Jon Stewart

One of Jon Stewart's higher-profile acting roles came in the 1999 Adam Sandler comedy Big Daddy, the highest-grossing of Sandler's films to date. Here they are in Angelo Torres' artwork for "Big Bladder," one of three mini-parodies written by Desmond Devlin as part of the nine-page article "Foley and Walsh Go To The Movies." It originally ran in black-and-white in MAD #387 (November '99) and was given the rainbow treatment for the second issue of the MAD Classics series.

Sam Sisco caricatured Stewart (and, coincidentally, Adam Sandler) for the two-page article "What Celebrities Laugh At." The only MAD byline for writer Bob Wieder, it originally ran in MAD #457 (September '05).

Writer Desmond Devlin had two opportunities to zing Jon Stewart and The Daily Show within his regular series "MAD Deconstructs TV Talk Show." Here's the first, illustrated by Drew Friedman and specifically centering on The Daily Show at roughly the midway point of Stewart's 16-year run as host. Originally appearing in MAD #467 (July '06).

In addition to The Daily Show, Jon Stewart served as executive producer of The Colbert Report during its decade of airings on Comedy Central. Sam Viviano caricatured Stewart and protege-of-sorts Stephen Colbert in the edition of Desmond Devlin's "MAD Deconstructs TV Talk Show" series that focused specifically on The Colbert Report. It originally ran in MAD #484 (December '07). (Footnote: Stewart is also an executive producer and occasional guest commentator on CBS' The Late Show With Stephen Colbert.)

Artist Tom Richmond has had a couple of opportunities to caricature Jon Stewart (usually in tandem with Stephen Colbert). Along with "MAD Exposes Who's Thinking What At The Obama Inauguration" (MAD #498, February '09), Richmond had the two political jesters harmonizing on a parody of "Follow The Yellow Brick Road" on the third page of the ambitious Desmond Devlin-penned parody "The Wizard of O." Originally running in MAD #505 (October '10).