Some of Richmond's earliest publication work was for the comic book Married... with Children for NOW Comics, and the mini-series The Coneheads for Marvel Comics in the early 1990s. Specializing in caricature, he began doing editorial illustrations for magazines, art for advertising and CD-ROM graphics in 1992. In the late 1990s he had a brief stint at Cracked magazine before beginning to work for Mad magazine in 2000. Now a major contributor to Mad, Richmond's caricatures and cartoons illustrate many of Mad's trademark movie and TV parodies. He was the first illustrator in the modern (non-comic book) era to do his TV and film parodies in full color, coinciding with Mad's switch to a color format in 2001. In addition to MAD, Richmond continues to do freelance illustration for a variety of publications and advertising clients.
