My #1 vote for pilot is Chuck Yeager. Not only an amazing pilot, but an all around good guy.
As far as planes. Depends on the catagory.
A WW2 fighter would be the P47. Big, ugly and tough.
The P61 Black Widow looked like it would have been great fun to fly!
Jet fighter, F4. Big ugly and tough. (seems to be a pattern)
WW2 bomber would have to be the B26 Marauder! In the hands of skilled pilots it was a great machine!
Jet bomber, might be the B58. When the wings stayed on, what a ride that must have been!
For jets I have flown, I just love the Dassault Falcon 50. One of the smoothest rides around. A true pilots aircraft. And a damn nice looking machine too. The Citation X is great fun too. Something to be said about having a max alt of 51,000 feet and a cruising speed of .92 Mach!