Harry Hershfield - Desperate Desmond Drawing - Circa 1912

Sweet!

Question: How did people obtain drawings like this back then?  Were there actual fan letters that artists replied back with drawings?

Marcus, absolutely.  I have many specialty drawings like this, and sometimes the cartoonists would do a drawing on the back of the recipient's letter or postcard.  One famous collection was put together by Gladys Clements, who wrote to cartoonists and illustrators for decades, amassing an incredible collection.  I have a binder with photocopies of all the pieces fromt he collection.