularly demanding performance on July 29, 1974, Cass tragically had a heart failure and died right in Nilsson’s apartment.
But this wasn’t the only time.
43. Lightning Struck Twice
In 1978, The Who’s drummer Keith Moon wanted to rent Nilsson’s Mayfair apartment. Nilsson hesitated because he suspected the apartment carried a curse. Moon’s bandmate Pete Townshend told Nilsson not to worry. After all, "lightning wouldn't strike the same place twice". Boy, did he get that wrong. On September 6, Moon’s girlfriend discovered his lifeless body in the same room where Eliot had passed.
A distraught Nilsson sold the apartment and moved to LA.
44. He Retired
Back in 1977, Harry Nilsson left RCA. He was angry because they’d had the gall to release a Greatest Hits Collection without even letting him know. He tried following in Randy Newman’s footsteps and worked on a film. Robert Altman’s Popeye was a disappointment, and some critics even pointed out Nilsson’s score as part of the problem. After this disaster, Nilsson started calling himself “retired”.
But there was more heartache coming his way.
45. He Lost A Friend In A Tragedy
On December 8, 1980, Harry Nilsson faced a gruesome calamity. His friend and occasional collaborator, John Lennon, tragically lost his life. Nilsson, who always avoided the spotlight, joined other protestors to support gun control. He even sang “Give Peace a Chance” with the Beatlefest band called Liverpool.
Ten years later, Nilsson would face a financial tragedy.
46. He Desperately Needed Money
In 1990, after a failed attempt at a production company, Harry Nilsson found himself in financial difficulties. When he turned to his financial advisor for some much-needed cash, he got some very horrible news.
47. He Lost It All
Nilsson’s financial advisor, Cindy Sims, had absconded with all the money he had earned as a recording artist. Suddenly, this successful songwriter and recording artist had only $300 in the bank and was also facing a huge debt. At least they caught the culprit, and she could pay him back.
Well, that didn’t quite happen.
48. She Got Off Easy
Harry Nilsson had basically caught his financial advisor, Cindy Sims, red-handed. Strangely, her punishment was extremely light. She spent two years behind bars and didn't have to pay back a single cent. In 1992, Nilsson did one final concert with Ringo Starr, where he sang “Without You,” the famous Badfinger song he’d once covered that contained the line: “I can’t live if living is without you”. Maybe he was singing about his money. Chillingly, two members of Badfinger had taken their own lives—one after a financial manager had stolen all of the band’s money, and the other after a dispute over royalties for “Without You”.
Even without a nest egg, Nilsson seemed ready to fully retire. Sadly, he didn't have much time left to enjoy it.
49. He Said Good Night
In January 1994, Harry Nilsson surprised everyone and came out of retirement to make an album. One night during this time, he and his wife were at home watching a movie. O’Keeffe got up to go to bed, and Nilsson told her how much he loved her. The next morning, O’Keeffe woke up to find Nilsson’s cold, lifeless body beside her in bed. His final album received the title Losst and Founnd.
Nilsson seemed to have spent his life in hiding, even from his son.
50. He Left A Legacy
Nilsson’s father had walked out on his family, and in a way Nilsson had done the same thing. Zak was Nilsson’s only child with his second wife, and he had very little contact with his dad. It was like history had repeated itself. But Nilsson changed all that when, in 1991, he took his forgotten son on a trip to London. Zak went on to become a musician, but sadly passed from cancer in 2021.
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