Mad #299

Mad #299 (December 1990) delivers a wonderfully cheeky cover by Mort Drucker: Bart Simpson's enormous head dominates the pink background, wearing that signature smug grin, while a tiny Alfred E. Neuman rides a lawn mower right across the top of Bart's spiky hair, sending yellow spikes flying. Inside, Mad takes aim at two of 1990's biggest cultural phenomena — The Simpsons and Total Recall — with work from writer Don Edwing and artist/inker Bob Clarke. It's a snapshot of a genuinely fun moment when two of pop culture's most mischievous faces squared off on the same cover.