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 millennium in anticipation of the year 2000.

In an act of malicious compliance, Thompson followed these instructions exactly as they were worded, and produced a list which did span 1000 years of music, including the oldest-known English-language songs, a medieval Italian dance tune, and various other folk songs, alongside slightly more contemporary fare.

[1] 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!...

This was recorded in 2005 during a different tour, has a slightly different track listing and features Debra Dobkin replacing Michael Jerome on percussion and vocals.