The album was originally conceived after Richard Thompson, along with many other artists, was asked by Playboy magazine to nominate his choice of the best songs of the last 1000 years. He took them exactly at their word and served up a list that included the oldest-known English-language songs, a medieval Italian dance tune and various other folk songs alongside slightly more contemporary fare. The list was never published by Playboy; it was subsequently released into CD format. The songs comprising the track list cover a roughly thousand-year period, 1068–2001, starting with "Sumer Is Icumen In". The most recent song included on the album is Britney Spears' hit "Oops!... I Did It Again".