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This episode of A Productive Conversation features Chris Dalla Riva, a musician, data analyst, and Senior Product Manager at Audiomack who bridges the gap between creativity and analytics. Chris joins me to discuss his book Uncharted Territory: What Numbers Tell Us About the Biggest Hit Songs and Ourselves.As part of his research, Chris listened to every Billboard Hot 100 number-one song—nearly 1,200 of them—tracking trends, rating songs, and discovering how randomness, technology, and taste shape what becomes a hit. We explore the intersection of numbers and nuance, how data can deepen our understanding of art, and what the patterns of pop music reveal about us.Six Discussion PointsThe origin of Chris’s experiment to listen to every Billboard number-one hitWhy Bob Dylan never topped the Hot 100—and what that says about luck and timingHow data, subjectivity, and quality intertwine when rating songsThe cyclical nature of musical trends, from movies to TikTokThe uneasy relationship between music and technology—