The story of the intersection of the Band and Bob Dylan is an interesting one. It is told in some detail on the documentary DVD Down in the Flood (Sexy Intellectual 571).
It all more or less starts with semi-obscure rockabilly artist Ronnie Hawkins and his migration to Canada for a long series of gigs. His backup band, the Hawks, includes drummer Levon Helm and, eventually, is replenished with the Canadian musicians who were to be known as the Band. Meanwhile Bob Dylan makes a decision to go electric and eventually hires the Band (sans Helm) for a grueling European-Australian tour that was exhausting and not always well-received (there were those who thought his electrification was a sellout).
The DVD covers all that with good documentary footage, interviews, etc., and then goes on to tell of the important aftermath, where Dylan and the Band settle in Woodstock, the Band install themselves in the "Big Pink" basement studio and go on to do an experimental series of roots-and-beyond music tapes with Dylan and, eventually, to begin working on their own music.
There is a kind of cultural break that occurs with Dylan as it did with the Dead after Altamont--and others as well. There is a reaction, a satiation with throbbing rock electricity, with the excesses of psychedelic-Dionysian communal ecstasy and a look backwards to more acoustic fundamentals and down-to-earth whole-grain-brain alternatives. The DVD covers that break for Dylan and the Band, as well as the creative aftermath.
In a DVD that runs nearly two hours we go away with a nice encapsulation of the scene as Dylan and the Band experienced and shaped it. It's an important piece of rock music history. They do a good job with it. A must for Dylan/Band fans. Interesting even if you are not that.