Technical history of VTOL aircraft is examined from the early helicopter appearance to recent experimental rotorcraft in order to distinguish the core issues of those aircraft. Performance and technological challenges of some VTOL aircraft such as tilt rotor, convertiplane, gyroplane, and coaxial helicopter are discussed. As a new generation high performance rotorcraft, Sikorsky X2 is intensively investigated. Considering the developmental history of X2, the autorotational ability at high speed is recognized as a core technology. Analytic method of autorotation and some results are shown and presents research subjects related to the future Korean high performance rotorcraft.