Songs like these, as much as any of the true classic originals or the world-famous albums, tell us a lot about Bob Dylan and the world he's constructed for himself. "Pretty Peggy-O" has a pretty rich history, starting as a Scottish folk song about love unrequited and heartbreak and all that good stuff and slowly mutating into a Civil War Dixie song about, well, love unrequited and heartbreak and all that good stuff. As you might imagine, a song with that kind of pedigree (not to mention a sweet, charming melody) would be popular amongst folk musicians, and it shouldn't be much of a surprise that Dylan would appropriate it (excuse me, "trad. arrange" it) for his debut album. If nothing else, it's a nice respite from the heavier blues stuff, even if the lieutenant pining for Peggy-O does kick it in the end.
But it isn't just the fact that Dylan played the song on his debut that gives "Pretty Peggy-O" some heft in Dylan's career. It's the fact that, a good many years later, Dylan would pull the song out of mothballs and play it on stage that lends the song an additional dimension. Dylan, for those of you that might not know (and I doubt there will be many that read this damn thing), liked to pull out obscure folk songs to play during his concerts in the late-90s and early 2000s, often as the opening tune; I wonder why he more or less has stopped doing that. There are plenty of reasons why he'd use up a slot he could play one of HIS own obscurities in for these kinds of songs, of course - partially in tribute to the songs that influenced him in his formative years, partially in tribute (maybe) to the Grateful Dead, who peppered their setlists with traditionals as well (including, surprise, "Pretty Peggy-O"), partially because the songs are fun and easy to play and serve as showcases for his always-talented bands, and partially because he's Bob Dylan and can do whatever the hell he pleases. They serve both as strong tunes and as history lessons, a way for Bob to say "this is what I listened to when I was your age, you whippersnappers". Plus, you know, sometimes he just wants a six-minute breather before he plays "Like A Rolling Stone" for the millionth time.
Having only been familiar with the live version of "Pretty Peggy-O" (a stately version with bubbling guitars and Dylan's strangely comforting sandpaper growl of a voice), I was surprised to hear just how exciting the Bob Dylan version is. Starting with a cheeky spoken word intro ("I've been around this whole country/But I never yet found Fennario" - sure you have), Dylan basically chugs his way through the song, adding "woo-hoo"s for emphasis and quite possibly nearly snickering at one point. His harmonica playing, in particular, is rather energetic, full of trilling notes and as simplistic as you'd expect from a man his age (it doesn't help that it sounds out of tune). Dylan, for whatever reason, seems to LIKE playing this song, and it shows in the performance.
The lyrics don't particularly make sense to me - so, okay, this army troop's marching to a town called Fennario, then the captain falls in love with a woman, but I guess she runs away or something, and then the lieutenant's in a rodeo, and then the captain dies pining for Peggy-O and is buried in Louisiana...hmm. Not exactly "A Farewell To Arms", is it? I suppose the lyrics aren't the point, when you can hear just how much fun Bob's having blowing away on his harp, snapping off the "o"s at the end of every verse (the way he says "back-io", almost like he's trying to cram it into one syllable, is a hoot), and wailing away on his guitar. Another highlight of the album, then. I guess it's not hard to see why Bob would revisit the song.
AUDIO BONUS: From fabled bootleg Bathed In A Stream of Pure Heat, here's "Pretty Peggy-O" from Albany, NY on April 18th, 1997. Gotta love Bob on solo guitar!