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Captain Eric Melrose "Winkle" Brown, CBE, DSC, AFC, FRAeS, Royal Navy is officialy credited with flying 487 different aircraft but only includes basic types. For example Captain Brown flew several versions of the Spitfire and Seafire, and although these versions are very different they only appear once in the list. He is in the Guiness Book of World Records.
Hoot Gibson went to the same college as me. There is, or at least was when I was in the department, a big picture of him in the Aerospace Engineering department.
Several years ago (96) a bunch of us Lt's got a good deal to take a Prowler to Oshkosh for the big show. There was no contract gas there so we went to Scott AFB and got a bag full. While we were there a NASA T-38's showed up. Hoot was flying and came over to say hi. He was going to the show as well and spent 15 minutes giving us the gouge. Heck of a nice guy and very personable to be around. He came by at the jet at the show and said hi a couple times and swapped tales, his were better, much much better.