Robertson was born Jaime Royal Robertson on July 5, 1943. He was an only child. His mother was Rose Marie Chrysler, a Cayuga and Mohawk woman who was raised on the Six Nations Reserve southwest of Toronto, Ontario. Chrysler lived with an aunt in the Cabbagetown neighborhood, and worked at a jewelry plating factory.

In late 1967, Dylan left to record his next album, John Wesley Harding (1967). After recording the basic tracks, Dylan asked Robertson and Garth Hudson about playing on the album to fill out the sound. However, when Robertson heard the tracks, he liked the starkness of the sound and recommended that Dylan leave the songs as they were. Dylan worked with the members of the Hawks once again when they appeared as his backup band at two Woody Guthrie memorial concerts at Carnegie Hall in New York City in January 1968. Three of these performances were later released by Columbia Records on the LP A Tribute to Woody Guthrie, Vol. 1 (1972).  Over the course of the "Basement Tapes" period, the group had developed a sound of their own, and Grossman went to Los Angeles to shop the group to a major label, securing a contract with Capitol Records. The group went to New York to begin recording songs with music producer John Simon. Capitol brought the group to Los Angeles to finish the album. The resulting album, Music From Big Pink, was released in August 1968.  Robertson wrote four of the songs on Music From Big Pink, including "The Weight", "Chest Fever", "Caledonia Mission," and "To Kingdom Come". Robertson is listed in the songwriting credits as "J.R. Robertson". Robertson sang lead vocal on the track "To Kingdom Come"; he would not sing on another Band song released to the public until "Knockin' Lost John" on 1977's Islands. Two of Robertson's compositions for the album, "The Weight" and "Chest Fever", would become important touchstones in the group's career. "The Weight" was influenced by the films of director Luis Bunuel, in particular Nazarin (1959) and Viridiana (1961), and reflects the recurring theme in Bunuel's films about the impossibility of sainthood. The song portrays an individual who attempts to take a saintly pilgrimage, and becomes mired down with requests from other people to do favors for them along the way. The mention of "Nazareth" at the beginning of the song refers to Nazareth, Pennsylvania, where the C. F. Martin & Company guitar manufacturer is located; it was inspired by Robertson seeing the word "Nazareth" in the hole of his Martin guitar. Although "The Weight" reached #21 on the British radio charts, it did not fare as well on the American charts, initially stalling at #63.  However, the song gained traction due to more successful covers by Jackie DeShannon (US #55, 1968), Aretha Franklin (US #19, 1969), and The Supremes with The Temptations (US #46, 1969), as well as to the song's inclusion in the movie Easy Rider (1969), which became a runaway success. "The Weight" has since become The Band's best known song. It has been covered by many artists, appeared in dozens of films and documentaries, and has become a staple in American rock music.  When Music from Big Pink was released in 1968, The Band initially avoided media attention, and discouraged Capitol Records from promotional efforts. They also did not immediately pursue touring to support the album, and declined to be interviewed for a year. The resulting mystery surrounding the group led to speculation in the underground press. Music from Big Pink received excellent reviews, and the album influenced many well-known musicians of the period.

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