For several years Thompson devised and toured his show "1000 Years of Popular Music". The inspiration for this came when "Playboy" asked Thompson (and many other music industry figures) in 1999 for their suggestions for the "top ten songs of the millennium". Guessing that "Playboy" expected most people's lists to start at around 1950, Thompson took the magazine at its word and presented a list of songs from the 11th century to the present day. Perhaps not surprisingly, "Playboy" did not use his list, but the exercise gave him the idea for a show which takes a chronological trip through popular music across the ages. Thompson acknowledges that this is an ambitious undertaking, partly because he reckons that he is technically unqualified to sing 98% of the material, and partly because of the sparse musical setting he restricts himself to: besides his acoustic guitar, he's backed by singer/pianist Judith Owen and percussionist/singer Debra Dobkin. A typical performance would start with a medieval round, progress via a Purcell aria, Victorian music hall and Hoagy Carmichael and end with Thompson's take on the Britney Spears hit "Oops!... I Did It Again".