Richard Thompson: 1000 Years of Popular Music(2006)

Richard Thompson: 1000 Years of Popular Music is a compilation album born from an unconventional challenge. When Playboy magazine asked Thompson to nominate the best songs of the last millennium, he took the assignment literally. The result spans roughly a thousand years of music, from the medieval English round "Sumer Is Icumen In" (1068) through Britney Spears' "Oops!... I Did It Again" (2001). Thompson's eclectic selection weaves together the oldest-known English-language songs, medieval Italian dance tunes, traditional folk music, and modern pop hits into a single journey through popular music history. Though Playboy never published the original list, it eventually emerged as this surprising CD—a testament to how music has evolved and endured across centuries.