Though Staples and Helm got on like childhood pals, the two were already both stars in their own right by the time they first met at the 1976 filming of ‘The Last Waltz’. Critics would go on to cite The Staple Singers’ collaboration with The Band on “The Weight” as a high point of the film, and Mavis and Levon would remain close friends in the decades to come, but it was unclear if the pair would ever get to sing together again after Helm was diagnosed with throat cancer in 1998. More than two dozen radiation treatments robbed him of his voice, and, as Helm told Fresh Air’s Terry Gross in a 2007 interview, “I had a period of time there for about two-and-a-half years or so where I had to whisper or write you a note to tell you what I wanted you to know.” But when Staples arrived in Woodstock for the Ramble, the ever-resilient Helm was in the midst of a genuine renaissance. The cancer was in remission, his voice had returned, and he’d won a pair of GRAMMY Awards for his two most recent solo albums (he’d take home his third less than a year later). On top of all that, Helm, much like Staples, was now more in demand than ever, sought out by a younger generation of artists who rightfully revered him not only as one of the greatest drummers of all time, but as a patron saint of the American musical canon.