"Learning to Fly" (1991)
Into the Great Wide Open was written while Petty turned 40, which put him in an introspective mood. "I suppose I'm just working a lot of things out," he said. "It's very hard living your life as we have in tour buses and airplanes for all of this time. I think when I turned 40 I kind of did, as most people do, get a little reflective about 'Where have we been? And where are we going?'" "Learning to Fly" is about the importance of constantly trying new things and learning from one's mistakes, and the video frames that sentiment in luscious, melancholy black-and-white images, presenting us with a coming-of-age story that's utterly surreal. The video's young hero gets propositioned by an older woman, sees UFOs, and falls in love while surviving a fiery car crash. In the bizarre world of a Tom Petty video, that's just a normal adolescent tale.