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Tom Petty shouldn't have been huge in 1989. 1989 was the time of Bobby Brown, Paula Abdul, and Guns n Roses. Petty was nearly 40 years old, and roots tinged rock and roll wasn't exactly lighting up the charts. But that's what has always been cool about Tom Petty: He was always just there, doing his own thing. While other "classic rock" artists have had comeback hits, Petty just had hits. Virtually from the start of MTV to when they stopped showing videos, he had massive hit videos for decades.
Petty never went through a grunge phase. He never dabbled in industrial, or released an electronica record. He just made the records he wanted to make, and that's what made him so effortlessly cool. He released what might have been his finest album, Wildflowers, in 1994, 18 years since the first Heartbreakers album was released. In the mid 1990's, literally everything was considered alternative. Sheryl Crow and Jewel had the alternative label thrown on them at some point. You know who wasn't alternative? Tom Petty. "You Don't Know How it Feels" was a huge song back in the days of Dr. Dre and Bush. How cool was Tom Petty? The video was censored by MTV, the station of cool and youth, for saying the word "joint."
Tom Petty's music is timeless. It truly is. He's never released a bad album. (If you say The Last DJ, you're wrong. Listen to that one now that rock radio is effectively dead, and tell me it isn't brilliant.) You don't know anyone who doesn't like Tom Petty. Ok, maybe you have a cousin that only listens to black metal or hardcore, but if you listen to more than one genre of music, Tom Petty is your guy. And he has been for years. Comedians Jonah Ray and Marc Maron both have jokes about Tom Petty being the one thing that can unite all Americans since he's the one thing we all like. And now he's gone. And we're going to have to figure it all out without him.