Captain W. B. Whall, 1910, is one of the few sources of this wild, provocative shanty. He identifies it as stemming from a minstrel song, and indeed, one exists with the title but a separate melody. This was a homeward bound song, and "the chorus lends itself to the occasion," although Whall acknowledges that when no passengers were on board, an "unprintable" version was sung instead. In his experience, the line "I wonder if my clothes are out of pawn" was directly substituted when necessary.
There has been much speculation about the innuendo within the verses and chorus. Stan Hugill introduced the clever entendre "Jenny keep your ringtail warm" as the ringtail is a small, aft-ship sail but also connotes vigorous lovemaking upon the return of the sailor. In the early 1900s, John Short evidently provided Cecil Sharp the line "Jenny get your oatcake done," a chorus which also appears in a mid-19th century minstrel song.
Various references within the verse trace out a particular course of navigation, but in practice, it is likely that the details of the song were composed specifically for the journey at hand.
The tune is related to Santy Anna and the structure, says Cecil Sharp, is akin to Spanish Ladies. In Sharp's version,
Lloyd's verse mentions