Recently I've been doing some non-Gopher related research on one of the first newspaper cartoonist Charles L. Bartholomew. Better known as Bart, he drew for the Minneapolis Journal. Most of his drawings satirized politics of the early 1900s. However some are about Minnesota football and that's awesome.
From the Little Brown Jug game comes one of the earliest newspaper cartoons.
/cdn0.vox-cdn.com/uploads/chorus_asset/file/6506297/cartoon.0.jpg)