Artist Tom Richmond is a native of Wisconsin. He crossed the border during his college years to work as a caricature artist at Six Flags Great America. He claims his work sucked in comparison to others and his goal became "not to suck." I think Richmond is underestimating his ability back then, but either way, his ability now is undeniable.
Richmond worked at a variety of jobs involving caricatures. He evetually worked for Cracked, although his dream was to work for Mad. Eventually, he did land his dream job at Mad. He also does commissions, which you can purchase through his site or at comic cons throughout the year.
Richmond is very approachable at comic cons. In fact, rarely is someone so accomplished, so under the radar at such places. This man's work appeared in Mad! That magazine brought tears of laughter to generations. It inspired many kids (including me) to attempt to reproduce the caricatures. I first saw and fell in love with caricatures, although I never developed that talent. I could copy their work free hand pretty well, but I could not create original caricatures.
Richmond's work is amazing, whether it is for Mad or other creations. You can see a lot of his awesome work on and get more info, including his appearance schedule at TomRichmond.com. You can also follow Tom Richmond on twitter.
Tom Richmond and me in Chicago, IL-March 2016.