A recent question on EL&U asks Is it correct to use "how's" as short for "how does"? I have a series of tangentially related questions about a fairly common (in American English) phrase usually spelled as "how's about":
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Does the spelling "how's about" make sense under normal conventions of punctuation, and (if so) is the "how's" component of the phrase a contraction or a possessive?
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If "how's" is a contraction here, what words is it a contraction of?
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If "how's" is a possessive here, how might we restate the underlying idea to indicate the possessive aspect of how, without including the apostrophe-s?
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If the spelling "how's about" (with an apostrophe) doesn't make complete sense, is there a better way to spell it?
By way of background, I note that Robert L. Chapman & Barbara Ann Kipfer, Dictionary of American Slang, Third Edition (1996) offer the following entry on "how's about":
how's about prep phr by 1925 What do you feel or think about: How's about a drink? —Budd Schulberg
The first edition of this dictionary (1961) reported that "how's about" means "how about," suggesting that the apostrophe-s is simply an instance of proparalepsis (adding an extra syllable or letters to the end of a word). But even if we attribute the additional sound to proparalepsis, we have not yet explained why orthographically the spelling came out as "how's."
Not surprisingly, an Ngram Viewer graph of Google Books content shows "how's about" as being generally far more common than "hows about," "howsabout," and "howzabout"—three possible alternative spellings.
Best Answer
Early 'how's about'
The earliest instance of the expression, in any form, that I could find in Google Books and Elephind newspaper database search results is from Bob Russak, "The Art of Plugging," in the New York Clipper (December 19, 1914):
The Clipper was not a regular daily or weekly newspaper; rather, it was a weekly that billed itself as "The Oldest American Theatrical Journal."
The next Elephind match is considerably later and appears in an editorial headline of a newspaper far from New York City. From "How's About Weihaiwei," in the [Honolulu, Hawaii] Daily Nippu Jiji (June 5, 1923):
There is enough of an echo of the editorial headline "How's About Weihaiwei" in the subsequent question "How is it with Weihaiwei?" to suggest that the editorial writer sees "How's" in the headline as a contraction of "How is it," with a meaning along the lines of "What's going on." It is rather more difficult to draw the same conclusion about the usage of "how's about" in the New York Clipper article from 1914, however.
And then, from "Hawaii's Young People in Old Capital Go Mushroom Hunting," in the [Honolulu, Hawaii] Daily Nippu Jiji (November 9, 1927):
Then back to New York, in a Hathi Trust search that yields this entry in Library of Congress Copyright Office, Catalogue of Copyright Entries, Part 1, Group 3 Dramatic Compositions [and] Motion Pictures, volume 1, number 1 (1928):
Early 'howsabout'
From Ted Sokol, "Personal Piffles" in the [Cleveland, Ohio] Case Tech (January 14, 1932):
From an unidentified article in Motion Picture, volume 47 (1934):
Early 'howzabout'
From J.R. Allen, "Loco Weeds," in the [Cleveland, Ohio] Case Tech (April 21, 1932):
From an unidentified item in The Film Daily Year Book of Motion Pictures (1935):
And from an untitled item in the [Bloomington, Indiana] Bored Walk (February 1936) [combined snippets]:
Early 'hows about'
The earliest Elephind match for the spelling "hows about" (with no hyphen) is from Aunt Haru, "Pins! Pins! Pins!" in the [San Francisco, California] Shin Sekai Nichi Nichi Shinbun (September 23, 1933):
But just two weeks later the same newspaper uses the spelling "how's about." From "The Club Hamanoya....: Intimate Impressions of Lil Tokyo Night Club," in the [San Francisco, California] Shin Sekai Nichi Nichi Shinbun (October 6, 1933):
Early 'howz about'
From "Rummagings," in the [Santa Rosa, California] Oak Leaf (September 22, 1933):
From "Arithmetic," in International Stereotypers' and Electrotypers' Union Journal (1934) [combined snippets):
Early 'how'sabout'
From Bill Van Dusen, "Sidelights from the Sidelines," in the [Santa Monica, California] Corsair (January 9, 1935):
Assessment
The earliest form of "how's about" that I could find is the one with the apostrophe in place and the word rendered as two words. The earliest instance (by a fairly wide margin) is from a New York thetrical paper in 1914; then come instances from Hawaii in 1923 and 1927, and then another New York instance from 1928. Alternative spellings begin to appear in 1932—the year when the expression seems to break out of its localized popularity and spread across the United States.
It would be hard to identify two U.S. locales significantly more distant from each other than New York City and Honolulu, and I consider it somewhat more likely that the expression arose independently in the two places than that a New Yorker carried it across the cintinent and half th Pacific Ocean to Hawaii, where it took root like an invasive species. But that is a possibility.
What the two locales had in common in the first quarter of the twentieth century was a high percentage of non-native English speakers. It is thus possible that "how's about" emerged in both place by analogy to other English expressions. For instance, Elephind returns matches for "How's tricks" from as early as 1873.
Another expression that seems syntactically tangled in a somewhat similar way is "how's by you?" Leo Rosten, Hooray for Yiddish (1982) claims that this expression originated as "Yinglish" (his word for a hybrid of English and Yiddish"), but the earliest instance of it in a Google Books earch is from 1928, so it doesn't have a good chronologial claim to be an inspiration for "how's about."
But whether adding a "z" sound to "how about" is a natural thing for some non-native English speakers to do to make the phrase easier for them to say is a separate issue from the question of why a writer, seeking to represent the sound of "howzabout" on paper would resort to adding a hyphen to "hows." The answer in that case may simply be that doing so makes the speling look more normal, even though the "how's" in "how's about" doesn't have any obvious logical connection to "how is" or "how was" or "how does."