By Air (Round 3)
Credit: Tracy A. Woodward / The Washington Post / Getty Images

Winner - Fossett: Gagarin died at 34 flying a MiG-15. Fossett died in a somewhat less ballsy aircraft, but before that day set a ridiculous list of firsts. First to round the world solo in a balloon. First to fly a plane around the globe without stopping to refuel. First glider flight into the stratosphere.