A couple of years ago I bought a small stack of drawings that I soon later learned were the work of Bill Anthony, a mid 20th century artist/illustrator from Virginia, examples of whose work (somewhat more risque than this one, and also more absurd!) were presented in Josh Lowenfels booth at the 2019 Outsider Art Fair. (Blurb from artsy.net below.) I sold a number of them then and sat on the rest, but on this week when I didn't get out hunting, I pulled them back out and decided to list this and two others. Women in short skirts and very high heels were clearly his fixation, but the equal attention paid to faces and outfits and gestures and hairstyles I think makes them more interesting- perhaps partially a means of veiling or offsetting the former, but more so it seems to me central to the dynamic. 

10 1/4" X 8",  ink on card, good condition with minor corner bumps. 

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6 Inspiring Outsider Artists You Should Know, Scott Indrisek, Jan 18, 2019:

Bill Anthony, Joshua Lowenfels Works of Art

“He’s an up-skirt guy,” joked the gallery’s Kevin Duffy, reflecting on a series of ink drawings from the 1930s by Bill Anthony. Categorized as a series of portraits of “Fetish Chicks,” the works depict various anonymous women caught in the act of retrieving money from the floor. Sure, there’s something disturbing and borderline stalkerish about such a niche fixation, but Anthony’s fine draftsmanship adds a gentle touch to what might otherwise be plain creepy. There isn’t much known about the Virginia-born artist’s personal life. Gallery owner Joshua Lowenfels posits that he worked at a television station, and identified as a “self-proclaimed illustrator” with “a certain fetish for women dropping something in a tight spot.”