[jkaplowitz]

Well, Houston St in New York is actually named after a person who called pronounced it "House-ton", not after the same Sam Houston as Houston, TX. This was the street's namesake, using an alternate spelling of the last name (spelling was in general less standardized back then):

https://en.wikipedia.org/wiki/William_Houstoun_(lawyer)

So, no joke involved in that case.

[balnaphone]

Note for Brits and Canadians: "house-ton" is not how you pronounce Houston St in New York, it's "how-stun" (IPA /ˈhaʊstən/). In constrast, Houston TX sounds like "hew-stun" run together (IPA /ˈhjuːstən/).

[jkaplowitz]

Ah right, wasn't thinking of the Canadian "ou" diphthong or British vowels. Thanks for adding the IPA.