Perhaps more than anyone with his longevity in the music business, Tom Petty got the most out of his talent. The Heartbreakers started their career in an era of larger than life arena rock bands. "Larger than life" couldn't possibly be a less fitting description. Petty was an average looking rocker dude from Florida, who fronted a band of similarly average looking dudes. You could say the same about Springsteen and the E Street Band, but come on ... they had the Spectorian glamour from day one. They were always a stadium band stuck playing clubs until they got big enough. The Heartbreakers where straight ahead, nose to the grind, professional rockers. In another life (say, if Petty had been born fifteen years later), he might have had a career the likes of Jon Spencer -- essentially that of a pub rocker with a strong cult following, who occasionally sniffs major label success via short-lived collaborations with a hip producer, but always ends up retreating back to the underground. Most musicians would kill to have Jon Spencer's career, but Jon Spencer never played the Superbowl halftime show.
Forty years ago, could anyone have predicted how Petty's career would turn out? As the 70's rolled on, he timed his album releases perfectly with the rise of punk. Petty was rootsy enough to be liked by the classic rock crowd, and no frills enough to be liked by the new wave crowd. That dual cred was still sustaining him in the early 90's, when the previous generation of 70's and 80's rockers had been cleared out by the younger, filthier grunge and alternative stars, with the exception of Neil Young and Tom Petty.
At the end of the 80's, he looked out of place as the youngest Travelling Wilbury by far. Musically, he blended in just fine, and you'd be forgiven for thinking this would mark the beginning of the Stones/Who never ending nostalgia tour phase of his career. But the next year he released his most successful album, "Full Moon Fever". And a few years later, Petty's videos were in heavy rotation in MTV and remained so throughout the early and mid 90's, long after many of his earlier contemporaries were no longer considered relevant to the Gen-X and Y crowd.
Petty had a lot of great songs, but the most special one for me is "Learning To Fly", which essentially kicked off my mini-obsession with "repetitively strummed acoustic guitar" songs such as Kristin Hersh's "Me and My Charms", James' "Laid", and countless others. Plus it has one of the best "coming of age" lyrics ever written.