LIFE OF A SONG – ‘Jack-a-Roe’ – Financial Times, 2 Nov 2025

If you’ve ever made or received a marriage proposal, it’s likely there was a grand plan conceived for the big question. It’s less likely, however, that the plan included a long story about a cross-dressing woman who took to sea to rescue her boyfriend from a war. “This couple they got married/And well they did agree/This couple they got married/So why not you and me?” the narrator concludes at the end of this dramatic folk tale. As chat-up lines go, it’s an odd one.

“Jack-a-roe” is a traditional ballad that first appeared in print in England around 1818 and in the US in the 1830s, so it’s no wonder the song’s long evolution has left it with a range of different titles. It has also been known as “The Maid of Chatham”, “Jack Went A Sailing”, “The Soldier Maid”, “Jack Munro” and “Jack the Sailor” among other things. The bones of the story have stayed the same, though, from the original folk collectors through to the revivalists of the Sixties and their descendents.

There are three main characters: a wealthy London merchant, his “lovely daughter” who calls herself “Jack Munro” or “Jackaro” once disguised as a man, and her “true love”, known as either “Jack the sailor” or “Jackie Frazier”. With two people called Jack, it’s no wonder they were able to sew confusion on the high seas, though George Davis, the “singing miner of Kentucky”, decreed on a 1967 album that her real name was Polly.

In the version Joan Baez sang on her In Concert album of 1963, Jackie seems to go sailing of his own accord “with trouble on his mind”. But Tom Paley sang the first modern recording in 1957, on a collaborative album with the preserver of Appalachian folk music Jean Ritchie, which includes an extra verse revealing that it was all dad’s fault: “Oh daughter, oh daughter, your body I will confine/If none but Jack the sailor would ever suit your mind,” the villain says.

The daughter heads to a tailor’s shop, gets kitted out in “men’s array” and lands a place on another ship sailing to war. This is where she joins a long line of heroic women making a fine fist of jobs traditionally considered man’s work, including Joan of Arc, Viola in Shakespeare’s Twelfth Night, and the England football team. The most inspiring verse comes when she is accused of being too dainty to survive in a war zone. You can imagine the steel in her eyes when she replies: “I know my waist is slender/My fingers neat and small/But it would not make me tremble/To see ten thousand fall.”

So she reaches the battlefield, finds wounded Jack, carries him to a doctor and as we already established, they marry. The story has been told by numerous women and men over the years. There’s a crackly, spooky recording made by the musicologist Alan Lomax in 1937, sung by a young woman named Nora May Begley from Kentucky’s Pine Mountain settlement school. Later, Kentucky’s Ritchie family preserved it in recordings made by both Jean and her older sister Edna. In 1961, Peggy Seeger and her partner Ewan MacColl united the song’s British and American roots on their album Two-Way Trip: American, Scots and English Folksongs.

Some other giants of the Sixties tackled it, but not til later. It’s probably most strongly associated with The Grateful Dead and pops up multiple times in their bootleg-heavy discography, though they don’t seem to have played it earlier than 1977. You can find Deadheads online arguing about whether the better version is “5/17/77” or “5/26/77”. The energetic acoustic recording on their 1981 live album Reckoning is the best known, but it’s also worth seeking out a studio outtake from 1979 which has an almost reggae swing. More recently the English folk musician Kate Stables, who trades as This is the Kit, picked it as her contribution to the lengthy, excellent 2016 Grateful Dead tribute album Day of the Dead.

Bob Dylan didn’t get around to it until 1993, when he was at something of a commercial low point on World Gone Wrong, his second album in a row of traditional covers after Good As I Been to You. Back on his acoustic guitar and harmonica, he ought to have reminded listeners of his earliest days as folk’s golden boy, but his voice at this point was more of a sepulchral croak.

The song was called “There Was a Wealthy Merchant” and given some unnecessary production polish by Steeleye Span on Bedlam Born in 2000. Much more recently, in 2021 the British singer-songwriter Polly Paulusma showed there is still life in the tale after centuries, giving “Jack Munro” a fresh tune and some juicy additional detail. This time the daughter robs her father and once at war, gets herself promoted to Colonel. There’s no glass ceiling in this empowering classic.