In an advertising poster, for actual apples:
(#1)
and on a tongue-in-cheek sticker, reproducing a gloat:
(#2)
Both incorporate phonological reductions of casual speech — ’bout for about, d’ya ([djǝ] or [ǰǝ]) for do you — and also one feature of “demotic American” (a collection of linguistic features widespread in working class speech): determiner them (in place of standard those). But even without the phonological reductions we’re left with two formulaic expressions —
How about them apples? What do you think about them apples?
that are available for English speakers in general (not just working class speakers), not as opinion-seeking questions like
How about those apples? What do you think about those apples?
but as conveying one or the other of two types of gloats (directed by the speaker against the addressee).
Assembled from material on the Free Dictionary site, on the idiomatic expressions How do you / d’ya like them apples? and How about / ’bout them apples?
(a) A phrase used to draw attention to one’s cleverness or superiority to the one being addressed, especially after a recent triumph. You remember how you said I would never get into law school? Well now I’m valedictorian. How do you like them apples? [similarly, What do you think about them apples?]
(b) Used after telling somebody an unpleasant fact or truth, to say that they should accept it: Either you deliver the dresses for the price we agreed on, or I’m going to go someplace else. How do you like them apples? [similarly, What do you think about them apples?]
From NOAD:
verb gloat: [no object] contemplate or dwell on one’s own success or another’s misfortune with smugness or malignant pleasure.
noun gloat: [in singular] informal an act of gloating.
Ordinary opinion-seeking wh questions can be pressed into service as indirect gloats — How about that? What do you think about that?, or How do you feel about that?, What are you going to do about that?, and so on. But with the idiomatic direct object apples in combination with the determiner them instead of those, the expressions can be imported from working class speech (where they’re ambiguous between opinion-seeking questions about apples, on the one hand, and gloats, on the other) as a kind of quotation in standard speech, interpretable there only as gloats. That’s the way they work for me.
Use (a) is straightforwardly gloating. Use (b) is somewhat more complex: the speaker presents the addressee with some observation the addressee will find unpleasant and then rubs it in, insisting that the addressee accept it. Conventionalized Schadenfreude.
History of the two gloats. This seems to be quite murky, and tracking phrase origins and histories is not my thing, so for the moment, this 10/27/08 posting from the Phrase Finder site is the best I can dredge up:
[query from reader:] Does anyone know the origin of the phrase “how do you like them apples?”. I saw (or rather heard) the phrase in the movie ‘Good Will Hunting’ and while I understood the sentiment that was conveyed, the actual meaning eluded me…
(#3) Clip from Good Will Hunting
[Phrase Finder response:] I cannot find an authoritative source, but various sites on the web have it that the original “apple” was a mortar-fired bomb used during WW I…
The 1959 Howard Hawks film “Rio Bravo” is said to have a scene where the character “Stumpy” (played by Walter Brennan) lobs a stick of dynamite and says the phrase in question.
This came up before — also from someone watching Good Will Hunting. All I could find was that the phrase has been used since the 1920s.
[Added 8/7/19: See the comments section for some explorations into the history, in which the catchphrases appear to have their root in them apples being used as a conventional example of grammatical error (because of determiner them).]
Demotic American. Putting aside phenomena of casual speech that are widespread for English speakers generally, there are tons of sociolectal features, features distributed in particular varieties of English according to region, social class, sex, race/ethnicity, age, and so on — and then some features that are widespread for North American working class speakers, tending to run across region and other social factors. A brief inventory of some of these:
negative concord (aka multiple negation): I didn’t see nobody nowhere
specific verb forms: PRS 3 sg don’t (She don’t like it); PRS 1 sg says (So I says to them...); PST seen (I seen them do it), done (She done it); auxiliary verb ain’t
PSP identical to PST: I have ran
anyways for standard anyway
pronouns: determiner them (for deictic those); AccConjSubj (Him and me went together)
A working class speaker won’t necessarily have all of these, but there’s a strong tendency for them to co-occur.