What really sold me on this pair was the profile expression and posture of the woman, with hand on her hip, though this funny little gangster-looking man, I'd guess with a cigar in his mouth, is pretty fun, too. I've learned from a helpful customer that they are characters Jiggs and Maggie, from "Bringing Up Father" an American comic strip created by cartoonist George McManus, which launched in 1913. (More below). These iterations were certainly drawn long ago, on the back of a poster advertising a musical comedy with Blossom in the title somewhere, performed by St. Paul's Dramatic Society at the Brown Township School, which I think may be in Indiana. Anyway, quite a pair! 

Jiggs drawing measures 4 7/8" x 2". Maggie 5 3/16" x 2 5/8". Light staining/foxing and browning & bleeding of what I would guess was once black ink, which I think is part of what makes them good. Sold as a pair.

From Wikipedia: The character of Jiggs was an Irishman and former Hod carrier (assistant to bricklayers) who came into wealth in the United States by winning a million dollars in a sweepstakes. Now nouveau-riche he still longs to revert to his former working class habits and lifestyle. His constant attempts to sneak out with his old gang of boisterous, rough-edged pals, eat corned beef and cabbage and hang out at the local tavern were often thwarted by his formidable, social-climbing (and rolling-pin wielding) wife Maggie.