Chet Baker Sings is the first album where Chet Baker, in addition to playing the trumpet, sings. It's like a duet with himself, with two modes of expression that are so alike. Chet Baker sings like he plays his instrument, with the nonchalance of a California dandy, all soft cotton and effortless precision, always on key, at the edge of a yawn that feels oddly soothing. No man had ever sung jazz like this before Chet Baker. But plenty of women had. The success of Chet Baker as a singer may lie in this ambivalence between his brooding, handsome looks and his almost androgynous voice. Backed by a small, ethereal orchestra and working through a repertoire of covers, Chet Baker here invented the ultimate resting space for modern jazz. Special mention goes to his version of "My Funny Valentine," a melancholic coo that has entered the pantheon of classics.