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I remember when I first heard it. I was like, Is this some kind of gag? Hipster irony avant la lettre? No one can really think this is good; is it like it's so bad it's good?
Now, much of my fondness for the music stems from fond memories of the person who introduced it to me and the situation at the time, which was rather ... um ... well I'll leave it there.
However, I now actually think it is good music. His rendition of Funny Valentine is gold.
"So, while most jazz albums of the period include, at best, five long instrumentals, Chet Baker Sings is made up of eighteen two-and-one-half-minute cuts—played and sung without any of the popular signifiers of "jazz expression." There is no vibrato, no "beautiful" singing, and no "strong" statement. There are no extended solos, no range dynamics, no volume dynamics, no tempo dynamics, no expressive timbre shifts, no suppression of extant melodics, no harmonic meandering, no virtuoso high-speed scales, and, in fact, very few sixteenth-notes—none of that stuff, in short, that told jazz critics of the time what the player was doing and how "good" he was at it. All you got was the song—dispassionately articulated with lots of spaces—swinging to be sure, but played mid-tempo and mid-range, shot through with melodic and rhythmic nuance that defied notation or interpretation. Baker's album, then, was a totally other form of expression for its time. Its only contemporary aesthetic analogy was in the cool economy and intellectual athletics of long-board surfing—another lost art of living in real time that may be coming back."
All the while, the minions and mavens of the "serious jazz world" stood on the sidelines, exasperated on the one hand that Baker refused to do something "historical," like Miles, that they could write about and teach in their college courses, and annoyed on the other hand that he continued to play so beautifully, that he refused to quit and be the bum they wished he was. "It really pissed them off, " Lowell George told me once, "that they couldn't learn anything from Chet's playing, not anything they could teach. All they could learn was that he could do it, and they couldn't. It was all about thinking and breathing in real time, and they couldn't grasp that. It had too much to do with life, with how you live in time."