I love the "Lady Leroy" which has two versions in the DT. I've heard the second one done by an Irish group: "Oisin".

In this song the rich woman disguises herself as a man to buy a ship from her own father to run off with her sailor. The father sends one of his captains after them, they fight, the Lady Leroy (the name of the ship, not the woman) wins and they escape to Boston:

Here's a health to pretty Polly! Long may she enjoy Her proudest of heros and the Lady Leroy

judy