Cold War Face Off "Bear" escorted by an Phantom. You have to have a little sympathy for those poor guys in that loud bomber. The props counter rotated with tips that exceeded mach 1 so eight shockwaves beat on the crew all flight long.
Ekranoplan Casspian The Russian Tank-Ship-Plane. Not exactly a plane but still cool. It flies just over the water because of ground effect. So it can haul a heavy load very efficiently compared to getting it up to altitude. Or floating.
Curtiss Warhawk - the plane renowned for it's duty flights in China with the Flying Tigers squadron. The Warhawk was used by most Allied powers during World War II, and remained in frontline service until the end of the war.
McDonnell Douglas Phantom II - though I worked on some of the systems in the (spy bird). Proof that with enough power, even a brick will fly. (though I've been told that the hydraulic flight control system takes some getting used too)