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The project is a satire of high-fashion snobbery and "lifestyle" consumerism, where the two producers adopt the personas of Nathaniel Merriweather and Chest Rockwell. The Core Concept

The album is celebrated for its eclectic mix of hip-hop, trip-hop, and alt-rock guests:

The group's name and concept come from "The Prettiest Week of My Life," an episode of the 1990s sitcom Get a Life . In the episode, Chris Elliott's character enrolls in a shady modeling school located behind a carpet warehouse to become a male model.