Clueless
It's 1995 and the impossibly rich kids of Beverly Hills are playing matchmaker, wearing Dr. Seuss hats, and navigating teenage life in Amy Heckerling's Clueless! Kevin and Mike tackle the role skateboard kid Travis Birkenstock (played by Breckin Meyer) plays in the film and how that maps to the experience of being "a skateboard kid" in high school. Also discussed: Jane Austen, the stupid late 90s swing revival, whether or not Wallace Shawn patronizes Hardees, and how much they both like this movie.
Episode here: Gleaming the Tube - Clueless