I couldn't believe Gomer Pyle was a $2,000 clue in the Military TV category, and was heartbroken when it was a TS...
I got Havana right away - New York City almost would have been the right answer, but part of it (The Bronx) is on the mainland.
It was actually "What's the difference between you and a man with a cold..." but he didn't really have a punch line.