Traditional singers rejoice in songs which demonstrate cleverness or outwitting someone, such as a good bluff in a gambling game. This song has been around for a long time and versions have been collected even in recent times. Early prints give it the title of “The Adventures of a Penny” but most folksingers (and folklorists) tend to call it “The Penny Wager”. Its spread is mainly confined to England but isolated versions have turned up in Australia, Ireland and the USA.
Various versions with tunes have been collected in Gloucestershire. Go to ‘Browse’ and search for 393 under ‘Roud number’.