Wise guy and wise man.

Almost the same but very different in meanings. Can you think of more?

Well, taking it political, Tory and suppository.

Interesting observation, Angel.
I searched Word Detective, World Wide Words, Google, and the online Slang Dictionary (BTW, do you know that "word" means "yes", in slang?)--with no real insight into why the different meaning of "wise guy" and a "wise person". I did find that in Hebrew "wise" means "skilled for living life well", which of course relates to a "wise" person, but not to a "wise guy".

One of the early Dennis the Menace cartoons had Dennis running to his mother saying, "Mom, my teacher says I'm a wise guy!" His mother inquired further, and Dennis replied, "I get to be one of the three wise guys in the Christmas play!" This, probably circa 1962. Oooohhhh, am I THAT old?

To take your original premise and totally reverse it, to say someone has a "slim chance" of success while saying someone else has a "fat chance" of success, while seemingly directly opposite mean the exact same thing. They ain't gonna make it! The first phrase is to be taken literally, of course, while the second is widely understood sarcasm.

This is all part of why English has to be one of the greatest languages in the world (I'm mildly prejudiced, of course) for expressing thoughts in an arresting or interesting way. Similarly, it has always struck me as amusing that, in terms of slang, if you're skating on thin ice you may soon find yourself in hot water.

Only in English would that sentence make perfect sense.

Only one I can think of similar to your 'wise man wise guy' pair is 'evening gown and night gown'. Can you imagine showing up in one when you should be in the other?

Only one I can think of similar to your 'wise man wise guy' pair is 'evening gown and
night gown'. Can you imagine showing up in one when you should be in the other?
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Not being a transvestite, I can't imagine showing up in either! Now, showing up in the wearer is another matter alotgether!

Ahhh, Museamuse, you're finally back! Morgan and I have been struggling without you! Did you see the "wives" thread yet? Sheeesh!

Contemplating museamuse in an evening gown ...
Contemplating museamuse in a night gown ...

Difficult to concentrate on words here ... but under the circumstances, would it be too naughty of me to suggest that the word-pair intermission and intromission might fit this thread's theme?

How about:

overlook and oversee?

The two uses of "wise", serious and sarcastic, recall the dicussion of a word from yiddish, chachem = wise person.