Songfacts®:

• This is one of the first songs Dylan ever recorded. He was 18 years old at the time and recorded at the Hibbing, Minnesota, home of his friend, Ric Kangas, in May 1959. The two young men recorded four songs that day, including this one, "I Got A New Girl," "I Wish I Knew," and "The Frog Song" (which was all Kangas playing), with only "When I Got Troubles" making it onto the Bootleg Series Vol. 7, released in 2005.
  
  Dylan and Kangas met the previous year (1958) and played some shows together. They also tried out for the Hibbing Winter Frolic, which was a big event that drew crowds from all around Dylan's hometown of Hibbing, but didn't make the cut.
• "When I Got Troubles" is a blues song. The lyrics are simple and straightforward, talking about "swinging" one's troubles away, presumably meaning dancing.
  
  The song shows no hint of the elliptical lyricism for which Dylan would soon become famous, but it does show the young man's (he was only eighteen at the time) deep interest in Delta blues.
• In addition to the poor quality of the recording itself, Dylan's guitar-playing is choppy here, and his singing is unremarkable, not yet showing the divisive, yet inarguably attention-grabbing nasally vocal style that eventually made him one of his era's biggest stars.
  
  It's clear, though, he's not messing around. This recording shows the work of a young man who believed in himself and took his craft seriously. Less than three years later he would be in New York City cutting his self-titled debut album.