To normals, his legacy is: writing (but not singing the hit version of) "One," singing the hit version of (but not writing) "Everybody's Talkin'", singing the hit version of (but not writing) "Without You'," and singing and writing "Lime In The Coconut." That's who Harry Nilsson is to my mom.
He had a fascinating, hyperactive, imperfect, productive music career besides/behind those pop peaks, and a somewhat unfair legend as a self-destructive bon vivant.
I'm not really gonna get into the bon vivant part. Other people can really break that down for you, down to the last gin and tonic. Let a man have a goddamn drink in peace is all I have to say about that. The man was not self-destructive. Self-subverting, maybe, but that's a lot more complicated than self-destructive. Self-destruction is just a search for the end, but self-subversion is a good way to outlive your legend, which, if you enjoy life for what it is, you're going to have to do at some point.
Anyways, about a year ago, I listened to his whole catalog, and I made a playlist of the songs I really liked. He's got some truly beautiful music and I really learned a deep respect for him.
His fanboys go totally out of control, mostly inspired by tangential lifestyle evidence, and compare him to Lennon and McCartney. This is crazytown and please do not drop $100 on a box set of music that will be that good. He is not the Beatles. But there is a crucial parallel in there... his ability to rep for musical styles and lyrical considerations thought to be obliterated by rock and roll, while remaining rock and roll in spirit, really does merit comparisons to Paul McCartney, and was his deeply humane genius. (My mind also goes to the great Lovin' Spoonful, to give it a crucially American context, in this regard.)
(In my book, and for this reason, his greatest single album is Nilsson Sings Newman, his reading of a bunch of Randy Newman songs with the man himself on piano. Randy Newman was the great modern throwback romantic curmudgeon, rock and roll yet totally not at all, and an ideal muse for Newman. The result is my second favorite duet record of all time, to Ella and Louis. It is the record that converted the skeptic in me.)
That's enough to generate a very rich and listenable 24-track spotify playlist, which I reach for whenever I'm in a bad mood or thinking about my troubles too much, and which I now present to you. Enjoy!