To me, Will Shortz is an icon's icon.
I have a friend who leans more toward the scientific than I do, so we balance each other well in terms of trivia. When we get together (he lives in California, so I don't see him often) we usually try to incorporate the Sunday NYT crossword into our activities. Last time we worked on it together, we beat our previous record of 55 minutes by 3. But I remember actually completing only one alone, with no help. Now as for those cryptic crosswords, fuhgeddaboutit. Never could understand them.