It's appropriate that his most famous vocal tune is "My Funny Valentine." In this Rodgers and Hart tune, we have a psychic match between performer and song. This is a song that spells out the imperfections of the lover ("is your figure less than greek, is your mouth a little weak, when you open it to speak are you smart"). Look at the title itself-my "funny" valentine; not that the lover is funny/humorous, but funny as inhow did this happenhow did I end up with someone like you. This is love as mystery, song as mystery, sung by a musician whose life was lived publicly, but who was a mystery. Yes, we know the biographical facts of Baker's life, but the inner life was shrouded in layers of romanticism and self-protection.
It's difficult to show the influence Baker had, as he didn't overtly inspire a generation of male singers. Most tenor-range jazz vocalists remained more beholden to older approaches. Jimmy Scott, Tony Bennett, Johnny Mathis, Mose Allison, Oscar Brown, Mark Murphy, Jackie Paris and Sammy Davis, Jr. were all much "hotter" singers.
But I contend that Chet Baker changed the "field" and in so doing influenced these singers. He brought the ethos of cool to a kind of climax by moving into territory that had once belonged only to female vocalists and opened up the emotional space to show vulnerability; a space that male singers had previously shied away from and which they were now more likely to inhabit.
Ironic that Chet Baker, who created such distance between himself and others was able to transmute this distance into a kind of intimacy that had rarely, if ever, been expressed in the pop-jazz male voice.
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