
Don't know if this is appropriate, as it's not a very old ad, but I thought I'd give it a whirl for its strangeness.
This button was a promotional piece about 1-3/4" in diameter, given out by shoe stores on the purchase of a pair of Keds, one of the sponsors of the daily kids' show "Fireman Frank" broadcast by KRON-TV in San Francisco during the mid-50s. Fireman Frank was George Lemont, a hip SF deejay who stepped into the role after the original Fireman, a roly-poly avuncular gent more in the style of a kids' TV host, dropped dead. Lemont's humor appealed as much to adults as well as kids; you could hear the studio crew guffawing off-camera at things that went over our heads. Between cartoons, Lemont brought out his cast of puppets, including robot Dynamo Dudley, the beret-wearing, bop-talking Scat the Cat and best of all, Karl the Karrot. Karl, as you can see, was a sort of proto-beatnik, literally a carrot with a pair of shades. His dialog consisted entirely of "blubble-lubble-lubble" while he thrashed about, chlorophyl topknot flailing. At home, we were all in convulsions on the floor.

A 1905 ad for Coca-Cola, which we need hardly remind you is a registered trademark of the Coca-Cola Company. Credit: NewspaperArchive.com

"Funniest show in the world - the huge pantomimic musical comedy. An Aerial Honeymoon invented and patented by John F. Byrne. A compartment for two. Passengers making it lively for the old bridegroom on his wedding trip." The boisterous comedy "An Aerial Honeymoon," which began its run in 1914, was produced by the pantomime brothers John, James, Matthew and Andrew Byrne. Color lithograph. View full image.

"Chas. E. Blaney's Big Extravaganza Success." This is a lithograph advertising the theatrical comedy "A Female Drummer," c. 1898. View full image.

A Coca-Cola chromolithograph from the 1890s. View full size. Now available as a Juniper Gallery Fine-Art Print in three delicious and refreshing sizes. Coca-Cola is a registered trademark of the Coca-Cola Company.

A very early use of Coca-Cola's now-familiar Spencerian script logo (at least the earliest example we could find in a newspaper archive of more than 64 million pages) was in this April 15, 1894, ad for the Douglas, Thomas & Davison soda fountain in Atlanta, birthplace of Coke and home of the new Coca-Cola museum. [Credit: NewspaperArchive.com]

An advertisement for Cascarets laxatives that ran in the Feb. 18, 1919, Daily Review of Decatur, Illinois. View full image