Songfacts®:

• This was one of two original songs on Bob Dylan's eponymous first album. It describes his feelings on arriving in New York, and the initial difficulty he had finding gigs.
• The line, "Now, a very great man once said, that some people rob you with a fountain pen," is a nod to Dylan's hero, Woody Guthrie. It is a specific reference to "Pretty Boy Floyd," Guthrie's 1939 ballad about the 1930s gangster.
• The spoken narrative form of this song is an example of a genre often referred to as "talking blues." Christopher Allen Bouchillon pioneered the form with songs like "Talking Blues" from 1926, but folk legend and American cultural touchstone Woody Guthrie was the most prominent user of the style. Guthrie was Dylan's idol, so it's likely the young Dylan took inspiration from him, but Dylan was also a serious folk-music scholar and probably was aware of Bouchillon as well.
• Dylan wrote this in May 1961 at a time when he was traveling outside of New York.
  
  So long, New York
  Howdy, East Orange
  
  East Orange is a city in New Jersey. Dylan mentions the place because it was where Bob and Sidsel Gleason lived.
  
  The Gleasons were a married couple who took Woody Guthrie home on weekends when Guthrie was living in the Greystone Park Psychiatric Hospital, where he'd been placed because of his Huntington's disease. With Guthrie's visits, the Gleason home became a kind of hootenanny where prominent folk musicians such as Pete Seeger, Harold Leventhal, and Alan Lomax would hang out and play music, while young folk musicians would sleep there. Dylan himself lived there for a few weeks. Legend has it that the Gleasons gave Dylan one of Guthrie's old suits to wear for his debut at Gerde's Folk City in New York.
• Dylan did two takes of this song in the recording studio. The one on the album is the second take.
• This is the only song on the Bob Dylan album that ends with a fade-out.