"Free Fallin'" (1989)
Petty put aside the high-concept angles for "Free Fallin'," an appropriate move for a song whose gentle melody and wistful sentiment didn't need a lot of fancy adornments. The songwriter was inspired to write the folk-ish hit by noting the scene to and from the recording studio: "I tried to grab a little bit of these characters on the road and it was kind of how I saw it," he said. "It's pretty true of that time and that era … The skateboarders and the shoppers and the young kids in the trendiest possible clothes and the auto-tellers and the drive-thru banks." The video, filmed partly at the Westside Pavilion mall in Los Angeles, brings those images to life. Petty plays a sort of omniscient observer gliding above Southern California chronicling the song's unnamed young woman (played by Devon Kidd) as she looks for love and contentment, finally finding some sense of serenity while skateboarding in slow-motion. Lots of Petty's videos are funny, but "Free Fallin'" might be his most touching.