Aerial Ballet is available on its own, but it also comes packaged on an import CD with Pandemonium Shadow Show and Nilsson’s odd 1971 re-imagining Aerial Pandemonium Ballet, for which he remixed and combined songs from both albums in an attempt to bring new attention to some old material following the success of “Everybody’s Talkin.’” The entire double-disc set makes a fine Nilsson starting point, especially since it adds the Aerial Ballet outtake “Miss Butter’s Lament,” another allegorical character sketch that Nilsson co-wrote with Bob Segarini for the band The Family Tree.

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Next steps: Also packaged together on an import CD, 1969’s Harry and 1970’s Nilsson Sings Newman show Nilsson stepping back from contemporary pop and embracing Tin Pan Alley. Between the covers of “Mr. Bojangles” and “Mother Nature’s Son” and the retro-flavored originals “Open Your Window” and “Marchin’ Down Broadway,” Harry aims to evoke the simplicity and directness of the old-timey. As for Nilsson Sings Newman, on the surface it appears to be an even simpler record, featuring a handful of Randy Newman songs covered by Nilsson (with Newman accompanying). But at that point in his life, Nilsson was as entranced by the possibilities of the studio as he was by the possibilities of minimalist piano ballads, and so he recorded track after track and take after take, sometimes splicing together the choicest seconds of a recording, and sometimes leaving in booth chatter and mistakes. The result is an album that’s both beautiful and strange, putting Newman’s songs in the context of Nilsson’s unique sonic environments.

By 1970, Nilsson was still mainly a cult act, responsible for a couple of fluke hits of his own and a couple of big hits for other people. His early recordings had been eclectic and eccentric, taking his natural talent for melody and his strong, multi-octave voice and using them as elements in songs and albums that took a little work for fans to fully follow. Nilsson then began wading into the mainstream by writing the story and recording the soundtrack to the 1971 animated ABC movie-of-the-week The Point!, a fable about a round-headed kid named Oblio who lives in a kingdom where everyone and everything has a point—even Oblio’s dog, Arrow. The special and its music are both a little strained and cutesy, but they’re fleetingly brilliant, and feature some of Nilsson’s snappiest and trippiest songs since his debut.

Later that year, Nilsson released Nilsson Schmilsson, the epitome of the ’70s “well-made album,” deploying state-of-the-art production on a set of originals and covers that show stylistic versatility, with an impressive amount of care lavished even on the filler. But while Perry kept Nilsson on-task in his pitch to a wider audience, Nilsson didn’t leave his wit or fancifulness behind. Songs about moonbeams, traffic, and waking up from a hangover take up as much of the record as the massive pop hits.

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Nilsson could’ve easily continued down the Nilsson Schmilsson path and banked piles of money. Instead, he reunited with Perry for Son Of Schmilsson, a wildly offbeat rock record that opens with the perverse “Take 54,” a song about a pop star who can only sing his “balls off” when his favorite groupie is in the booth. From the vampire picture on the LP cover to jokey tracks like the country music parody “Joy,” the bed-wetting PSA “I’d Rather Be Dead” (featuring a chorus of the elderly), and the crude “You’re Breakin’ My Heart” (with its chorus “so fuck you”), Son Of Schmilsson is about as flippant a response to fame as any platinum-level artist has ever attempted. Writing about Son Of Schmillson in 1972, Rolling Stone critic Stephen Holden dismissed the record as a whole for having “a humor so deadpan, so essentially sarcastic, that it is difficult to relate to it on more than a superficial level,” adding, “Life is just a silly, meaningless jumble of dreams and memories, OK—but where is the hurt and disappointment that infuses such a vision?” Yet only an artist as hurt and disappointed as Nilsson had been all his life could’ve recorded an album so defiantly un-smooth. And even with its kinks, Son Of Schmilsson features songs like “Remember (Christmas)” and “Turn On Your Radio,” as lovely and moving as any pop music of their era.

Son Of Schmilsson became the model for Nilsson’s ’70s albums, which frequently sport oddball cover art, twisted remakes of rock classics, and outright novelty songs like “Kojak Columbo,” “The Flying Saucer Song” and “Jesus Christ You’re Tall.” But sprinkled amid the more out-there material are some of Nilsson’s most heartfelt ballads, like the mournful cycle-of-life lament “Salmon Falls” and the quietly desperate “Don’t Forget Me,” and some of his most effortless pop songwriting, like “Pretty Soon There’ll Be Nothing Left For Everybody,” a jaunty song that maintains Nilsson’s preoccupation with cheerful nihilism. In a way, the ’70s albums—often knocked out during long benders, with Nilsson’s voice ravaged by misuse—are “well-made albums” too, in that they showcase a variety of styles and an expansive sound. There’s just something a little off about them. Maybe it’s that the creative force behind the music is a man gleefully sabotaging himself through self-destructive behavior and a love of bad jokes.

That said, while the post-Schmilsson records are probably best picked through for their best songs, fans who want to follow Nilsson to the edge of drunken madness are advised to spend some time with 1974’s Pussy Cats, Nilsson’s boozy, at times almost avant-garde collaboration with John Lennon, and 1975’s vastly underrated Duit On Mon Dei, which contains some of the most hummable and high-spirited music from Nilsson’s binge years. And though it’s not readily available, Nilsson’s soundtrack to Robert Altman’s 1980 big-screen version of Popeye (with songs arranged by Van Dyke Parks and sung by the cast) returns to the clean tunesmithery of Harry and The Point. All this work is so full of life at its highest and lowest that they make the conventional wisdom that Nilsson squandered his gifts seem churlish and industry-driven. He may have stopped making hits, but Nilsson never stopped making art.

One Nilsson scholar who buys the “what a waste” myth is John Scheinfeld, whose documentary Who Is Harry Nilsson (And Why Is Everybody Talkin’ About Him?) still rewards any fledgling Nilsson fan’s time, if only for the wealth of footage from TV appearances and recording sessions. Scheinfeld also locates the roots of Nilsson’s thorny gifts in his impoverished upbringing, which led him to develop a knack for entertaining himself while hustling to get by. For all its flaws, Who Is Harry Nilsson does make the case that in an era of inventive, knowledgeable songwriters like Brian Wilson, John Lennon, Van Dyke Parks, and Randy Newman, Nilsson became the musician’s musician, admired for his wild arrangements, his insistence on satisfying his own muse before making his record label happy, and his willingness to mock himself, the culture, and every notion of showbiz propriety.

Where not to start: Nilsson’s late-’70s albums aren’t as awful as their reputation, but the ratio of buried gems to time-wasters is way out of whack. Similarly, the 1968 soundtrack to Otto Preminger’s wackadoodle comedy Skidoo is easier to admire than enjoy, though Nilsson’s singing of the movie’s credits is a clever stunt that every fan needs to hear at least once (if only once).

But the Nilsson album that neophytes should most definitely avoid is one of his biggest (and most surprising) hits: A Little Touch Of Schmilsson In The Night, a collection of standards that provides one of the best showcases for Nilsson’s remarkable voice, but is so slow and syrupy that it actively impedes pleasure. The record is way too reverent—a word rarely applied to Nilsson.