An artist at the school carnival draws a cartoon caricature of Lisa. When she sees it, Lisa is appalled with her appearance and develops an inferiority complex. Meanwhile, Homer wins a ride on the Duff Blimp. Noticing that Lisa is insecure about how she looks, he enters her in the Little Miss Springfield Pageant, selling his blimp ticket to come up with the $250 entry fee.

Lisa refuses to participate in the pageant. When Marge tells her that Homer sold his blimp ticket because he loves her, she finally agrees. Marge takes Lisa for a complete beauty makeover to help boost her confidence. The judges crown professional pageant participant Amber Dempsey as Little Miss Springfield, voting Lisa runner-up.

When Amber is struck by lightning, Lisa takes over the title and becomes spokesperson for Laramie Cigarettes. While riding the Laramie float in the Springfield parade, Lisa announces that smoking cigarettes is evil. Pageant officials strip Lisa of her crown. Relieved, Lisa thanks Homer for helping her see true beauty.