The fist pilot to be cerified in the USA was Charles Lester ("Les") Morris. He was certified as a commercial pilot on the Vought-Sikorsky VS-300 helicopter by the CAA (now FAA).

The second pilot to be certied was Igor Sikorsky, followed by Floyd Carlson of Bell.

Source: "The Development of U.S. FAA/CAA", J.H. Major, VERTIFLITE May/June 1984, Page 119