At New York City’s Birdland this past March, pianist Andrew Hill accepted Playboy‘s Artist of the Year Award, smiled for the cameras and then, without a single announcement, spent an hour filling the room with his distinctive, slightly deteriorating brand of pianistic alienation. On the title track from his recent Time Lines, Hill pounded away on an F major chord while drummer Eric McPherson thudded swirling rim shots with a meandering calypso backbeat. Hill’s attack definitely swung, but in a perplexing direction: Unlike Herbie Nichols, Randy Weston and other Monk-inspired pianists, Hill left fewer rhythmic and harmonic signposts, striking when you’d least expect. Perhaps aware that he was leaving listeners adrift after accepting a plaque from Hefner’s empire, Hill, who never plays anyone’s standards but his own, began playing the opening motif from Meyer and Caeser’s 1928 “Crazy Rhythm.” The drums played against the piano and the bass repeated an off-kilter Latin beat, but Tin Pan Alley was somewhere buried in the subtext:

Crazy rhythm, here’s the doorway. I’ll go my way, you’ll go your way. Crazy rhythm, from now on We’re through.

Hill’s playing wasn’t up to his 1960s peak–it was actually rougher than on the CD–but it was better to be honored belatedly than not at all. Many rapt audience members were trying hard to follow the clangor, nodding their heads and trying to take it in. It was a clever moment, a rare nod to accessibility in an extremely opaque evening.

In a break from critical orthodoxy, I pondered the fine line between complexity and incoherence. Sometimes Hill pounded the keys with purpose. Other times, he seemed to be fumbling for the right notes. Crazy rhythm, indeed. The announcement last year that Hill had signed with Blue Note for the third time was a major event in the jazz world, but it was also bittersweet: He was battling cancer without health insurance and needed the money only a major label could offer, composing and playing furiously through his illness and treatment. But the fuss and awards surrounding Hill’s recent deal were really all because of what he did during his first stint on the label beginning in 1963.

Back then, Hill was 21 and telling everyone that he was a Haitian protégé of the neoclassical composer Paul Hindemith. In fact, he was a native Chicagoan whose studies with Hindemith were more like an ad hoc correspondence course; the fledgling Hill approached the eminent composer after a performance, the two men exchanged some letters and Hindemith died the year Hill got his record deal. Hill’s biographical discrepancies continued. Various sources credit him with a PhD in musicology from Colgate, but it turned out that Colgate never offered that degree to anyone. Jazz musicologist Lewis Porter did some investigation on the matter a few years ago, and a Colgate professor sent Porter an e-mail from Hill, who said that he didn’t want credit for something he didn’t do and added that jazz critics don’t do enough of their own research and should do everything possible to stop the lie. Of course, Hill’s first few years of recording are worth more than a stack of doctorates, and even if he didn’t write a dissertation of his own, he certainly provides enough material for someone else’s.

Is Hill a genius, a trickster or a con artist? To ask the question is to answer it: all of the above. Tall tales have long been a part of the greatest jazz legends. Who really believed that Louis Armstrong was born on July 4, 1900, or that Jelly Roll Morton invented the music? Behind the self-mythology, though, the music is even harder to unravel. Following Hill’s biographical claims may be tricky, but following the transcriptions of his compositions is even more baffling, and this is a difficulty he can own. In 1963 the Beatles hadn’t yet conquered America; free jazz was still relatively new and divided the lines of the Blue Note roster. Saxophonist-composer Joe Henderson was still carrying the torch for accessible swing, digging into the Latin groove that took Stan Getz to the pop charts. Multi-reedist Eric Dolphy was arguing with his leader, Charles Mingus, on the bandstand through musical dialogues, and he pushed further into the harmonic stratosphere with every transgressive wail. Tony Williams, then a 17-year-old wunderkind who had picked up a seat in Miles Davis’s quintet after seeming to memorize every beat thudded by Philly Joe Jones, was unable to ignore something freer rumbling from the harmolodic territory of Ornette Coleman and the rattle of Billy Higgins’s high hat. Amazingly, Henderson, Dolphy, Williams and Hill, along with trumpeter-arranger Kenny Dorham and bassist Richard Davis, all came together on March 21, 1964, to record Point of Departure, and in a single day Hill made a jazz masterpiece. It was his fourth album for Blue Note, and the first three, Black Fire, Smokestack and Judgement, had also been recorded in single-day sessions in the previous four months of frenetic activity. The recording would also be Dolphy’s last studio session; that June, he would be dead at 36, and everything that he recorded in those last few months would be scrutinized and pondered in search of a future jazz never quite had.

Point of Departure routinely makes critics’ all-time-favorite jazz album lists, but Hill’s compositions are rarely played on the bandstand or heard from conservatory practice rooms. A look at the chart for “Refuge,” the first track on the album, explains why. On the recording, Dorham and Hill are playing the melody, while Henderson throws in an empathetic harmony and Dolphy offers an alto dissent. Somehow, Hill’s composition unites these three divergent styles, with Henderson and Dorham playing the changes and Dolphy literally going off the charts. Hill’s jagged comping and peripatetic lines are anchored in a Monkian percussive hiding place, a refuge of sorts. But the chart itself offers less of one. It’s harder to play than anything by Wayne Shorter, who made his own Blue Note debut the same year. Shorter, who can be heard from conservatory to conservatory and bandstand to bandstand, may have earned the nickname Mr. Weird, but his madness made a kind of divine sense; no one else could have thought of tunes like “Juju” or “Speak No Evil,” but once you learn them, they are indelible. Hill doesn’t let you in nearly as easily. Look at the chart, lose your place, start over and marvel at those who can do it well; improving on the album is impossible anyway. The track that followed was named by Frank Wolff “New Monastery” as a nod to Thelonious Monk, but Monk’s terrain is a much less difficult path to follow. You hear Monk in Hill’s attack, but the harmonic stratosphere is something more dense and even more strange. “New Monastery” wasn’t Hill’s title anyway. He once said that everything he ever wrote came out of a Kenny Drew blues motif he heard once–but then, Hill has said many things.

Point of Departure is confounding, but it is a text, with heads and solos followed in bop protocol, something that Dolphy’s Out to Lunch, recorded in the previous month, defected from more dramatically. Ornette Coleman’s Live at the Golden Circle, John Coltrane’s First Meditations and Cecil Taylor’s Unit Structures would stray further from the written lines. (“Where are you Bud?” wrote Taylor in the liner notes, giving a stream of consciousness shout-out to Bud Powell. Many would have answered, “Far, far away.”) Hill would become more accessible on other occasions. “Catta,” the lead track from vibraphonist Bobby Hutcherson’s extraordinary 1965 album Dialogue, is a Hill composition that sounds like a cousin to Joe Henderson’s “Recordame,” a Latin soul jazz number with a centered groove and a catchy hook. “Catta” was recorded a year and a half after Blue Note artist Lee Morgan made a crossover score with a similarly infectious Latin composition, “The Sidewinder,” which hit No. 25 on the Billboard chart and made it all the way to a Chrysler commercial in the 1965 World Series. If Hill had written more tunes like “Catta,” maybe he wouldn’t have asked each reader of Down Beat to send him a dollar the following year; it would be four decades before Playboy paid its respects.

Ironically, some of the most accessible Hill material from his first Blue Note run didn’t make it out of the vault until recently. Blue Note realized it was sitting on collectors’ items and belatedly released Hill’s work from the end of his first run with the label. This, too, is a case of better late than never. Passing Ships topped many jazz critics’ lists for 2003, even though it was deemed unreleaseable in 1969. The sessions that Hill recorded that year with strings are especially noteworthy: haunting, lovely, complex and without a trace of Third Stream preciousness. “Illusion,” from the Mosaic Select box set, is driven by the slow, steady, swinging march of Mickey Roker’s drums. Hill, who had jumped from chord to chord on the compositions that made his reputation, slowed down for a simpler progression. Bennie Maupin blows some tasteful tenor lines with a kind of Lester Young-inspired melodic economy, and the strings are arranged enough for chamber and loose enough for jazz; the cello tugs and takes you in deeply. The rest of the sessions are like a dream. They sound nothing like the commercially viable jazz of 1969–they might as well have been recorded in a different century from the one that produced Miles Davis’s Bitches Brew, and it’s certainly a better jazz session. But Hill never made the commercial crossover, just the counterintuitive, deft ones that spelled career suicide–until recently, that is.

Another pianist who made his Blue Note debut in the early 1960s, Herbie Hancock, was more of a playa. Like Hill, Hancock was a Chicago native who had a classical connection (he played with Rafael Kubelik and the Chicago Symphony when he was 11). But Hancock also had a Top 10 hit early on with “Watermelon Man” (not his own version, but still), and while honing an original, complex and deep pianism always had his eye on what the popular audience wanted. It would be hard to imagine Hill pitching Bose speakers or tinkling impressionistic lines behind Christina Aguilera on the Grammy Awards. Two roads diverged.

Hill spent the next three decades paying dues. In the liner notes to his From California With Love (Artists House, 1979), Hill wrote, “At the zenith of my Blue Note recordings, I found that fame and fortune were not my reward, but fame and poverty. This was hard to believe, for I had seen artists like Miles Davis, Maynard Ferguson, Oscar Peterson, etc., pass through Chicago. They weren’t surviving but living.” Yet Hill wouldn’t make concessions to live a little better, and he preferred teaching in California prisons to playing on pop sessions. Even a second run for Blue Note in 1989 and 1990 didn’t last beyond two albums, both regrettably out of print, and somewhere along the line his piano technique, never especially smooth, became less consistent. You weren’t exactly sure if that was how he meant to hit those keys or if he missed them. But he achieved some triumphs late in his career, some wholly distinct from that initial burst of greatness from 1963 to 1967. Dusk (Palmetto, 2000) was originally conceived as a tribute to Point of Departure for a gig at New York’s Knitting Factory. But the resulting CD sounded nothing like the album that inspired it. It was a musical interpretation of Jean Toomer’s 1923 masterpiece Cane, with a title alluding to the opening stanza of Toomer’s Harlem Renaissance classic:

Her skin is like dusk on the eastern horizon. O cant you see it, O cant you see it, Her skin is like dusk on the eastern horizon.. . When the sun goes down

The CD matched Cane for lyricism with a sharp edge, achieving a quiet beauty the younger trickster of the 1960s didn’t quite reach when frantically jumping from chord to chord and interval to interval. The title track, which opens the CD, returns to a dominant groove plucked out on Scott Colley’s bass, while the horn lines travel in odd directions and Hill’s piano lines give contrapuntal retorts. A Beautiful Day (2002) lives up to its title, even more ambitious than Dusk in its orchestral scope, demanding, powerful and lyrical. Hill and an audience, albeit a specialized one, could finally meet.

Time Lines doesn’t quite reach the heights of those two recordings, but it has quiet and subtle powers of its own, even if they didn’t make the transition from the recording studio to the stage at Birdland in March. Hill’s rough beauty has inspired a generation of younger pianists like Vijay Iyer and especially Jason Moran, who combines a Hill-inspired attack with a Hancock-inspired crossover savvy, and who has identified himself as a Hill disciple, performing in deferential duets with him. But Hill’s recent impact has been in the jazz compositional landscape, and his twists and turns now seem less bewildering than they did in that frenetic period forty years ago. Altoist-composer Greg Osby, who performed beautifully on Hill’s first reunion sessions with Blue Note, has cited Hill as his greatest influence, and when they played together on The Invisible Hand (2000), it was not only a signal of Hill’s return to the label where it all began but a moment when Hill seemed less like an eccentric cult figure and more like an elder statesman. On Hill’s “Ashes,” that CD’s lead track, the chord sequences are still hard to follow, but Hill’s softened accompaniment and Osby’s breathy alto, complemented by guitarist Jim Hall’s lush lines, make it clear that the twenty-first century will finally be a time when Hill’s challenging conceptions will go down a little easier, less cryptic but as fascinating as ever. As Hill is enjoying his third act, those rhythms don’t sound quite so crazy anymore.