I have to answer this without much thought, because the more I think the more airframes I want to fly.
However, I have to start with the oldies. A F4, P51 or even a T6, and maybe throw in a b25.
A beech 18
A dc-3
now modern age, a B-757
a challenger (doesn't matter 604, 300) and a G4 or 5.
Of course modern military would be the F16, and 15