MEANINGS

 

The phrase to pile, also to heap, Pelion upon Ossa, and variants, mean to add difficulty to difficulty, also, to add to what is already great.

This phrase occurs, for example, in Just put a royal sock in it, Sarah, by Judith Woods, published in The Daily Telegraph (London, England) of Wednesday 9^th March 2011:

Who would want to be the Duchess of York’s PR this week? Short of being caught in a YouTube tryst with Charlie Sheen, snorting cocaine off a hooker in a hot tub, Sarah Ferguson’s stock could not conceivably sink any lower.
At a time when her beleaguered, though still swaggering, ex-husband, the Duke of York, is fighting for his future as Britain’s trade ambassador, her blunderingly gauche attempt to “support” him has merely piled Pelion upon Ossa.

 

ORIGIN

 

Pelion and Ossa are two mountains in Thessaly, in northern Greece, and the phrase to pile, also to heap, Pelion upon Ossa, alludes to Greek mythology: two giants, Otus and Ephialtes, tried to pile Pelion and Ossa on Olympus in order to reach the gods and overthrow them.

The story is told in the Odyssey, a Greek epic poem, attributed to Homer, a semilegendary Greek poet of the 8^th century BC, describing the ten-year homeward wanderings of Odysseus after the fall of Troy:
—from The Odyssey. Rendered into English prose for the use of those who cannot read the original (London: A. C. Fifield, [1900]), by Samuel Butler:

Otus and Ephialtes […] threatened to make war with the gods in Olympus, and tried to set Mount Ossa on the top of Mount Olympus, and Mount Pelion on the top of Ossa, that they might scale heaven itself.

In the Georgics, by the Roman poet Virgil (Publius Vergilius Maro – 70-19 BC), the giants try to pile Ossa on Pelion, and Mount Olympus on Ossa:

ter sunt conati imponere Pelio Ossam
scilicet atque Ossae frondosum inuoluere Olympum
     translation:
Thrice they tried to pile on Pelion Ossa, and on Ossa to roll leafy Olympus.

 

EARLY OCCURRENCES

 

The phrase is first recorded, as to heap Pelion upon Ossa, in Chapter VI, How a Gallant should behaue himsefe in a Play-house, of The Guls Horne-booke (London: [Nicholas Okes] for R. S[ergier?], 1609), by the English playwright and pamphleteer Thomas Dekker (c.1572-1632):

It shall crowne you with rich commendation to laugh alowd in the middest of the most serious and saddest scene of the terriblest Tragedy: and to let that clapper (your tongue) be tost so high that all the house may ring of it: your Lords vse it; your Knights are Apes to the Lords, and do so too: your Inne-a-court-man is Zany to the Knights, and (many very scuruily) comes likewise limping after it: bee thou a beagle to them all, and neuer lin snuffing till you haue sented them: for by talking and laughing (like a Plough-man in a Morris) you heape Pelion vpon Ossa, glory vpon glory.

The second-earliest occurrence of the phrase is from Theatrum Redivivum, Or The Theatre Vindicated (London: Printed by T. R. for Francis Eglesfield, 1662), by the English religious writer and historian Richard Baker (c.1568-1645):

Neither Tertullian, nor any of the Fathers, did ever any otherwise condemn Plays, but as they condemned all artificial delights of the world, aspiring onely to that perfection, of which St. Iohn speaks; Love not the world, neither the things of the world: if any man love the world, the love of God is not in him. I speak this the rather for prevention; lest the man, vouchsafing perhaps to read this Discourse, should think he had found here a just ground for a Reply, and vex us again with transscribing [sic] of Authours, and heaping up Mountains of Authorities, like Pelion upon Ossa, to this purpose: which now, he may hereby know, will serve him to no purpose; for we seek to justifie Plays, as fit recreations for an honest Natural, or Moral man, but no ways to be matched with the high mysterious Contemplations of a Christian in Divinity.