You ask a question here, you get answers…
- JEFF GRUBB: I think the characters come from the old Saturday Evening Post. They had a humor/cartoon page in the back, with these little guys in the title bar.
- LES DANIELS: I can offer a tentative tip on that cartoon. When I was a kid in the 1950s, my parents had a sub to the Saturday Evening Post, which interested me mostly for the cartoons they ran. I recognize the style of "You want it when?" from the Post of a half a century ago or more. I'm sure this artist was a regular there, but I can't remember his name. I realize this is a pretty slim lead…
- BEN HERNDON: Double check me, but I always had the impression these laughing characters were drawn/created by Stan and Jan Berenstain (of "Berenstain Bears" fame…)
- RUSS MAHERAS: I'm almost positive that cartoon illustration was drawn by Orlando Busino, and I'm also pretty sure it originally appeared on the cartoon page of the Saturday Evening Post.
- MIKE LYNCH: The "You want It When" guys are a question I've had too. I'm a magazine cartoonist, as well as an NCS member. I've always been interested in the magazine cartoonists. I've talked about that iconic image to a lot of the pros. The consensus is that it was drawn by Henry Syverson. There are some images here.
- GALEN FOTT: Looking on Usenet, someone wondered this back in 1993, and they were referred to some books by Alan Dundes, titled with variations on Urban Folklore from the Paperwork Empire. So maybe you could find the answer there.
- NATE BUTLER: I think it's from the Saturday Evening Post…from the top of that page (toward the back, as I dimly recall) that had all the jokes or gag panels or whatever. I think the "You Want It When?" wording got added later maybe. I don't remember the name of that cartoonist who always did those little big-nose characters on the top of that page of the Post, but I'm pretty sure this is where the mystery art came from originally.
- BRAD CASLOR: I'm not sure if this was the first use, but weren't the laughing cartoon guys the recurring mascot on the "Post Script" humour page of the Saturday Evening Post in the 1950s, possibly drawn by one of the regular Post cartoonists like John Gallagher?
- TIM (no last name): I absolutely don't know who drew it but the guys in the drawing are dead ringers for cartoon characters that were in the Saturday Evening Post when I was a kid (60s). In fact, I believe they were at the top of the page but I can't find an example anywhere yet (if I do I will send it). I think what you're talking about was created by ripping off these guys from the page and adding "you want it when" but that's just a theory.
- JOHNNY LEE ACHZIGER: This won't help much, but I remember back in the early 1960's (when Xerox machines still required a couple trays of wet chemicals to make copies) watching my Dad make copies of the same sort of cartoons like this at his office. There were a bunch of different ones, but they were in the same style. So even way back when, they were around.
- SCOTT SHAW!: That cartoon — or at least, the original version from which it was traced (over and over and over, etc.) — was drawn by magazine gag cartoonist Henry Syverson, who regularly did such silly drawings for Saturday Evening Post's page of cartoons. I think that the "You Want It When?" was added by someone else.
I think Scott and the others who've fingered Henry Syverson are right. The samples Mike Lynch pointed us to seem to confirm it. So for now, I'm willing to go with Syverson and what I'm wondering is if he or the Post ever marketed a poster or sign of the drawing or if its life in Xerox just began with someone blowing it up. For now, thanks to all who've sent in their thoughts.