While other artists find themselves drawing reinterpretations of their favorite comic book characters, Chris Schweizer draws caricatures of his favorite cartoonists, including ones that you could cut out as paper figurines. He also applies his character design skills to a number of pop culture phenomena, including a series of Harry Potter designs that are refreshingly distinct from the films (and take a few liberties with the books as well).
Schweizer is the creator of the Crogan Adventures books. Each book follows a member or two of the Crogan family in a different historical period--with Caribbean pirates, French legionnaires and American revolutionaries. Schweizer enjoys mixing history and fiction, but he also has a way with other people's characters, as his Harry Potter series proves. I would love to see a series of spinoff stories set in his version of the Wizarding World. In addition to these and his loving series of portraits of cartoonists, he has some really stellar pieces up on his blog, including the Muppet cast of Sesame Street reimagined as Star Wars Droids.