The Guess Who were enjoying a resurgence in their popularity around the time of the live recording in Winnipeg on November 30, 1999. The concert was part of their "Running Back Thru Canada" tour, which celebrated their legacy as one of Canada’s most prominent rock bands. Prior to this recording, they had released "Playlist: The Very Best of The Guess Who" in 2001, a compilation that highlighted their earlier hits, including classics like "American Woman" and "These Eyes". This live performance showcased not only their enduring appeal but also the band's ability to connect with their roots in Winnipeg, where they formed. Notably, the concert served as a nostalgic nod to their extensive catalog, as they emerged from a prominent era in the late 1960s and early 1970s, proving their relevance in the rock scene well into the late 1990s and beyond.