I saw Ronnie Hawkins play near my hometown, Port Dover, Ontario, and I saw him play there on New Year's Eve and the following spring I booked myself to be his opening act on maybe five shows, and he hired me after the first night.

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By 1965 with two singles under their belt recorded as the Canadian Squires they met the legendary blues harmonicist and vocalist Sonny Boy Williamson and planned a collaboration with him as soon as he returned to Chicago. "Originally [guitarist/vocalist Jason] Isbell tried to tell the story of Rick Danko Richard Manuel and The Band's demise but found the scope of the concept too difficult to actually do justice to their story and instead shifted the concept to a telling of life of a musician through the eyes and actions of Danko and Manuel. The group had been planning to leave Hawkins and strike out together as a band without a frontman as a team of equal members.