We can of course carry this a little further...
Who was the first US president to be a licensed pilot, and regularly fly Air Force One...(altho it might not have been called AF1 at that time)?
And, by 'fly', I mean actually fly the aircraft (including takeoff and landing), not just riding along in a pilots' seat.
Keep in mind that AirForce One is not necessarily the big four engine piston/jet either.