Trumpeter and singer Chet Baker has the distinction of being a highly complex artist whose art was based almost entirely on simplicity. This Career retrospective provides a mostly illuminating view of his art and his contradictions, and it demonstrates why Baker was both a beloved and, ultimately, unexceptional jazz musician.

This compilation reflects the bifurcated nature of Baker’s career and talent. Disc One is devoted to Baker’s instrumental art. It is not a hit parade of jazz classics, and while there are some lovely moments that show what a lark it could be to dig jazz during the ‘50s and ‘60s, it also demonstrates clearly that Baker’s trumpet playing was always a facsimile of mannerisms from the greater and more distinctive players who Baker admired. Disc Two is more dramatic and distinct, focusing on Baker’s inimitable singing style. A love-it-or-hate-it commodity, Baker’s vocals were at least wholly his own. And occasionally they rose very high indeed.

The trumpet disc opens with the instrumental setting that introduced Baker to the world and that may have been his ideal: the piano-less Gerry Mulligan Quartet. Paired with Mulligan’s delicate and lyrical baritone saxophone in exceedingly clever arrangements, Baker’s minimal and direct style seemed like genius. On the iconic opener, “My Funny Valentine”, Mulligan plays harmonies around Baker’s plaintive reading of the melody, and it’s so well conceived that it feels like a complete jazz performance even without any significant improvisation. Some of other best stuff on the disc comes in the same form: a quartet reading of Miles Davis’ “Half Nelson” with Stan Getz in the Mulligan role, and then a Mulligan-Baker reunion from a 1974 Carnegie Hall concert that also features the old CTI rhythm section of that era.

Even in these few examples of Baker’s best stuff, you can see the problem. Two of these three are triumphs for Mulligan with Baker in tow. And two of the three are on tunes forever owned and defined by fellow trumpeter Miles Davis. It’s the Davis comparison, of course, that Baker cannot ultimately escape. It is not true that Baker sounds exactly like Davis. Rather, Baker plays constantly in the greater musician’s shadow, trying to achieve many of the same effects—lyricism or loneliness—with an utterly different (and less appropriate) sound. Where Miles invested “Valentine” with a complex set of emotions—darkness as well as a yearning—Chet just plays it really pretty and straight. Miles’s tone could be tart, piercing, lonely or coy and his rhythm was unpredictable, while Chet played a pleasant buzzing midrange across an almost old-fashioned swing feel. When this disc gives us Chet playing Monk’s “Well, You Needn’t” or a version of “When Lights Are Low”, you can’t help but make the odious comparison.

On a positive note, Baker is a natural assaying “Somewhere Over the Rainbow,” where his naïve tone works for him. His pairings with pianist Russ Freeman and saxophonists Bobby Jasper and Paul Desmond are also pleasing, as his fuzzy lyricism melds well with their slicker West Coast sound. But on all these tunes, for better or worse, we can hear evidence of Chet’s famous lack of training. He plays with a pure melodic sense, absolutely, but also without any sense of technical daring or innovation. In career that overlapped with those of Dizzy Gillespie, Clifford Brown, Miles Davis, Lee Morgan and Art Farmer among many others, Baker’s easy swing seems like an appetizer or maybe a dessert but hardly a whole meal.

As a vocalist, Chet Baker was a singular stylist. Like his trumpet playing but even more so, his singing is built on simplicity. Chet told friends that he sang with such focus and lack of embellishment because he was worried about his intonation. But at some point, Baker surely knew that he had become a star in large part because of his vocals. Introspective, sure, but also confidant, Chet developed his singing so that just a shiver of vibrato on the end of a phrase was like an elaborate improvised run from, say, Sarah Vaughan. On Disc Two of Career, tunes like “Let’s Get Lost”, “The Thrill Is Gone”, “It Could Happen to You”, and “My Heart Stood Still”, are stand-outs—with a still young Baker delivering riveting vocals against steadily swinging rhythm sections. Chet’s mystique, of course, was always tied up with his sexuality, as famous photo-shoots early in his career established him as both an androgynous icon and a model for a new kind of “sensitive” masculinity. His singing has both those qualities—a high, reedy voice that suggests female fragility on the one hand, matched by detached cool on the other. All by itself or before a bland orchestra, this vocal could seem like a one-note stunt, but with a great drummer as engine, it felt like tightrope work.

Just as the instrumental disc ends with some surprisingly strong tracks from the comeback phase of Chet’s career (after Chet spiraled downward on heroin and narcissism despite his fame), the vocal disc ends with a handful of gems. “There Will Never Be Another You” was a signature tune for Chet, and the live version here is a rarity I’ve never heard. This is followed by a live version of the tune that Elvis Costello wrote specifically for Baker, “Almost Blue”. It is chilling.

Finally, the whole shebang ends the way it started, with “My Funny Valentine”. I don’t much care for swelling strings in jazz, but this vocal performance is reminiscent of the late recordings of Billie Holiday—as much theater as jazz. Chet is clearly aware that any performance may be his last, and when he sings, “Is your figure less than Greek? Is your mouth a little weak? When you open it to speak, are you smart?”, it seems that he is singing about himself. You feel sorry for the guy—and that odd pathos is exactly what makes you realize the performance is a triumph. In short, this late, vocal “Valentine” has all the complexity that was absent from the 1952 trumpet line on the same tune.

This is a great way to end a collection that summarizes Chet Baker’s vexing career. A second or even third-tier jazz musician, Baker was a first class singer, at least some of the time. While there are single-disc vocal sets that I would urge you to purchase for the best of Baker, Career does a decent job showing the whole picture.