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We now often hear phrases like:
That's pretty interesting.
The word "pretty" here is used to say "somewhat," "considerably/rather," or something along those lines (if a little stronger).
However, this definition doesn't appear in any dictionary I've searched.
What is the earliest known use of this form? More generally, how did this use of "pretty" come about?
As FumbleFingers says, this is a pretty old use, going back to Early Modern English:
Pretty (pri•ti) adv. Forms: see prec. [The adj. in adverbial use.]
1. To a considerable extent, considerably; in a fair or moderate degree, fairly, moderately, tolerably; [...]
1598 FLORIO Dict. Ep. Ded. 3 Boccace is prettie hard, yet understood: Petrarche harder but explained. —OED 1
(I offer this OED 1 citation rather than the earlier one reproduced by FumbleFingers because I am not convinced that the use in the earlier citation is adverbial.)
Pretty has a complicated history, as you may see from the OED 1 entry which immediately precedes the link above: from cunning, artful to clever, skilful to ‘a general epithet of admiration or appreciation... fine, pleasing, proper’, and so forth, leading to the main modern sense ‘having beauty without majesty or stateliness’; but the origin of this adverbial use clearly lies in OED 1 sense 5 for the adjective:
5. Considerable in number, quantity, or extent, as in a pretty deal, while, way, etc.; also a pretty many = a good many; ...
OED 1 gives citations for this use dating from c. 1485 down to 1861, but marks it as ‘Now arch. or dial.’
I am surprised you did not find this in any dictionary; I found it in the first three online dictionaries I checked, Collins, Oxford, and Merriam-Webster. All three post definitions for the adverb after those for the adjective.
Perhaps it has to do with French influence after the Norman conquest from the expression "près de" (near) since it means "close to" or "right up to"? I have NO evidence of this. Does anyone? This just came to mind.
I think it goes back much further, to the Latin 'pretiosus' meaning pricy, valuable, expensive - hence its early adjectival use in the phrase 'a pretty penny'. Pretiosus comes from the Latin 'pretium' meaning a price. Smith's Latin Dictionary has pretiosus right back in Cicero in the first century BC, and points out that 'pretium' goes right back to a Sanscrit rooot. Similarly the word 'dear' means both 'beloved' and 'expensive'. Possibly its meaning changed once the use of money became normalised, and this brought in the developed meaning Please prove me wrong, someone! it would be good to know if the earliest Early English usages were in areas where the Romans were in control, for example.
Regarding the phrase "pretty please", I believe that the origin comes from a variation of the request : "I pray thee, please." "I pray thee "morphed into the single word: "prithee". Prithee is a very old contraction that was used in Shakespeare. Thus "prithee please" then became "pretty please". This is a personal conjecture, but one that rings true.
John Kelly's ODO article explains the semantic shifts. BTW, Anatoly Liberman's doesn't..
What in the Word?! ‘Pretty’ is… not quite as pretty does
That’s a pretty dress. I’m pretty sure I locked the car. Her new watch cost a pretty penny. We came to a pretty pass in our negotiations. How does this pretty manage to mean ‘attractive’, ‘considerably’, ‘expensive’, and ‘difficult’ all at once? It’s a tricky little word – literally so.
Language, if there’s one thing we can say about it, is constantly changing. And not even the core meanings of some English’s most basic words are safe from language’s inexorable flux. Take nice. It meant ‘foolish’ 600 years ago, undergoing a type of semantic change called amelioration. Or silly, which started out as ‘happy’ or ‘fortunate’, an example of semantic pejoration. Handsome, as we explored in the inaugural post of this series, began as ‘easy to handle’.
Pretty joins this incredible group. If we time-travelled to an Anglo-Saxon village, wandered around its thatched huts, smithies, and rows of barley, and listened to folks speak, we wouldn’t recognize the word pretty. For one, in one of its Old English forms of prættig, it would have sounded very different, something like ‘prat-teeh’. For another, it meant ‘clever’ or ‘cunning’. Yes, pretty was originally a crafty word.
A ‘trick’ up its sleeve
The word pretty has its roots in prat, a word for ‘trick’ or ‘prank’, and features the common adjective suffix -y. The word prat is Germanic, with living cognates in the likes of the Dutch prettig (‘nice, pleasant’). It bears no relation to prattle or, alas, pratfall, whose prat is actually an old slang term for the buttocks.
The ‘tricky’ prat really only survived in the Shetland dialect up until the mid-1900s or so – and in names. The surname Pratt, like actor Chris Pratt, apparently originated as a byname for someone ‘full of wiles’. The proto-Pratt must have been the village tinkerer, always cooking up some scheme.
Surnames are indeed noteworthy in the history of pretty. As the Oxford English Dictionary observes: ‘Between the end of the Old English period and the 15th cent. the word is only attested in surnames (e.g., Simone Praty (1301), Henry Praty (1304), Johannes Pratyman (1343), and Willelmus Pritty (1428))…’
Mr Willelmus Pritty, for one, appears to reflect the modern pronunciation of the word. Pretty is also an example of another linguistic oddity, where the modern spelling and pronunciation reflect different pathways in the word’s (very complicated) form history.
Why the gap? We can only speculate. The record only preserves what was written – and historically, what was deemed important to be written. We should remember that writing was a rare skill in the Middle Ages and permanent writing was done on expensive parchment, reserved for the loftier and more formal subjects of religion, law, finance, and poetry. Pretty, for whatever reason, didn’t make the cut, except for our friends Johannes and Willelmus, with their names scratched into feudal ledgers or the like.
That all changed by the mid-1400s, when the OED finds evidence for a range of emerging senses of pretty. And there is a logic to its progression. Something ‘tricky’ can be seen as ‘clever’, and something ‘clever’ can
we[typo] be well made, which is ‘pleasing’ to the eye. This ‘attractive’ pretty is attested of people, especially women and children, by 1440, in the same source that gives us the earliest record of handsome so far, the English-Latin bilingual dictionary Promptorium Parvulorum: ‘Praty, elegans, formosus, elegantulus, formulosus’, i.e., elegant or finely formed, with a suggestion of daintiness or delicacy.By at least 1475, pretty was characterizing things as exactly the opposite of small and intricate – as ‘considerable’ or ‘sizable’, e.g. a pretty many or, come the 1700s, a pretty penny. We see a similar jump in other ‘attractive’ or ‘worthwhile’ descriptors: a fair amount, a good many, a handsome sum.
Talking pretty
From here, pretty made its next jump, hopping grammatical categories from adjective to adverb. This development isn’t exactly a giant leap, though, as it’s a short step from ‘considerable’ to ‘to a considerable extent’, recorded in the latter half of the 16th century. Very undergoes a parallel evolution from an adjective for ‘true’ to an adverb for ‘to high degree’.
What’s interesting, though, is how pretty became more widespread than its expected adverbial form, prettily, attested by 1450. It originally meant ‘skilfully’ and is now mainly, if infrequently, used for ‘politely’ or ‘charmingly’. What’s also interesting is the subtlety of the adverbial pretty. Think of it this way: How would you explain the differences among good, pretty good and very good to a non-native English speaker? It talks and sits pretty, pretty.
The same goes for the adjectival pretty: How would you teach an English-language learner when to use pretty vs. beautiful? What connotations would you tell your student to mind? How about who we call pretty, a term, for better or worse, reserved for women just as handsome is for men (e.g. pretty boy)?
Pretty also made the jump to noun, an ‘attractive thing’ (e.g., my pretty) or ‘a large amount of money’. Some golfers also called the fairway a pretty in the early 20th century. Pretty, too, inspired a verb, prettify, as early as 1661 and pretty up by 1863.
Pretty didn’t completely shed all its original ‘subterfuge’ over the centuries, however. By the early 1500s, pretty came to describe something as ‘awkward, difficult, or unwelcome’, a sense which survives in phrases such as a pretty mess, a pretty pass, or a pretty kettle of fish. And every now and again, US sports writers will call an athlete a pretty player, not referring to looks but skill, a sense of pretty lingering from the 15th century.
Purty and pooty
And what about, finally, purty? Is that just the ignorance of some bumpkin or the drawl of the cowboy? The OED finds purty in British writer Aphra Behn’s 1682 comedic play, The City Heiress – not exactly the backwoods or Wild West. This sound-switching of pretty’s ‘r’ and vowel has a name, metathesis, and gave us bird from its original brid and third from thrid.
Pooty is another variant pronunciation of pretty founded in the 1820s – dropping the tricky ‘r’ altogether, something Old English occasionally did, as we can find pæti for pretty in the record. But let’s not worry our pretty little heads about the loss of ‘r’s in Old English consonant clusters, pretty please
