The woman on the cover of the 1963 album Organ Moods was possibly used as a reference by Clowes for the cover of the Misfit Lit exhibition catalogue (1991). It’s a generic pose, with some differences, so I wouldn’t say it’s a 100% certainty but when I saw the record my mind immediately felt like I’d seen it in Clowes’ work somewhere before.
I thought I’d made a new discovery with this, I was very pleased with myself, but with a little more searching I found people had already made the connection three years earlier, with some discussion coming up after cartoonist Jim Blanchard posted the cover on Flickr:
For a little more about this album, including a sample track, see here:
A collection of wonderful title panels from female-led comics of the 1940s. (Click each image for source info & credits.)