[17][18][19] When Robertson was 14, he worked two brief summer jobs in the travelling carnival circuit, first for a few days in a suburb of Toronto, and later as an assistant at a freak show for three weeks during the Canadian National Exhibition.

At a Suedes show on October 5, 1959, when they played CHUM Radio's Hif Fi Club on Toronto's Merton Street, Ronnie Hawkins first became aware of them and was impressed enough to join them for a few numbers.

In early 1964, the group approached agent Harold Kudlets about representing them, which he agreed to do, booking them a year's worth of shows in the same circuits as they had been in before with Ronnie Hawkins.

Originally dubbed The Levon Helm Sextet, the group included all of the future members of the Band, plus Jerry Penfound on saxophone and Bob Bruno on vocals.

[30] Kudlets kept the group busy performing throughout 1964 and into 1965, finally booking them into two lengthy summer engagements at the popular nightclub Tony Mart's in Somers Point, New Jersey, at the Shore.

[35]: 95 Toward the end of Levon and the Hawks' second engagement at Tony Mart's in New Jersey, in August 1965, Robertson received a call from Albert Grossman Management requesting a meeting with singer Bob Dylan.

Drummer Sandy Konikoff left after the Pacific Northwest dates in March,[14]: 74  and Mickey Jones replaced him, staying with the group for the remainder of the tour.

[46] On July 29, 1966, Dylan sustained an injured neck from a motorcycle accident, and retreated to a quiet domestic life with his new wife and child in upstate New York.

[28] In time, word about these sessions began to circulate, and in 1968, Rolling Stone magazine co-founder Jann Wenner brought attention to these tracks in an article entitled "Dylan's Basement Tape Should Be Released".

He sang lead vocal on the track "To Kingdom Come"; he did not sing on another Band song released to the public until "Knockin' Lost John" on 1977's Islands.

[citation needed] In early 1969, the Band rented a home from Sammy Davis Jr. in Hollywood Hills, and converted the pool house behind it into a studio to recreate the "clubhouse" atmosphere that they had previously enjoyed at Big Pink.

[56] "Whispering Pines", co-written by Richard Manuel, was released as a single in France in 1970,[65] and was later the title of a 2009 book about Canadian contributions to the Americana music genre by Jason Schneider.

[79] Dylan and the Band played a number of tracks from the controversial 1965–1966 World Tour, this time to wildly enthusiastic response from the audience where there had been mixed reaction and boos nine years previously.

[60]: 26 Following the 1974 reunion tour with Bob Dylan, rock manager Elliot Roberts booked the Band with the recently reunited Crosby, Stills, Nash, and Young.

The main house on the property had originally been built by Lost Horizon (1937) actress Margo Albert,[81] and the ranch had been the filming and stabling site for the Mister Ed television show in the 1960s.

[14]: 298 [21]: 311–13 Shangri-La Studios proved to be a return to a clubhouse atmosphere that the Band had enjoyed previously at Big Pink, and in the spring of 1975, the group began work on Northern Lights – Southern Cross, their first release of original material in four years.

[59] The members of the Band were splintering off to work on other projects, with Levon Helm building a studio in Woodstock and Rick Danko having been contracted to Arista Records as a solo artist.

The group took a 30-minute break, during which several Bay Area poets, including Lawrence Ferlinghetti,[94] Diane di Prima,[95] and Michael McClure[96] performed readings of their poems.

[111] In the mid-1970s, Robertson connected with singer Neil Diamond, and the two began collaborating on a concept album about the life and struggles of a Tin Pan Alley songwriter.

[118] Also in 1980, Warner Bros released a soundtrack album for Carny, which is co-credited to Robertson and composer Alex North, who wrote the orchestral score for the film.

[121] Robertson also worked with Scorsese on selecting the film's opening theme music, choosing the intermezzo from Cavalleria Rusticana by Italian opera composer Pietro Mascagni.

Robertson worked on Scorsese's films Casino and Gangs of New York, and he provided music supervision for Shutter Island, The Wolf of Wall Street, and Silence.

[138] Robertson co-produced the track "The Best of Everything", which was originally intended for the film The King of Comedy but instead was included on the Tom Petty and the Heartbreakers album Southern Accents.

[citation needed] Rolling Stone gave the album 4 out of 5 stars,[160] and Robertson received a Juno Award for Best Music of Aboriginal Canada Recording.

It arose from impromptu demo sessions in Los Angeles with Eric Clapton[161] and features him, Steve Winwood, Trent Reznor, Tom Morello, Robert Randolph, Rocco Deluca, Angela McCluskey, and Taylor Goldsmith of Dawes.

It features Van Morrison joining Robertson as dueling hitmen on the track "I Hear You Paint Houses", as well as other allusions to the world of Scorsese's films.

On February 9, 2002, Robertson performed "Stomp Dance (Unity)" as part of the opening ceremony of the 2002 Winter Olympic Games in Salt Lake City, Utah.

[168] Robertson married his girlfriend of four years, Canadian entrepreneur, restaurateur, and Top Chef Canada judge Janet Zuccarini, on March 12, 2023, which was shared on her Instagram account.

[173][174] In May 2024, Robertson's three adult children sued his wife Janet Zuccarini, with claims of elder abuse and that she "took advantage of the musician’s declining health to have him sign documents that would favor her in the event of his death.

"[175] In October 2024, another tribute concert with Scorsese's involvement was held at the Kia Forum, which featured Bob Weir, Eric Clapton, Mavis Staples among others.