Bob Dylan’s first recordings date from long before the sessions for his first album. As early as May 1959 in Hibbing, in 1960 in Minneapolis, and in three other recording sessions in 1961, the songwriter has taped several songs. As harbingers of future success, these recordings have taken on great importance—and not just artistically.
The first notable pirated album of the rock era appeared in July 1969—a Bob Dylan album titled Great White Wonder. The album includes tracks recorded with the Band in the summer of 1967 and later released as Dylan’s 1975 album The Basement Tapes, other recordings made in December 1961 in Minneapolis, and a live rendition of “Living the Blues” from the Johnny Cash Show. The album had twenty-five tracks, to the delight of Dylan’s fans. As a result, Dylan was the most pirated artist in the history of rock music.
To stop this proliferation of unauthorized records and to satisfy a broad audience, Sony released the first compilation box of The Bootleg Series in 1991. The Bootleg Series Volumes 1–3: Rare & Unreleased, 1961–1991 is composed of fifty-eight songs recorded between 1961 and 1989. The Bob Dylan recording archives subsequently put out other bootlegs. Some are from live performances (volumes 4, 5, and 6), while others consist mainly of outtakes made during recording sessions for official albums and some officially unreleased songs: The Bootleg Series Volume 7: No Direction Home: The Soundtrack (2005); The Bootleg Series Volume 8: Tell Tale Signs: Rare & Unreleased 1989–2006 (2008); The Bootleg Series Volume 9: The Witmark Demos: 1962–1964 (2010), which includes recordings made at the same time as those for Columbia Records; The Bootleg Series Volume 10: Another Self Portrait (1969–1971) (2013); and the latest, The Bootleg Series Volume 11: Bob Dylan and the Band: The Basement Tapes Complete (2014).
Among Dylan’s recordings before he signed with Columbia Records in 1961, two songs appeared on The Bootleg Series Volume 7: “When I Got Troubles,” recorded in May 1959 in Hibbing, and “Rambler, Gambler,” recorded during the summer of 1960 in Minneapolis.
![]() | When I Got Troubles Bob Dylan / 1:29 |
Musician: Bob Dylan: vocals, guitar / Recording Studio: Ric Kangas’s home: May 1959 / Set Box: The Bootleg Series, Vol. 7: No Direction Home: The Soundtrack (CD 1) / Release Date: August 30, 2005
Ric Kangas, a Hibbing native, met Bob Dylan in 1958. They became close because of their mutual passion for folk and blues. They played together at various events, auditioning unsuccessfully for the Hibbing Winter Frolic, an annual festival attracting a large number of people from the Midwest. In 1959, Kangas bought a small tape recorder and a Shure microphone. In May 1959, he invited Bob Dylan, who had just celebrated his eighteenth birthday, to record some songs at his home. Four songs were recorded that day: Dylan solo for “When I Got Troubles” and “I Got a New Girl,” Dylan and Kangas for “I Wish I Knew,” and Kangas solo for “The Frog Song.”
“When I Got Troubles” is the only song from the improvised recording session included in The Bootleg Series Volume 7. The song reveals the overwhelming blues influence on Dylan, in particular blues songs from the pioneers in the Mississippi Delta. In this first recording Bob does not have the assurance of a professional musician. His voice remains in a lower register, almost confidential in style, and the guitar playing is quite poor. Yet an impression of depth emerges from his interpretation. Dylan believes in his own talent, and, of course, the future will prove him right.
![]() | Rambler, Gambler Traditional / Arrangement Bob Dylan / 2:28 |
Musician: Bob Dylan: vocals, guitar, harmonica / Recording Studio: Cleve Petterson: 1960 / Set Box: The Bootleg Series, Vol. 7: No Direction Home: The Soundtrack (CD 1) / Release Date: August 30, 2005
In the early 1950s, Cleve Petterson was a regular in the Minneapolis clubs and, as such, had contact with folksingers hanging out in Dinkytown. During the summer of 1960, he asked Bob Dylan, an unknown folksinger at the time, to record on his tape recorder twelve folk songs from Woody Guthrie and Jimmie Rodgers’s repertoire.
One of the songs was “Rambler, Gambler.” It was known under a variety of titles, such as “The Rambling Gambler” and “I’m a Rambler, I’m a Gambler.” This folk song was first released by John and Alan Lomax on their 1938 album Cowboy Songs and Other Frontier Ballads. Alan Lomax recorded his own rendition for his 1958 album Texas Folk Songs. Dylan recorded the song two years later, followed by notable performers, including Odetta, Joan Baez, Simon and Garfunkel, Flatt & Scruggs, and the Clancy Brothers. At age nineteen, the singer and guitarist already recognizes in himself the character of a western American—a traveler and poker player, loner and freedom-lover.
In this traditional folk song, he offers an interpretation with a Woody Guthrie style. Country guitar, lyrical voice, reconciliation—the progress is obvious. He has already mastered a very credible sort of finger-picking, and the quality of the recording is much better than “When I Got Troubles.” He still, however, needs to find his own identity.