JMW Auction Gallery had a sketchbook from Woody Gelman's daughter's estate offered recently, which seems like it contained a lot of very early work, some pre-Topps (and further, some post-Fleischer/Famous Studios):
This first batch dates to 1931-35. Cicero, anyone?
Three years later when Woody was attending college in New York City (City University of New York, Cooper Union and The Pratt Institute were his schools), he came up with these next two:
Woody's inimitable later ALL CAPS handwriting is featured at the top of these pages, juxtaposed with his very neat contemporary writing below his drawings, which had evolved from four years earlier at the time he drew this couple. From the looks of things, they are going to end up back at the dorm!
Holiday themed pipe dreams:
Here's some slightly later promotional work, I suspect accomplished as a freelancer:
Within two years he would be off to Fleischer Studios, eventually working on cartoons directed by future Topps Art Director Ben Solomon. But there was other work to be done. This looks like a commissioned book cover, possibly inspired by the earlier playing card illustrations but I'm not sure of the year here. Actually I'm not even sure it's for a book. Woody seemed to be quite taken with the Tales of the Arabian Nights.
I'll leave off with a bit of a later family portrait, in pencil, and from 1956 by which time Woody was well integrated at Topps. His handwriting had gone off the rails by then:
Richie was (and is) Richard Gelman, who ran the Card Collectors Company for a good length of time after Woody's passing and also did the hobby a huge solid in the late 80's by reissuing the American Card Catalog. His daughter Barbara does not look to be present. She was an author of sorts and did some brief work for Topps in the 60's.