The picture shows a view of all (8) Old Gum Ball Machine Prize ComicStripCharacter Charms in this lot. These are not dated but they were used as prizes in 1940s and 1950s machines. Some of these are from the Katzenjammer kids comicstrip. Included (in the order pictured) are the following characters:
CASPER INSPECTOR TOOTS INSPECTOR HANS MAGGIE MAMA JIGGS
To judge the sizes the first charm measures 1'' tall. These appear to be in excellent to mint condition as pictured. Two of them are missing the loop.