The Guess Who are a Canadian rock band from Winnipeg, Manitoba. Produced by Jack Richardson, C.M., the Guess Who were major stars in their homeland and found international success in the late 1960s with several hit singles, including "American Woman", "These Eyes" and "Share the Land". The Guess Who also spawned the successful group Bachman–Turner Overdrive, when founding member Randy Bachman departed the band.

On August 8, 1999, Cummings, Bachman, Peterson and Kale reunited once again, after responding to a personal request from the Premier of Manitoba, to appear at the closing ceremonies of the Pan American Games at Winnipeg Stadium. This led to a cross-Canada and US tour for the band beginning in 2000, although health problems precluded Kale's involvement. Nevertheless, he received a share of the band's earnings, and replacement Bill Wallace was paid out of other members' shares. A live album and DVD release followed the tour. Both the tour and the subsequent live releases were warmly received by fans and critics.

During the 2000 concert in Winnipeg it began to rain, then thunder, then lightning. Through the rain Cummings kept singing (while the band crew tried to cover things in plastic), at one point Cummings acknowledging that if the audience didn't leave he wouldn't either, and he didn't until the lightning started to strike. It was a temporary pause, though, and the concert continued a short time later.

In 2001, the band received honorary doctorates at Brandon University in Brandon, Manitoba. For lead vocalist Cummings, it was a privilege to receive the doctorate, since he did not graduate from high school. That same year the group was inducted into Canada's Walk of Fame.