My favorite track of his (largely because it's the first one I ever heard) still is "Ain't No Sunshine" from his debut album, Just As I Am (1971). It's a deceptively simple song: a short phrase ("I know") that gets repeated a total of 26 times, bookended by a few short lines that (on the surface) are about longing for lost love.
As a little kid, I liked the track because it was easy to learn and remember. I also enjoyed the counting game that my mom would play with me, where she'd challenge me to count the 26 I know's.
But as I got older, I started to realize that "Ain't No Sunshine" isn't some torch song, where ol' Bill is pining away for his woman. It's a song about the vicious cycle of dependency.
Withers pretty much confirmed this in a 2004 interview with Carl Wiser of Songfacts.com.
"It's pretty obvious what it's about. I was watching a movie called Days Of Wine And Roses (1962) with Lee Remick and Jack Lemmon. They were both alcoholics who were alternately weak and strong. It's like going back for seconds on rat poison. Sometimes you miss things that weren't particularly good for you. It's just something that crossed my mind from watching that movie, and probably something else that happened in my life that I'm not aware of."
Musically, it's beautifully melancholy. But it also grooves like crazy. After all, he had 3/4 of Booker T. & The M.G.'s (minus Steve Cropper) + Stephen Stills backing him on the single.
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