Since Tom Petty’s untimely death a few months back, I’ve gone back and listened to a lot of his stuff. All of it, really. It takes a while to digest that many songs, but I started to notice patterns and tropes and themes. He’s always enjoyed telling stories in his songs, and he populates the lyrics with characters who are flawed and funny and all-too-human. Let’s take a quick spin through some of it, shall we?

First and foremost, Tom Petty characters are very flawed. Narrators are open about their foibles — the guy in “The Waiting” openly admits, “Yeah, I might’a chased a couple women around/All it ever got me was down,” while the narrator of “Don’t Do Me Like That” receives a warning from his friend: “Then he said, ‘You better watch your step/Or you’re gonna get hurt yourself/Someone’s gonna tell you a lie/Cut you down to size,” clearly implying the narrator thinks far too much of himself and his abilities with the ladies, but even he won’t be immune when a woman far more clever and uncaring than he rolls around.

We can especially see the flaws when Petty tells a story. In “Something Big,” the main character — known as Speedball — checks into a hotel while he works on…well, something big, just like the title says. There’s no indication of what that something is — it’s implied to be less-than-completely-legal and probably along the lines of a get rich quick scheme — or what, exactly, Speedball is doing to hit that something big, but he’s definitely working on it…until he simply disappears. As the maids clean his room, one of them wonders who he was and what he was doing. Her coworker dismisses Speedball as just another guy “workin’ on something big,” and leaves it at that.

There’s a world-weariness to a lot of Petty’s characters. Even the ones who start out optimistic and full of hope — Eddie in “Into the Great Wide Open,” for instance — end up getting chewed up by the machinery of life and left cynical and apathetic. We see it clearly with Eddie: the youthful optimism as he moves out to Hollywood, gets a tattoo, and learns to play the guitar from his girlfriend, which all gives way to increasing disconnect from his roots as he becomes a big deal and gets a “leather jacket” with “chains that would jingle,” while his A&R representative starts to chide him for not creating a radio single. Eddie, like so many other Petty characters, has the optimism and naivete worn out of him. His wide-eyed enthusiasm for being a big star is ground down to a weary apathy by the end of the song.

Petty himself was no stranger to the corporate cogs that ground down the likes of Eddie or the nameless rocker from “Money Becomes King” (who might well have been Eddie himself). His famous fight with his record company over album pricing, his resistance to the corporatization of rock and roll and radio, his insistence on retreating from the big shiny pop of Full Moon Fever and Into the Great Wide Open by following it up with the stripped-down Wildflowers…Tom Petty always did things the way he wanted to do them, the torpedoes be damned.

And despite it all — despite the cynicism and world-weariness in his characters, despite the victory of corporations over people so many times, despite the dehumanizing effect of so much of modern society — Petty always seemed kind of hopeful. He was a guy who truly believed in the power of music, especially rock and roll. While The Last DJ is by no means a good album (despite what my brother keeps insisting), the title track does send a thrill down the spine and remind you of the redemptive, almost religious power of music. Find the right song, sing the right words, and you can free the mind, body, and spirit. “Even the losers get lucky sometime,” he sang. “You can stand me up at the gates of Hell but I’ll/Stand my ground/And I won’t back down.” He may have sung songs about the downtrodden and the weary, about folks down on their luck and out on their asses, but he did it with a wry grin and the belief that you could recover from failure. It’s explicit in songs like “Climb That Hill,” with its admonition to “Get up/Climb that hill again.”

Back when Wildflowers came out, I listened to the album obsessively. It came out in 1994, when I was fourteen and the perfect age to obsessively listen to something. At the time, my least-favorite song on the album was the closer, “Wake Up Time.” It was slow, meditative, and not what a 14-year-old who wasn’t quite convinced of his own mortality yet really wanted to listen to. The album was, if I’m honest, too mature for me. I wasn’t ready for it. But that just means I’ve gone from giggling about the line about rolling a joint in “You Don’t Know How it Feels” to really, truly appreciating how heartbreakingly beautiful some of these songs truly are. I’ve been given a blessing, in a way: the opportunity to grow up with this amazing piece of music, to gain new insight and understanding into its songs as I’ve grown older and (hopefully) wiser. And now, I’m better able to appreciate “Wake Up Time.” The first half of the last verse goes like so:

Well, if he gets lucky, a boy finds a girl
To help him to shoulder the pain in this world
And if you follow your feelings
And you follow your dreams
You might find the forest there in the trees

Wildflowers is a sad album, a lot of the time. It’s one of those divorce records that so many artists have made over the years (Dylan’s Blood on the Tracks, Beck’s Sea Change, & etc.). But, like so much else that he did, Petty couldn’t help but slip a bit of hope in there. Things are falling apart, yes, but there’s a chance you can put yourself back together afterwards. Not all is lost. And, ultimately, I think that’s the legacy of Petty’s songwriting: he was a guy who told stories that gave us hope. What better legacy could there be?