This is a tough one for me. I think some of the best food I've had has been at hole-in-the-wall places.
Mine would probably be at the Palm in Puerto Rico: prime rib, creamed spinach, chocolate cake. Not ridiculously priced, but probably $90ish.
As a missionary at a basic Brazillian rodizio where I probably gained 10 lbs. I had at least 7 fried bananas and drank multiple Guaranas in addition to meat.