Throwing out ideas in case it incites something with the others:
3. Not Winnie The Pooh, but a bear with a honey jar.
10. This one is driving me crazy; I was thinking 40's/50's cigarette ad (look at the gifts), then stewardess, then Oreo Cookie Tin (the commemorative ones). Got nothing. (Though I will say, the ads in the 50's and 60's, especially for things like cigarettes and air travel as SEXIST AF.)
11. Gondola from Venice, but is that a caricature of the Leaning Tower of Pisa? Is that an ad for Italia?
13. Already said, I thought it was William Lee Golden but now don't think so. It's not Leon Russell either.
15. No clue
18. I thought it was an extreme closeup of a character of some kind; that being the smile and nose of a dog maybe?
20. Smiling ear of corn.
22. Flame ball; the pixels could be a video game or just a low quality photo. Heart burn ad? Athlete's Foot?