Here is a sketch of folk singer Kirk Kelly, the model for Smirk Smiley. Kirk performed frequently at Lach's Anti hoot, and issued several records on independent labels. Although a 2004 interview quotes Kelly discussing songs to appear on his "next album" (including a song about patriot Nathan Hale), as of 2008 no recording appears to have materialized. Kelly continues, however, to make appearances where he both sings and speaks out for workers rights.
Here is a clip of Kirk performing live, year unknown: https://www.youtube.com/watch?v=i4GUku1p8u8