Lyrics: Traditional
Music: Traditional
A traditional song performed by Jerry Garcia with the Grateful Dead from the late 70s, and also with some of his solo bands.
There was a wealthy merchant, in London he did dwell
He had a beautiful daughter, the truth to you I'll tell
Oh the truth to you I'll tell
She had sweethearts a plenty and men of high degree
But none but Jack the sailor her true love e'er could be
Oh her true love e'er could be
Jackie's gone a sailing with trouble on his mind
He's left his native country and his darling girl behind
Oh his darling girl behind
She went down to a tailor's shop and dressed in man's array
She climbed on board a vessel to convey herself away
Oh convey herself away
Before you step on board Sir, your name I'd like to know
She smiled all in her countenance 'they call me Jack A Roe'
Oh they call me Jack A Roe
I see your waist is slender, your fingers they are small
Your cheeks too red and rosy to face the cannonball
Oh to face the cannonball
I know my waist is slender, my fingers they are small
But it would not make me tremble to see ten thousand fall
Oh to see ten thousand fall
The war soon being over, she went and looked around
Among the dead and wounded her darling boy she found
Oh her darling boy she found
She picked him up all in her arms and carried him to town
She sent for a physician who quickly healed his wounds
Oh who quickly healed his wounds
This couple they got married, so well they did agree
This couple they got married, so why not you and me
Oh why not you and me
Very early versions of the song go under a variety of different titles. One is "Jack Munro" - the following lyrics come from the Bodlean Library's ballad collection - and reveals some twists not present in the version played by the Dead. It is dated between 1774 and 1825."Another traditional song performed by the Grateful Dead is "Jack-A Roe," also known as "Jack Went A-Sailing." It is a ballad, like "Peggy-O," and, as befits the ballad form, starts out with what seems a tragic situation. This song tells the story of a woman forbidden by her father to see her lover, but who dresses as a man to follow him, a sailor who has been called to sea. Unlike most ballads, however, the song has a happy ending: she finds him wounded after a battle and takes him to a doctor who heals him and the reunited couple marries. Several versions, all collected in the United States, are given in Sharp's English Folk Songs from the Southern Appalachians, The version performed by the Grateful Dead leaves out details regarding the possessive father, although they include the first verse, they omit the following:
Her father heard the callin',
So quickly he came in.
Good morning, Mrs. Frasier,
Is that your sweetheart's name?
I will lock you in my dungeon,
Your body I'll confine
If there is none but Jacky Frasier
That will ever suit your mind.You can lock me in your dungeon,
It is hard to be confined,
But there is none but Jacky Frasier
That will ever suit my mind.
In Chatham town there lived a worthy merchant manThis was a piece by David Smyth published in the Financial Times on 2 November 2025 under the title "Jack-A-Roe - a story of love and cross-dressing on the high seas"
He had an only daughter as you shall understand
This lady was courted by many a noble knight
But there was none but Jack the sailor could gain her heart's delight
Her waiting maid standing by unto her father went
And told him the secret, his daughter's whole intent
He call'd on his daughter with pride and disdain
Saying, good morrow, Mrs Fraser, this was her lover's name
Is this the news my daughter that I have heard of thee
Young Jack he shall be pressed and you confined be
It's here is my body, you shall it then confine
There's none but Jack the sailor can gain this heart of mine
It's here is twenty guineas, I give it to thee
If you'll press young Jack to the wars of Germany
As Jack has gone on board he'll never more be seen
I will wed at your disposal if you will set me free
It's now she's set at liberty dressed in man's array
Looking for an officer to carry her away
Jack is on board with a sore and troubled mind
For the leaving of his country and darling close confined
Your name we must have sir, before on board we go
That you shall have quickly, it is Jack Munro
This lady's gone on board with a troubled mind
To land in French Flanders it is her wish'd design
Now she's landed over, reviewed for to be
Standing in the ranks her own true love for to see
She stepped up unto him, and thus to him did say
By your features an Englishman you are
If that you be willing whatever may betide
I'll be your loyal comrade and lie down by your side
The drums did beat, and the trumpets did sound
Unto the field of battle they were called along
They fought on with valour, they fought courageously
Until two officers and a private by her side did lay
The officers took notice and unto her did say
For the valour you have shown preferred you shall be
A major's commission unto you we'll bestow
And you may push your fortune brave Jack Munro
Looking through the wounded men her own lover did see
She says loving comrade they have preferred me
A major's commission unto me they will bestow
The doctor that can cure you shall be paid by Munro
She called for a minister and bade them step aside
And would call them up again when he woo'd bride
It's I'll not be groom but groom's man I'll be
For I never will be married till my Molly I do see
She stripped down her snow white breast some private marks to show
Saying Jack won't you marry me Jack don't you know
The drums did beat and the trumpets did sound
And home to Old England they were all call's along
It's now there landed, the people all went to see
Saying yonder comes the heroes from the wars of Germany
As they were walking up the street, her father he did know
Saying good old merchant will you lit with Munro?
It's out spoke the mother, I had a daughter gay
There's not a feature in your face but resembles she
It's now they got married and lie side by side
The officers and privates begrudge Jack of his bride
When the queen heard of this she laughed heartily
Saying here is fifty guineas I'll give to that lady
"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 "Jackar", "The Maid of Chatham", "Jack Went A-Sailing", "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 descendants.
There are three main characters: a wealthy London merchant, his "lovely daughter" who calls herself "Jack Munro" or, when disguised as a man, "Jackaro", 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 sow confusion on the high seas, though George Davis, the "singing miner of Kentucky", decreed on a 1967 album that her real name was Polly.
When Jack the sailor goes off to war (in some versions he is press-ganged), the daughter heads to a tailor's shop, gets kitted out in "men's array" and lands a place on another ship. This is where she joins a long line of heroic women making a fine fist of jobs traditionally considered men's work, including Joan of Arc, Viola in Shakespeare's Twelfth Night, and the England women's 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 of folk singers and song collectors preserved it in recordings made by both Jean and her older sister Edna.
The first modern recording was made in 1957, on an album by Jean Ritchie, Oscar Brand and Tom Paley; this version includes an extra verse revealing that it was all dad's fault: "Oh daughter, oh daughter, your body I'll confine/If none but Jack the sailor would ever suit your mind," the villain says. 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. In the version Joan Baez sang on her In Concert album of 1963, Jack seems to go sailing of his own accord "with trouble on his mind".
It's strongly associated with The Grateful Dead and pops up often in their bootleg-heavy discography, though they don't seem to have played it earlier than 1977. The energetic acoustic recording on their 1981 live album Reckoning is the best known, but it's also worth seeking out a studio out-take 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, an album of traditional covers. Back on his acoustic guitar and harmonica, he ought to have reminded listeners of his 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. 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.