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. The magazine intended the use of the term "millennium" to be hyperbole that emphasized the end of the 2nd millennium or songs within the collective memory of their readership at that time, probably expecting nothing earlier than the British Invasion at best. 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.[2] The list was never published by Playboy; it was subsequently released into CD format.[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!... I Did It Again".
The songs, arranged for play on a single guitar, are played by Thompson, vocalist Judith Owen, and percussionist Michael Jerome, when needed.
A DVD with the same name was released in 2006. 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.
"Marry, Ageyn Hic Hev Donne Yt" (Traditional, arranged by Thompson) – introduced as a "medieval tune from Brittany", but actually a medieval-style version of Britney Spears' "Oops!... I Did It Again"
Track listing of 2CD/DVD version
(Recorded at Bimbo's club, San Francisco, 2005)
"Sumer Is Icumen In" (trad., arr. by Thompson)
"King Henry" (trad., arr. by Thompson)
"So Ben Mi Ca Bon Tempo" (Orazio Vecchi, arr. by Thompson)