The hosts dive into 1999’s cultural landscape through an economic lens, selecting movies, songs, and wild cards that reflect broader financial and societal patterns. Wailin champions *The Insider* for its corporate whistleblower narrative and later chooses *House Hunters*, which she argues reshaped American real estate desires. Jeff highlights *Pokémon: Mewtwo Strikes Back* as a global export phenomenon and picks the Backstreet Boys’ 'I Want It That Way' to explore relational economics, before closing with Napster—a disruptive force that redefined music consumption. The discussion reveals how entertainment mirrored shifts in consumer behavior, gender dynamics in finance, and digital innovation, from viral horror marketing to failed dot-com ventures like Flooz.com. Each selection underscores the interplay between culture and economy, showing how 1999 laid groundwork for modern media and tech trends. In the end, Wailin’s cohesive, insightful lineup earns her a decisive victory.