This is a story of astonishing natural talent, creative playfulness, sudden ascendance – and a slow, painful unravelling.
He was the American singer-songwriter who became The Beatles’ favourite U.S. artist, a man with a voice of breathtaking purity and flexibility, who could be tender one moment and hysterically funny the next. Yet for all his gifts, his legacy is shadowed by self-destruction: excess, damaged vocal cords, ruined finances, and a career that dissolved long before his life did.
Praise from the Beatles
Harry Nilsson didn’t come up through the usual music-industry channels. Born in Brooklyn in 1941 and raised largely by his mother in poverty, he became a bank clerk in his early twenties while writing songs at night. He sold his early compositions to other artists – including The Monkees – and gradually built a name among Los Angeles insiders. His breakthrough arrived not from a hit single of his own, but from something far more unusual: praise from the Beatles.
In 1968, during a press interview, John Lennon and Paul McCartney were asked who their favourite new American artist was. 'Nilsson', they both replied – without hesitation. (Nilsson himself had not yet met any of the Fab Four). Overnight, the music world turned its attention his way. When Lennon later called Nilsson at home, Harry thought it was a prank. It wasn’t. The endorsement transformed him from a respected songwriter into a star, almost by proclamation.
Effortless melancholy
And the talent backed it up. Nilsson’s voice was extraordinary: a clear, fluid, three-and-a-half-octave tenor capable of both intimate whisper and heroic, full-throated wail. It had the expressive warmth and flexibility of Paul McCartney’s – playful, emotionally direct, and stunningly beautiful at its peak. He didn’t just sing songs – he inhabited them.
On 'Everybody’s Talkin’ (famously used in the film Midnight Cowboy), Harry Nilsson's voice floats with effortless melancholy, capturing yearning without sentimentality. On 'Without You', his control is operatic, rising into a climactic, anguished cry that remains one of pop’s most astonishing vocal moments.
But Nilsson wasn’t just a voice – he was a natural storyteller with a childlike imagination. Nowhere was that clearer than in The Point! (1971), his extraordinary animated film and companion album about a boy born with a round head in a land where everyone else has pointy heads. It remains a gently profound allegory about difference and belonging, beloved by generations. The songs – particularly 'Me and My Arrow' – show Nilsson at his most generous and whimsical. He could be tender without being saccharine, funny without being frivolous.
The Hollywood Vampires
However, Nilsson’s life was already sliding into the orbit of excess. When John Lennon entered his so-called 'Lost Weekend' – a chaotic 18-month separation from Yoko Ono involving heavy drinking, studio conflicts, and late-night escapades – Nilsson became his closest accomplice. (The context: Harry was a key member of the infamous Hollywood Vampires, a celebrities' drinking club based at West Hollywood's Rainbow Bar and Grill. Alice Cooper convened the group: other core members were Ringo Starr, The Monkees' Mickey Dolenz, and The Who's notoriously hellraising drummer Keith Moon).
Together, Lennon and Nilsson terrorized bars, recording studios, and social circles in Los Angeles. They were thrown out of the Troubadour club in March 1974 for heckling. They were brilliant men trying to drink away pain, ego, and boredom. The irony is that while the stories (like being thrown out of the Troubadour nightclub) are hilarious on the surface, they were also the beginning of Nilsson’s decline.
During the recording of Pussy Cats (1974), produced by Lennon, Nilsson blew out his vocal cords. Legend has it he ruptured a vocal fold while trying to out-belt studio monitors; more likely it was years of strain and alcohol. Lennon begged him to rest. Nilsson refused. The voice that had once soared like McCartney’s now grew husky, frayed, and unstable. The transformation was devastating – not a stylistic shift, but a physical limitation. His later albums were uneven, erratic, full of flashes of genius but never again effortless.
A tragic London address
During the Seventies, Nilsson kept a London base at Flat 12, 9 Curzon Place – a stylish Mayfair apartment decorated by Ringo Starr’s ROR design company. Close to Apple Records and several nightlife haunts, it became a crash pad for musician friends while Nilsson worked frequently in the US. But it also became a tragic address.
In July 1974, Cass Elliot stayed there during her solo shows at the London Palladium; after a triumphant performance, she died in the bedroom of heart failure at just 32. Four years later, Keith Moon – who had been borrowing the same apartment – also died there at age 32, from an overdose of medication prescribed to treat alcoholism. Nilsson was devastated. Already uneasy about the tragedies, and spending more time in Los Angeles, he sold the flat to Pete Townshend. The apartment became a strange, sorrowful footnote to rock history: a home linked forever to two brilliant, lost voices.
Betrayal
The 1980s were unkind to Harry Nilsson. He released little music, and drifted out of the public eye. Worse came in the 1990s, as Nilsson’s later years were marked by a deeply painful financial betrayal. In the early 1990s, after years of stepping away from the spotlight to focus on family, Nilsson discovered that his longtime financial adviser and business manager, Cindy Sims, had been siphoning away his money.
She had access to his accounts and investments, and over time she quietly redirected funds, forged signatures, and made unauthorized withdrawals. By the time Nilsson realized what was happening, almost his entire fortune – millions earned from decades of songwriting royalties and hits – had vanished.
Nilsson took the case to court, but the legal fight was gruelling, expensive, and stretched over years. Though he eventually won a judgment, it came too late to restore what was lost. The emotional toll was equally severe: friends recall him feeling shaken, bewildered, and betrayed. Financial stress added strain to his already fragile health, especially after he suffered a heart attack in 1993.
Yet the loss also lit one last spark of creative determination. Nilsson, long retired from recording, returned to the studio in the final year of his life to work on new songs – determined, in his own words, not to leave the world quietly. He died in early 1994, before finishing the album, but the tapes were later restored and released as Losst and Founnd in 2019.
Heartbreak and joy: the Nilsson legacy
So what do we make of Harry Nilsson now?
He was, unquestionably, one of the greatest vocal talents popular music ever produced – a singer of extraordinary musical intelligence, capable of devastating emotional clarity and boundless play. His voice could be feather-light or thunderously full, capable of heartbreak without strain and joy without sentimentality.
In his finest recordings, you hear an artist who understood songs from the inside out: their architecture, their emotional pressure points, their humour and their ache. And while his career was tangled with excess, bad luck, and self-inflicted wounds, the work itself has outlived the dramas.
'Without You', 'Everybody’s Talkin’, 'One', 'Gotta Get Up', 'Don’t Forget Me' – these songs feel as intimate and surprising today as they did 50 years ago. They carry the clarity of confession, the ease of a storyteller, the warmth of a friend. If some of his potential was squandered, the part that remains is luminous, enduring, and deeply loved.
Five essential Harry Nilsson tracks
1. 'Without You' (1971)
Originally written by Badfinger (another great rock act with a tragic story), Nilsson’s version transforms the song into an emotional aria. His control, crescendo, and final, soaring wail remain one of pop’s defining vocal performances. A perfect meeting of elegance and devastation.
2. 'Everybody’s Talkin’ (1968)
A Fred Neil cover turned into haunting widescreen Americana. Nilsson’s vocal floats light and deep at once, capturing loneliness without despair. Its use in Midnight Cowboy made it iconic – but the performance earned that status on its own.
3. 'Me and My Arrow' (1971)
From The Point!, a gentle, melodic, deeply affectionate song about companionship and loyalty. Demonstrates Nilsson’s childlike wonder and gift for instantly memorable melodies.
4. 'Coconut' (1971)
Proof of Nilsson’s playful absurdism. A nonsense calypso story sung in multiple character voices. Completely unserious – but musically tight and brilliantly delivered. Shows the pure joy in his work. Famously used in Reservoir Dogs.
5. 'Gotta Get Up' (1971)
A buoyant ragtime-pop gem that hides melancholy under bright piano and bounce. Recently rediscovered via Russian Doll, it’s Nilsson at his most bittersweet – fun on the surface, heartbreak just beneath.
