Without looking too hard -
1956. The Tu-104 makes its debut as the world's first commercial jetliner.
1965. Mil's Mi-12/V-12 makes its maden flight. It is still the largest helicopter ever build.
1968 (December 31). First flight of the Tu-144, the world's first supersonic transport.
1988 (November 30). Rollout of the An-225, the world's largest airplane.