North American X-15 NASA/USAF Rocket Plane Project got a test plane to 67 miles in altitude and got all program pilots astronaut status who exceeded 50 miles. The Space Shuttle Program was made possible by data collected by The X-15.
The Tupolev Tu-95 is a large, four-engine turboprop-powered strategic bomber and missile platform. First flown in 1952, the Tu-95 entered service with the Soviet Union in 1956 and is expected to serve the Russian Air Force until at least 2040. Wikipedia