Celebrities Take On The Sky

Alan Jackson: Country Crooner and Sky Pilot

Alan Jackson was just a simple Georgia country boy, not believing that his dreams could actually come true, not to sing or to fly. On both counts, he was wrong.

Jackson watched as some of his friends, who had dreams of becoming commercial pilots made those dreams come true, and it inspired him to do the same. “When I started flying to work, I got interested in watching [the pilot who flew me] and he taught me. At that time, we had a farm with a pretty big grass strip and I had a plane with amphibious gear, so I [could] land on water, the lake … just kind of flew around Nashville. I still have my license,” Jackson said on his personal website. Nowadays, he doesn’t fly as much, because his wife worries about him.

James Lipton: Brave Aeronaut

James Lipton is well-known as a celebrity interviewer and the executive producer, writer, and host of Bravo’s Inside the Actors Studio. Lipton has been piloting planes longer than he’s been asking Matt Damon about his personal life, however.

Lipton always wanted to fly, but couldn’t afford lessons, so he joined the military to be a fighter pilot. He’s is certified in Airplane Single Engine Land planes, and has been flying since 1980. He learned in a Cessna 152 and 172 at Van Nuys airport, and has amassed over 1,000 hours of flying time. Lipton is a member of the Aircraft Owners and Pilots Association. In a harrowing flight in 1956, Lipton flew the Aeronca Champ along Alaska’s Iditarod Trail. Lipton lost the engine in a furious snowstorm, flying through a mountain pass, but with a cool head, was able to get it restarted.