Smilin' Jack, Sept. 21 1940, Joy and Mr. Irresistable.

The first thing that struck me comparing this with the daily, "Smilin' Jack Nov. 20, 1959, Second Wife", in this gallery is how much more distinctive and interesting the style is here compared to the 1959 piece. Joy actually became Jack's first wife. Since there is no comprehensive history of the strip that I could find, I have to draw from synopses of reprint books. Joy had a complicated run on the strip. I presume she must have died at some point since Jack got another wife and divorce just wasn't done in the comics back then. The guy she's talking to, Downwind supposedly had a face that, "drove women wild with passion." He was always drawn at this angle. It's hard to see how the pudgy cheek we see could be part of such a face. Mad Magazine had him with money clenched in his teeth. That might do it.