Talent Manager and pop culture aficionado Desiree Middlebrook joins Andy to talk about the teen comedy "Clueless." Now 29, this movie remains a towering comedic classic. Why is this piece so good at poking fun without being a farce? How does it manage to allow for biting societal critique while effortlessly giving us real, layered characters? Heckerling repeats her prowess as a master of the "slice of life" introduced in 1982's "Fast Time at Ridgemont High."

Desiree, having been influenced into the casting/management world by "Clueless," directs a unique lens to view the casting decisions, and get under the hood of this killer ensemble, and why it is indeed a perfect group of players.

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