When I was on the college newspaper staff, I had a staff member who was a big music buff, and he had a Tom Petty greatest hits album. I borrowed it to burn onto my computer. He later asked if I still had it. I told him I did not. He wondered who did, then quoted an obscure Simpsons joke that made me chuckle: "Talk about 'petty' theft!" About a year later, I realized I actually did still have the album. Oops.
I had a friend who was feeling sad and wanted to listen to sad music. She was big into emo and was telling me that it was too depressing for her. I suggested some "upbeat sad music," as if that's a genre. I asked if she knew who Tom Petty was. She wasn't familiar with his work. I told her to look up "You Don't Know How It Feels." And that's how she became a fan.
Here, quickly, I'll throw out a rough "Top 10" favorite songs of his.
"Into The Great Wide Open" ... A tale of a couple moving to Hollywood and becoming huge music stars, only to turn bitter at the success they encounter.
"Mary Jane's Last Dance" ... There's a reason why every cover band plays this one. It's a great song that everybody knows the words to and enjoys.
"You Wreck Me" ... Something about the line "I'll be the boy in the corduroy pants, you be the girl at the high school dance" has always resonated with me. There's a nervousness and anxiousness in this track.
"Free Falling" ... Such a nice song about being an asshole to a sweet, innocent girl. "I'm a bad boy, cause I don't even miss her. I'm a bad boy, for breaking her heart."
"Walls (03)" ... There are a couple different versions of this song; one is more upbeat and slower, for a movie soundtrack. This version isn't necessarily "harder" or "louder," but it's a little less pop-sounding.
"Learning To Fly" ... Another song about life and the hardships contained within. Sometimes you have to do things before you're ready -- "learning to fly, but I ain't got wings."
"Stop Draggin' My Heart Around" ... Technically, a Stevie Nicks song featuring Tom Petty, but it's great. It's a tale of two lovers singing back and forth to each other, about how they need to figure out what they're doing.
"American Girl" ... A story of optimism; a girl going off in search of what she believes is her American dream.
"Even The Losers" ... Another tale of optimism, as even the losers get lucky sometimes.
"The Last DJ" ... One of the later tracks Petty released, this one is an angry take on the state of the radio industry in the early 2000's.
We'll close with his 2004 tribute to George Harrison. Prince stole the show, but everybody rocked out hard.