When Chet Baker sings My Funny Valentine, there’s little choice but to stop and just listen. His is the definitive version, and it’s infused with the understated intensity that defined his style. When Baker is at his best, which is often, nearly every note is exquisitely placed and leads to a mosaic of textures and sounds that only the most skilled and intuitive artists can reach. What’s even more amazing is that Chet Baker could do it with two instruments, his trumpet and his voice.

Yet there’s something decidedly enigmatic about the experience. He doesn’t knock you down with brilliant technique like Sinatra or lull you to a dream state with restraint like Stan Getz. He has an elusive quality, an ability to express, that may best be called "soul." To get to that point is not something one can set out to do. There must be context, a set of circumstances that shapes the work like practice and talent alone never could. And with Baker, to start to peel back the layers of his life is to get caught up in one of America’s most fascinating and tragic hard luck stories.

Chet Baker was born in Yale, Oklahoma on December 23, 1929. After some school and a stint in the Army, he started joining jam sessions in California while still a teenager and was a full-time jazz musician by the age of 21. He became a superstar while playing alongside Gerry Mulligan and was a major force in shaping the "West Coast" sound. After breaking with Mulligan, forming his own group and spending some time in prison on drug-related charges, he won the critics and readers polls in Down Beat in 1953, at the age of 23. At this time, the only thing that rivaled his talent was his good looks. A series of photographs from his early years by William Claxton reveal a camera-friendly star quality that no other jazz musician could touch. And then there were the drugs. By all accounts, Baker started early and had a voracious drug habit that often threatened his livelihood.

Up to a point, his story was perfectly scripted. The jazz James Dean—a talented kid from the Midwest with teen idol good looks and a thirst for strolls on the wild side. Dean is just one of a host of tempting comparisons. There’s also Hank Williams, Jimi Hendrix, Brian Jones, Keith Moon—any one of them would seem to do nicely. In these cases, logic, as shaped by tradition, dictates an early death. If that had happened, there is no doubt that his place in history would be with the others in the pantheon of fallen heroes. But Chet Baker didn’t die young. His death in 1988 at the age of 58 was nothing if not the fulfillment of prophecy, but for the rest of the world it was too little too late.

The list of mishaps he compiled is staggering. He lost his front teeth in a street fight in San Francisco and eventually had to be fitted with a denture, usually a death knell for horn players. He suffered through two broken marriages and a concurrent string of unsuccessful relationships. His inability to manage his financial affairs resulted in minuscule one-time payments for recording sessions that made far more for unscrupulous label executives. His drug addiction dogged him constantly, to the point where he not only spent time in several prisons and rehab centers but was persona non grata in Italy due to outstanding warrants.

The fall, jump or push out of an Amsterdam hotel window that marked his final tragedy was strangely, disturbingly, fitting. Yet, right up to that time, he was prolific. In fact, some of his best work was recorded in 1987. Despite this, he had been an exile of sorts for nearly thirty years, spending most of his time roaming through Europe and Asia. The American audience had tired of him by the late ‘50s, and although his albums continued to sell well, he had been stripped of star status.

There are tempting logistical explanations as to why this might have been. Baker himself stated that he preferred the European audience because of its respect for jazz as an art, rather than a commercial exercise. And jazz in America had moved into fusion, a style Baker never indulged. But these fail to resolve the central question: how is it that someone so perfectly American could produce such marvelous work for such a long time and yet die practically forgotten?

The real reason is that Chet Baker’s story is one of profound sadness. It’s simply too ugly, too sad, to romanticize. His addictions never consumed him, they were part of him. That’s the reason that a song like My Funny Valentine belongs so specifically to him. In his hands, it’s infused with an emotion and depth no other singer or player, not even Sinatra or Miles Davis, can match. He wore his heart on his sleeve in a body of work that stands as one of America’s most impressive jazz legacies. But the very thing that set him above his peers and made him a superstar also eventually damned him to obscurity.

For the American audience to embrace tragedy, it has to be coupled with innocence. James Dean remained a boy in death, allowing the collective mothering instinct to kick in. For the most part, that formula holds true across the board. But Baker’s story is more analogous to that of Jack Kerouac or William Burroughs, or perhaps most strikingly Marlon Brando—men who lived (or, in Brando’s case, continue to live) well into adulthood and, with some exceptions, continued to do inspired work. But a lack of repentance, or ability to repent, quickly makes a tragic hero ugly and thus impossible to embrace. In this process, some of our greatest creative artists get cheated out of their due.

Luckily, there are artifacts that shed light on the part of Baker’s life the broader culture chose to ignore. Late in life, he attempted an autobiography that, although it was never finished, has seen the light of day as As Though I Had Wings: the Lost Memoir. And shortly before his death, he was the subject of Bruce Weber’s documentary, Let’s Get Lost. Taken together, the two provide an enlightening window into the life behind the work.

That feeling is even more evident in Weber’s film. It’s one thing to read about Baker’s tenuous grasp on life and quite another to watch it unfold. Weber’s use of black-and-white cinematography is stunning and is a perfect complement to Baker’s fragile physical state. His face is wrinkled and worn far beyond his 57 years, and his energy is so low that he is barely audible. On one hand, it’s amazingly sad and almost painful to watch, but on the other, it’s quietly inspirational. His beauty is intact despite his haggard appearance, and he emits a quiet, dignified love of life and art. It’s impossible, really, to feel pity for a man who shows no signs of feeling it for himself. What’s left, then, is to marvel at the fact that Chet Baker milked his one life for experiences and productivity, which would more than fill two or three others together. The film has been out of print for some time, and it’s doubtful that it’ll ever come back. But there are copies around, and it’s absolutely worth the effort to track one down.

Baker’s funeral was sparsely attended and marked with little fanfare. Of his old friends, only pianist Russ Freeman showed up. And, with the exception of aficionados, his work is now essentially a footnote. Tellingly, Ken Burns’ much-vaunted documentary series Jazz makes little mention of Baker, except in connection with Mulligan.

While a few years of death generally do great things for a career, there may never be a perfect time for a Chet Baker renaissance. Nevertheless, Brad Pitt and Leonardo Di Caprio have both been rumored to play him on film so the time will undoubtedly eventually come. But before it does, there are ways to get a more nuanced appreciation of Baker’s life. His music remains some of the finest jazz ever recorded, and the memoir and film are valuable sources of context that are also interesting on their own merits. Chet Baker’s legacy speaks volumes about the world around it and serves better than any other to reflect our own values about the nobility of the suffering artist.