Pretty Peggy-O: The Best Grateful Dead Cover Song Ever

Of the 190 covers the Grateful Dead played in their concerts, none is more haunting than “Pretty Peggy-O”, sometimes known as “Fennario”.

This folk song of unrequited love is certainly my favorite Dead cover, and I’m as fascinated by the provenance of the song as I am enthralled hearing Jerry and the band play it. I listened to a lot of Dead while researching my crime novel The Haight, and this is one song I can enjoy in a loop all day long. Click on the image and judge for yourself.


“Pretty Peggy-O” is an American folk song derived from the traditional Irish ballad “The Bonnie Lass of Fyvie”. (Here’s the original being sung by the terrific Scottish folk group, The Corries.) At some point, someone brought the song across the Atlantic and over the generations it evolved into Americana. The song in various forms was a standard in the early sixties by such Greenwich Village standard-bearers as Bob Dylan (who sang it on his debut album), Joan Baez, Simon and Garfunkel and Makem and Clancy.

But the Dead – especially Jerry Garcia – made this song their own. They played it on 265 known occasions, and Jerry’s gentle voice and searing guitar are perfect for the mellifluous drift of the ballad. The band’s laid-back tempo gives it a classic Dead feel, like “Ship of Fools”. Jerry recorded the song as “Fennario” on Run for the Roses.

“Pretty Peggy-O” tells the story of soldiers leaving a place called Fennario.  There’s no such place in the real world, and David Dodd points out in The Annotated Grateful Dead Lyrics that it is probably derived from the British word “fen”, which refers to flat, muddy lands, especially around Cambridgeshire. The strange name caused Dylan to say in his intro, “"I've been around this whole country but I never yet found Fennario.” Maybe the Dead did find it, as they mentioned the place again on “Dire Wolf” on Working Man’s Dead.

As they left Fennario, a captain called William falls in love with a young woman called Peggy, and asks for her hand in marriage. She declines, saying he is too poor, and he swears vengeance if he ever returns. She later learns the soldier has died, having fallen in love with another woman in Louisiana.

No one ever played the song better than the Grateful Dead. My favorite version of the song is from the May 1977 concert at the St. Paul Civic Center, though some people prefer the xxxx.

Here are a few other covers of the song by other artists. None can compare with the Dead’s version, but they’re interesting.

Simon and Garfunkel

Joan Baez

Bob Dylan

Peter MoreiraComment