I was looking for examples of plays on words with as many meanings as possible and found this:
… it has been suggested that Shakespeare’s play Much Ado About Nothing used this ploy to present a surface level description of the play as well as a pun on the Elizabethan use of “nothing” as slang for vagina.
A triple entendre is a phrase that can be understood in any of three ways, such as in the cover of the 1981 Rush album Moving Pictures. The left side of the front cover shows a moving company carrying paintings out of a building. On the right side, people are shown crying because the pictures carried by the movers are emotionally “moving”. Finally, the back cover features a film crew making a “moving picture” of the whole scene.
Since “moving” can also mean selling (as in moving the merchandise) and since albums are often referenced by a single word in their title (for brevity), the bands use of an appealing multiple-entendre cover could be said to be for the purpose of “moving Pictures” – and as such be a quadruple entrendre.
As a songwriter, though not rap, I have sought the lyrical white whale:
The quadruple entendre is the white whale of rap. For lyrically mined hip-hop heads, there’s no greater feat a rapper can accomplish. Some say Eminem successfully employed the much vaunted figure of speech on “Fast Lane”. Others say Kanye did so on “Blame Game”. It’s a contentious issue that impassioned heads debate endlessly in forums and comment sections, due much impart to the inherent difficulty (some would say impossibility) of imbibing a turn of phrase with such a multifaceted meaning. But it’s that very difficulty, the challenge of accomplishing the impossible, that makes it so appealing to MCs (and listeners) seeking transcendence through technique. …
Surely one can do better? I now throw my hat in the ring. Are you ready for… Xeno’s sexdecuple entendre? No kidding, sixteen different meanings:
our Mother is slipping away.
1) Mother’s in moccasins, out on the ice: our Mother is slipping away
2) The bride of my father’s not long for this life: our Mother is slipping away
3) The woman who birthed me is going cra-cra: our Mother is slipping away
4) Fewer souls now to Mother Mary pray: our Mother is slipping away
5) The orbit of the Earth is getting farther from the sun: our Mother is slipping away.
6) This planet, our home, is all but done: our Mother is slipping away
7) An enemy of ours is making an escape: our Mother is slipping away
8) We will have another brother nine months from now: our Mother is slipping away
9) She does it alone, only she knows how: our Mother is slipping away.
10) She’s been cheating on him a couple times a week: our Mother is slipping away
11) Mama made a mistake, now get out of my day: our Mother is slipping, away!
12) Her first name’s “Slipping”, second’s “Away”: our Mother is Slipping Away.
13) The source of all life is getting harder to find: our Mother is slipping away
14) Protection by government is more unkind: our Mother is slipping away
15) the role of a woman is clearly being blurred: our Mother is slipping away
16) Whistler’s oil on canvas is fading I’ve heard: our Mother is slipping away
How many meanings fit in my phrase? Sixteen at least, am I not a word beast?
To really cement this, the phrase must appear once in a context that makes all sixteen meanings clear at the same time. Impossible?