If a man truly were known by the company he kept, then Harry Nilsson would be a household name. Notoriously a friend of John Lennon, with whom he partied during Lennon's "Lost Weekend" of 1973-4, The Beatles were present throughout his life, even at his death. George Harrison sang and cried at his funeral. Ringo Starr was best man at his second wedding. At the start of his career, meanwhile, Nilsson received very public backing from John Lennon and Paul McCartney.
With that kind of endorsement, Nilsson's should have been a story with a happy ending. As it turned out, his career did not pan out as anyone - least of all Nilsson himself - might have expected. To listen to his catalogue, as collected here, is to hear enormous talent, a delightful voice, all driven by a not especially well-concealed ambition.
Nilsson's songs are literate, amusing, and often extremely moving, but his career was haunted by irony. A writer of great songs, his biggest hits (Everybody's Talking from 1968 and 1971's Without You) were written by other people. On achieving some success, his ambition almost instantly turned to complacency. Most cruelly, his last big payday came when RCA decided to arrest his expensive downward spiral and bought him out of his contract - essentially paying him to go away.
All of which, listening to the audacious brilliance of Nilsson at the start of his career, is nearly unimaginable. On his 1967 debut album, he covered Lennon's song, You Can't Do That, dropping into the song references to 20 other Lennon-McCartney compositions - turning a tough 1964 rocker into an affectionate homage to a Beatle-dominated world. For the soundtrack of Otto Preminger's film, Skidoo (collected on one of the three extras discs here), meanwhile, he delivered The Cast and Crew, in which he sings the credits for the entire awful movie. This is music of great accomplishment, but also huge playfulness, the work of an innocent talent in strange times.
Nilsson was not, however, as innocent as his voice and his arrangements often made him sound. Born in Brooklyn, New York to an alcoholic mother and soon-to-be absentee father, necessity made Nilsson resourceful. The Lennon biographer, Albert Goldman, called him "Harry the hustler", which isn't far wide of the mark. At only 15, Nilsson escaped to California and began reinventing his life: he managed movie theatres and sang on sessions for other songwriters. He wrote his own songs while he held down a job in a bank, working with computers.
"Harry was a genius, and a very motivated individual," his friend and collaborator Van Dyke Parks told me in 2008. "He mastered computers - which at that time required a great deal of abstract thought."
The songs Nilsson wrote, in a way, were also an attempt at escape from his early life. Within this compendious box set, collecting all the 14 albums Nilsson made for RCA between 1967 and 1977, you will find material to slake the thirst of any psychiatrist. From his debut album, there is 1941. Here, to a jaunty tune, the singer recounts his terrible upbringing and how he now finds himself repeating the sins of his father - himself deserting a wife and young child. His second album, Aerial Ballet, contains Daddy's Song, in which the singer's mother explains to him how an absentee father is technically a man - but also not like a man at all.
One of his earliest successful compositions was Cuddly Toy, in which an unromantic liaison is likened to a child's teddy bear. It tells you something about Nilsson's talents as a composer and his persuasiveness as a huckster that he sold this song to, of all people, The Monkees. Perhaps they weren't listening too closely. Nilsson's world, after all, is one which seems cute at first, but that on closer inspection proves to not really be that cute at all.
In 1970, Nilsson took his subversions to the screen, pitching an animated fable (with album soundtrack) called The Point. Featuring Nilsson songs and starring Dustin Hoffman, it's a story in which a young boy is sent away by his family because he is different from everyone else - physically and socially speaking, he has "no point". Throughout his career, Nilsson was someone desperate to escape into enchantment but ultimately unable to evade uncomfortable truths. His work is like a scientific fusion of Lennon and McCartney: one side wants to give you a nice tune and spare your feelings, while the other wants to lay it all out in the open and make you suffer.
It was an idiosyncratic approach, but in this, Nilsson was not alone. The songs of Van Dyke Parks shared Nilsson's interest in barbed melodicism, while Randy Newman was working on a similarly guileful blend of strong piano melody and slyly satirical lyrics. 1970's Nilsson Sings Newman, a genuinely wonderful album of covers (ending, of course, with Newman's So Long Dad), was a project to which Newman was objectively hostile - but that would be to reckon without Nilsson as a force of nature.
"Newman couldn't have been more revolted," Parks told me. "He saw Harry as an opportunist. But there was something undeniable about Harry and that was that he could sing, and sing incredibly."
Nilsson's career reached a commercial peak with albums that captured not just the essence of his music and his magnificent voice - but also something of that undeniable character. On his great 1971 album Nilsson Schmilsson, Harry successfully creates an image of himself as amiable philospher/savant/bum. He's witty, he's talented, he's emotionally vulnerable, and as the rather fragile-looking man in the bathrobe on the front cover testifies, he evidently likes a drink. He's having a good time and damn the consequences - a guy, in short, to have on your side in oppressive, Nixonian times.
The album's odd blend of morning-after anthems (Gotta Get Up; Early In The Morning) improvised jokes (Coconut) and uncharacteristically straight rock 'n' roll (Jump into the Fire), made it a great record, and a sheer masterpiece of apparent casualness. In fact, the events of Nilsson's later career proved it to have been a minutely-calibrated combination of his best qualities. When that balance shifted, and the heavy drinker gradually edged out the perfectionist and the charmer, things didn't go quite so well for Nilsson.
Not that the man was napping completely. No fool at marketing, he retained the successful Schmilsson tag for his next two albums: the solid Son of Schmilsson and the covers album A Touch of Schmilsson in the Night. Still, both in their way provided an indication of where Harry was headed. The former retains cleverness, and even some charm (Remember [Christmas] is lovely; The Lottery Song is another amiable fantasy life song). But it occasionally tips into a self-sabotaging vulgarity that testifies to the singer's impaired judgement and growing hubris. A Touch Of Schmilsson … , a collection of standards, is a charming album, but it has a tragic quality: it's like a photograph of a great beauty before a disfiguring accident.
For Nilsson, John Lennon was that accident - maybe more a perfect storm - and while their larks together in Los Angeles are the stuff of rock star legend, the limited advantageous exposure that Nilsson attained for himself in these escapades was at the expense of his most precious commodity. Pussy Cats, the rowdy album that Lennon produced for him, showed that Nilsson could still deliver deadly material like Black Sails - but his instrument, his voice, was shot.
The albums that followed, it's fair to say, do not seem to have fully held Nilsson's attention. He was not trying hard: he called one Duit On Mon Dei, (which is not Latin - he meant "Do it on Monday"), and released yet another covers record. When he did write, terrible would-be comic compositions like The Flying Saucer Song (from 1976's Sandman) make you wish he had stuck to covers - if only his voice could still carry them.
By the time of the final album here, 1977's Knnillssonn, Harry's voice had to a certain extent recovered. But for RCA, expensive albums filled with light-hearted music was a joke that had fatally worn thin. Still, his final album for the label offered a dignified exit, after a fashion. While his best albums feature a long cast list of celebrity musicians, Knnillssonn has no musician credits at all. Accidental or not, it's a grand closing statement. For all his famous friends, it's as if he's saying: "I got here on my own merits. I will go out on my own merits, too."
Nilsson died of heart failure in 1994, at age 52. He recorded only one more album after leaving RCA.
John Robinson is associate editor of Uncut and the Guardian Guide's rock critic. He lives in London.