This article looks at how "The Simpsons'" representations of aging, considered ageist and stereotypical by some, can be viewed as a positive look at the elderly that attempts to subvert the same stereotypes that it seemingly employs. The Baby Boom cohort is now seen as an attractive economic group, and as they continue their journey through the life cycle, they are drawing increased attention. A current scholarship exists that investigates the ways that the "aged" are seen, catered to, advertised at, seemingly marginalized, and represented in the larger context of the mass media. Relying primarily on the theoretical musings of Frederic Jameson and Linda Hutcheon, the article constructs a bridge that places "The Simpsons" squarely within a postmodern aesthetic and, using this rubric, shows how the inherent political nature of parodic irony can help to create an inversion of meaning.