By 1959 he had met singer Ronnie Hawkins, who led a band called The Hawks after he had relocated to Canada. In 1960 Hawkins recorded two early Robertson songs, "Hey Boba Lu" and "Someone Like You" on his Mr. Dynamo LP. Robertson then took over lead guitar with The Hawks and toured often, before splitting from Hawkins in 1963.
After Robertson left The Hawks with Levon Helm, Richard Manuel, Rick Danko, and Garth Hudson, the quintet styled themselves as The Canadian Squires and Levon and the Hawks, but (after rejecting such tongue-in-cheek names as The Honkies and The Crackers) ultimately called themselves The Band.
Bob Dylan hired The Band for his famed, controversial tour of 1966, his first wide exposure as an electrified rock and roll performer rather than his earlier acoustic folk sound. Robertson's distinctive guitar sound was an important part of the music; Dylan famously praised him as "the only mathematical guitar genius I’ve ever run into who doesn’t offend my intestinal nervousness with his rearguard sound." Robbie appears as one of the guitarists on Dylan's album Blonde on Blonde.
From their first album, Music from Big Pink (1968), The Band was praised as one of rock music's preeminent groups. Rolling Stone magazine praised The Band and gave its music extensive coverage. Robertson sang only a few songs with The Band, but was the group's primary songwriter, and was in the later years of the Band often seen as the de facto bandleader.
In 1976, The Band broke up due to the stresses of sixteen years of touring. In the Martin Scorsese film The Last Waltz (1978) Robertson noted that he had been playing live rock and roll music almost since rock and roll began. Also, credited officially as the band's main songwriter, he was able to live off the song royalties, and no longer needed to tour. The Band reformed in 1983 without Robertson.
Robertson produced Neil Diamond's albums Beautiful Noise in 1976 and Love At The Greek (live) in 1977.
Between 1979 and 1980 Robertson co-starred with Gary Busey and Jodie Foster in Carny. He also co-wrote, produced, and composed source music for the film. Inspired by Carny soundtrack composer Alex North, with whom he worked, Robertson became one of the first rock 'n' rollers to seriously engage the medium of film. For Scorsese's Raging Bull, Robertson created background music and produced source music.
Between 1982 and 1986 Robertson managed to stay quite busy. For another Scorsese film, The King of Comedy (released in 1983), Robertson serves as music producer, assembling tunes by The Pretenders, Talking Heads, Ray Charles, Rickie Lee Jones and others. He also contributes with his first post-Band solo recording, "Between Trains." Additionally, he produced and played guitar on Van Morrison's song "Wonderful Remark". Robertson signed via A&R executive Gary Gersh for his debut solo album on Geffen Records. Robertson recorded with producer (and fellow Canadian) Daniel Lanois. He also scored Scorsese's The Color of Money (1986), working with Gil Evans, and co-wrote with Eric Clapton (It's In The Way That You Use It") and Willie Dixon.[clarification needed]
Robertson was enlisted as creative consultant for Hail! Hail! Rock 'n' Roll (1987), Taylor Hackford's film saluting Chuck Berry.
From 1987 onwards, Robertson released a series of four solo albums, his first was self titled followed by Storyville, Music for the Native Americans and Contact from the Underworld of Redboy. In 1990, he contributed to Japanese musician Ryuichi Sakamoto's album Beauty. Robertson's song "Broken Arrow", off the Robbie Robertson album, was covered by Rod Stewart on his album Vagabond Heart and became a hit single. "Broken Arrow" was also a part of the Grateful Dead's rotation of live songs 1993-95 (sung by bassist Phil Lesh), and later with Phil Lesh and Friends. The song "Somewhere Down the Crazy River", became Robertson's biggest solo hit, charting in the UK and Canada.
In 1994, Robertson returned to his roots, teaming with the Native American group the Red Road Ensemble for Music for The Native Americans, a collection of songs composed for a television documentary series.
Also in 1994, Robertson joined Garth Hudson and Rick Danko onstage to perform "The Weight" when The Band was inducted into the Rock and Roll Hall of Fame. Levon Helm, who had a falling-out with Robertson after The Band broke up, did not attend.
In 1995, in Rome, Robertson headlined an annual Labor Day concert festival with support acts Andrea Bocelli, Elvis Costello, and Radiohead. More than 300,000 fans attended the event.
In 1996, Executive soundtrack producer Robertson heard a demo of Change The World and sent it to Clapton as a suggestion for the soundtrack to Phenomenon, starring John Travolta. He then enlisted Babyface to produce the track. Change the World won 1997 Grammy Awards for Song of the Year and Record of the Year.
In 1997, Robertson received a prestigious Lifetime Achievement Award from the National Academy of Songwriters.
From 1997 to 2000, Robertson stayed busy with side projects and documentaries.
In 2000, music industry legends David Geffen and Mo Ostin convinced Robertson to join DreamWorks Records as Creative Executive. Robertson, who persuaded Grammy Award winner Nelly Furtado to sign with the company, is actively involved with film projects and developing new artist talent, including signings of A.i., Boomkat, Daniel DeBourg, eastmountainsouth, and singer-songwriter-pianist Dana Glover.
On 9 February 2002, Robertson performed "Stomp Dance (Unity)" as part of the Opening Ceremony of the 2002 Winter Olympic Games in Salt Lake City, Utah.
At the 2003 commencement ceremonies at Queen's University in Kingston, Ontario, Robertson delivered an address to the graduating class and was awarded an honorary degree by the university.
In 2006, he announced plans to write his autobiography.
In 2003, Robertson was inducted into Canada's Walk of Fame.
In 2006, Robertson recorded with Jerry Lee Lewis and Samuel Bidleman on "Last man standing" on track "Twilight". That same year, he received the Governor General's Award for Lifetime Artistic Achievement.
On July 28, 2007, at Eric Clapton's Crossroads Guitar Festival in Bridgeview, Illinois, Robertson made a rare appearance on stage and played briefly.
According to an article in the February 9, 2008 edition of the Winnipeg Sun, Robertson is said to be working with Eric Clapton on an album of new material.
From MOJO magazine's May 2010 interview Robbie claims he is writing an autobiography.
Martin Scorsese was hired to direct The Last Waltz based on his use of music in Mean Streets. The two lived together during the editing of Waltz and became friends. Scorsese had later admitted that during the editing process, the two used drugs heavily. Scorsese hired Robertson to compose the musical score for his 1980 film Raging Bull, and in the years since the two have been frequent collaborators. Robertson would later work on Scorsese's movies The King of Comedy, The Color of Money, Casino and The Departed, act as executive music director for Gangs of New York, and music supervisor for Shutter Island.
In 1967 Robertson married Dominique Bourgeois, a Québécoise journalist. Together they have three children: daughters Alexandra and Delphine, and son Sebastian.