Kelly’s artistic screeds are devoid of irony, but as the invention of Colorado-based cartoonist Ward Sutton, Kelly the character — much like Stephen Colbert’s former Comedy Central bloviator — is composed almost entirely of irony. And that joke-within-a-joke makes all the difference.

...

Sutton is a true student of old newspaper comic strips and cartoons, so what emerged was a character whose persona embodied this “man out of time” approach — a cartoonist who is himself a caricature of a blind-to-his-own-buffoonery pundit, producing old-timey cartoons that ripple with parody.

A visual stroll through the Kelly collection is like a meta-history lesson in editorial cartooning before sardonic subtlety became fashionable. Kelly’s illustrations, reflecting wading-pool deep takes on the news, are larded with labels (“today’s no-good teens,” “today’s troop haters,” “benevolent America”) that skewer the worst practitioners of the art form. Kelly sees himself as a political “king of comedy,” but in truth, he is as deluded as Robert De Niro’s bad stand-up Rupert Pupkin in Martin Scorsese’s “The King of Comedy.” He would have been painfully mediocre at best in his own era; in our era, he is laughably hackneyed.

https://archive.is/nDvkY

Ben Garrison uses this style unironically, so at a glance it's hard to tell. https://knowyourmeme.com/memes/people/ben-garrison