Two recent cartoons turning on fixed expressions, compounds in fact: a Rhymes With Orange and a One Big Happy:
(#1)
(#2)
working girl. #1 turns on the ambiguity of the compound working girl, in both senses ‘girl (that is, woman) who works for a living’ — in one sense with literal work; in the other, with a specialized sense of work: (from Green’s Dictionary of Slang) ‘work as a street prostitute’, attested from 1939 on (usually with a direct object denoting a place: work the clubs, work the street, work that corner, etc.).
The daughter in #1 intends the first, but the mother is inclined to hear the second, euphemistic for ‘prostitute’, for which Green’s has a pile of U.S. cites (with variants working broad, working chick, working woman), from 1928 on.
The expression is genuinely ambiguous, to the extent that a hit movie (not about a prostitute) could have the title Working Girl. From Wikipedia:
Working Girl is a 1988 romantic comedy-drama film directed by Mike Nichols and written by Kevin Wade. It tells the story of a Staten Island-raised secretary, Tess McGill (Melanie Griffith), working in the mergers and acquisitions department of a Wall Street investment bank. When her boss, Katharine Parker (Sigourney Weaver), breaks her leg skiing, Tess uses Parker’s absence and connections, including her errant beau Jack Trainer (Harrison Ford), to put forward her own idea for a merger deal.
(#3)
toothy comb. Ruthie’s version of fine-tooth(ed) comb is fairly far from the original, but we can see how to get there.
Start from the full expression. From NOAD2:
fine-tooth comb (also fine-toothed comb) a comb with narrow teeth that are close together. – [in sing.] used with reference to a very thorough search or analysis of something: you should check the small print with a fine-tooth comb.
The main sense here is largely compositional, ‘a comb with fine (that is, narrow) teeth’ (note the metaphorical teeth here), and the two variants are often alternatives: a three-floored building, a three-floor building (though some combinations are fixed: a three-masted schooner (not three-mast), a three-course dinner (not three-coursed)). So let’s disregard that variation. But the secondary, metaphorical, sense is specialized, and its connection to narrow teeth might be not at all clear to some speakers.
The way is then open to reinterpreting fine-tooth(ed) comb as fine tooth(ed)-comb, possibly with the adjective fine ‘excellent’ (or with fine ‘delicate’), but certainly with a different parsing of its parts. Some number of English speakers have done this. As I wrote in an eggcorn posting on Language Log some years ago:
fine-tooth comb > fine toothcomb. An interpretation reported to me by Gerald Gazdar in the summer of 1987, when I corrected his misapprehension as reflected in a paper he was writing.
Gerald (a noted theoretical linguist and computational linguist) had an image of a tooth comb — I think he understood it as ‘comb for teeth’ rather that ‘comb with teeth’ — and he’s far from the only person to have done so.
If you parse it this way, then tooth-comb (or tooth comb or toothcomb) is the head of the composite, and fine is a modifying adjective, hence in principle dispensable. In #2, Ruthie’s dispensed with fine, and understood toothed as an adjective, for which she offered the alternative toothy.
