And now we go from hopeful to hopeless with the same artist. As much as James Taylor’s voice has communicated reassurance and comfort to me on a number of occasions, the man has released some of the most profoundly sad songs I know. “Another Grey Morning”, from 1977’s album JT (his Columbia Records debut and the first result of what was essentially a baseball-esque trade with Warner Brothers for Paul Simon), is proof of that.

“Another Grey Morning” is a character sketch of a woman who is in the throes of depression. She’s looking for something to take her out of her doldrums, and is leaning on the song’s narrator (presumably a romantic interest) for comfort. The narrator doesn’t know what the hell to do, and the final lyrics bring into stark view how profound these feelings of sadness are: “no more grey morning/I think I’d rather die.” For his part, James sings it with a sensitivity and a sadness that’s almost tangible.

As different as their upbringings may be (one born dirt-poor and blue-collar in West Virginia, the other born into upper middle class comfort and based out of Cape Cod), Bill Withers & James Taylor have always felt super similar to me. Their peak artistic and commercial periods were about the same time, much of their music is centered around their acoustic guitar playing, and they both are what one might consider “sensitive” and others might consider “depressed”, although Withers’ lyrics have a bit more of a harder edge than JT’s (I don’t see James writing something like “Who Is He And What Is He To You”, but I could be wrong). “Another Grey Morning” has some sonic similarities to “Ain’t No Sunshine” the same way that (and I just discovered this as I was thinking about what I was going to write here) “Lovely Day” has a more-than-passing resemblance to “Your Smiling Face”. It’s a shame the two never worked together. I guess it’s not too late as they’re both alive and seem relatively healthy, but Withers’ reluctance to come out of retirement pretty much leaves me resigned to that collaboration remaining a wish.