Pretty Peggy-O is the second song presented here from Bob Dylan’s debut record after the previous entry Baby, Let Me Follow You Down. For me Pretty Peggy-O was the surprise packet upon rehearing the record many years later. Understandably the songs like Song to Woody (an ode to his folk hero Woody Guthrie who was a significant influence in his early career) and his rendition of House of the Risin’ Sun may be more widely recognised but today I would like to focus on this lesser known traditional folk song. Pretty Peggy-O is perky and animated and I can’t help but admire Dylan’s brazen, but high-spirited harmonica playing here. There are also some amusing expressions which I get a buzz out of.

Peggy-O is a southern american version arranged for the harmonica of an unattributed Scottish folk song The Bonnie Lass o’ Fyvie. It is about a thwarted romance between a soldier and a girl. He starts off the song with the introduction “I’ve been around this whole country but I never yet found Fennario“, as a playful remark on the fact that the song has been borrowed and cut off its original “setting”. Dylan began playing the song live again in the 90s, using the lyrics and melody of the Grateful Dead version.

I’ve been around this whole country
But I never yet found Fennario

Well, as we marched down, as we marched down
Well, as we marched down to Fennerio’
Well, our captain fell in love with a lady like a dove
The name that she had was pretty Peggy-O

Well, what will your mother say, what will your mother say?
What will your mother say, pretty Peggy-O?
What will your mother say to know you’re going away?
You’re never, never, never coming back-io? (Read the remainder here)

The following is cherry picked from the second Wikipedia reference below:

Bob Dylan’s debut album was produced by John H. Hammond who had earlier signed Dylan to the label, a controversial decision at the time. Dylan met John Hammond at a rehearsal session for Carolyn Hester on September 14, 1961. Hester had invited Dylan to the session as a harmonica player, and Hammond approved him as a session player after hearing him rehearse, with recommendations from his son, musician John P. Hammond, and from Liam Clancy. Hammond later told Robert Shelton that he decided to sign Dylan “on the spot” and invited him to the Columbia offices for a more formal audition recording.

The album was ultimately recorded in three short afternoon sessions on November 20 and 22 at Columbia’s 7th Avenue studio. Hammond later joked that Columbia spent “about $402” to record it, and the figure has entered the Dylan legend as its actual cost. Despite the low cost and short amount of time, Dylan was still difficult to record, according to Hammond. “Bobby popped every p, hissed every s, and habitually wandered off mike,” recalls Hammond. “Even more frustrating, he refused to learn from his mistakes. It occurred to me at the time that I’d never worked with anyone so undisciplined before.”
The album did not receive much attention at first, but it achieved some popularity following the growth of Dylan’s career, charting in the UK three years after its release, reaching No.13.

References:
1. The Bonnie Lass o’ Fyvie – Wikipedia
2. Bob Dylan (album) – Wikipedia