These were usually found as a prize in a bubble gum or peanut vending machine in the 1950's - 1960's. This is a collection of 5 rings that appear the to be the same age and condition. One ring features a photo of Gene Autry, the Singing Cowboy. Three rings features a photo of Alfred E. Newman, the fictitious mascot and cover boy of the American humor magazine "Mad". And one features a photo of Frank Sinatra and the words "IT'S FRANK SINATRA'S WORLD WE JUST LIVE IN IT". My sister-in-law was an avid collector of so many things, jewelry was just one category. She knew everything about each and every one of her pieces but unfortunately she is no longer able to tell us. I'm not an expert - I just offered to help find new homes for her beloved pieces. This is a vintage piece and has evidence of wear that is appropriate for its age. Please examine all photos closely for condition.