Most I ever paid? $82 not too long ago at P.J. Clarke's. Raw oysters and clams, a lobster roll, cheesecake, and an Irish coffee. Well worth the cost, although it usually comes out to less there- like $60. I blame the fact I'd finally made it to the opera that night and the waitress was also very attractive.
Most expensive? Probably at the Capital Grille in Boston on the occasion of my cousin's graduation from MIT, last year, the steak I had was $40 or so on top of appetizers and dessert, with some 12-15 of us, and their wine considered, I'd expect it to be upwards of $2500. I might have spent more at Delmonico's on my birthday a few weeks back- I had an entree of $45 Lobster Newburg (and a rather tough one at that!) plus some oysters, bread pudding, and Madeira. Probably like $90, but I was forcibly prevented from seeing the check, much less paying.
Bedstuy, Eleven Madison Park or Per Se? (There's also a place with such prices in Brooklyn which I am neglecting and whose name I am forgetting, but who cares, it's in Brooklyn). Perhaps Daniel and Jean-Georges are contenders here.
Ultimately I am the sort of person who loves good food but would hate to pay for it- you eat and then- it is gone, just like that. And you are out $50. Which is the entry price for a great meal in this city sadly- maybe $40 but keep in mind a meal at McDonald's here is $10- and adjust your scales accordingly.
This is why the world hates America.