“This is shocking news,” Dylan said in a statement provided to Billboard. “Robbie was a lifelong friend. His passing leaves a vacancy in the world.”
The two legends share a long history. Robertson, whom Dylan famously called a “mathematical guitar genius,” played guitar with Dylan starting in the mid-1960s, after Dylan became aware of Levon and the Hawks, an early iteration of what became The Band. As Dylan notoriously switched from acoustic to electric, their reception was hardly positive. As Robertson recalled to Mojo in 2017, “When The Hawks hooked up with Dylan, he found this explosive, dynamic thing. Because of his intensity, it raised everything up and we didn’t come down enough and people were saying this music is so loud we can’t hear the words. Part of that was he wanted that raging spirit on these songs. We got booed all over North America, Australia, Europe, and people were saying this isn’t working and we kept on and Bob didn’t budge.”
The Hawks backed Dylan for several months, with their efforts captured on 1998’s The Bootleg Series, Vol. 4: Bob Dylan Live 1966: The ‘Royal Albert Hall’ Concert.
Their relationship was exploratory and revelatory, especially in the early days. “The obvious thing we learned – that everybody learned – was there was a new way of songwriting. There was a much more colorful, descriptive, humorous, outrageous thrill ride of wordplay,” Robertson told Mojo. “We hadn’t seen this before – this was breaking some big rules. I remember saying to Bob one time, ‘Maybe there’s too many verses in this’ [Laughs], and he said, ‘There probably are, but that’s what I was thinking about when I wrote it.’ His spirit was on fire, and he was knocking down the boundaries that had been built up around music. It excited me to be part of this revolution.”
Robertson also played on Dylan’s legendary 1966 album Blonde on Blonde. Dylan and The Band famously recorded in 1967 at Big Pink, the house several members of The Band rented in West Saugerties, New York. The complete recordings from those sessions were released in the voluminous 2014 set The Bootleg Series Vol. 11: The Basement Tapes Complete.
Robertson and Dylan continued to collaborate for decades, including The Band covering Dylan’s “When I Paint My Masterpiece” on 1971’s Cahoots album and touring together in 1974, as well as recording Dylan’s No. 1 studio album Planet Waves together.
For the very successful 1974 tour, the audience finally realized Dylan and The Band were right all those years ago, Robertson told Mojo: “We do a tour, the  Dylan/Band tour, we play the same way [as we did in 1966], same intensity and everybody says, ‘Wow, that was amazing.’ The world came around – we didn’t change a note.”
Dylan also was one of a number of legendary musicians joining The Band for The Last Waltz concert, taped on Thanksgiving Day, 1976. The show concludes with Dylan’s “We Shall Be Released.”