As a teenager in the late 1990s, I learned a hard truth about music: Your album collection couldn’t, and shouldn’t, be taken seriously without a copy of Tom Petty’s Greatest Hits. That’s why I went to the Tower Records on 4th Avenue in New York City one afternoon in ninth grade to cop the album, with its maroon cover and purple CD. Of all the records in Petty’s discography it’s by far his best selling, a perfect record for road trips, cookouts, and everything in between.

Throughout his career, Petty’s songs cut to the core of human emotion. His catalogue expressed an everyman bent, one that was shared by anyone who came in contact with his music, which was everyone. Petty and his Heartbreakers were a classic rock mainstay from the moment the first album dropped in 1976. His singles ran the gamut from love to heartbreak, depression to longing. “American Girl,” “Don’t Do Me Like That,” “You Got Lucky,” “Free Fallin‘,” these were songs meant to be sung off pitch and in unison. How else could you know the classics if you didn’t own the one album that had them all?

After a day of conflicting reports, Petty passed away at the age of 66 after suffering cardiac arrest. Petty the musician seemed to have an easy going nature that, when coupled with his light Southern drawl, made him an indispensable companion. As Bob Dylan told Rolling Stone upon hearing of Petty’s death, “It’s shocking, crushing news. I thought the world of Tom. He was great performer, full of the light, a friend, and I’ll never forget him.”

Petty always seemed to be more of a friend to his fans than a distant celebrity. Each song felt as if it was being sung directly for you, and there was an instantaneous connection whenever you heard your first Petty song. Rob Harvilla of The Ringer writes of singing Petty’s “Alright For Now” the first time he held his newborn son, and a quick scan of social media reveals musician’s impact to casual fans and diehards alike.

Despite buying his Greatest Hits album, I never quite bonded with Petty like others have. Sure, I could karaoke his discography with the most ardent of his fans, but Petty always felt a bit too sentimental, a bit too middle of the road. It wasn’t until my own son was born this past spring that I discovered a newfound appreciation for Petty. My wife and I have a playlist of five songs that we play during our son’s feeding, and the second track is Petty’s “Wildflowers,” which was produced by Rick Rubin and is off his second solo album. The song is a simple tune — an acoustic guitar, some maracas — with a message describing a amicable separation.

But the more nights I sing this song, I realize Wildflowers has nothing to do with a peaceful breakup, or even a relationship. It’s about wanting the best for someone that you unconditionally love. Regardless of their decisions, you’ll support whatever choices they’ll make because of how much you trust and love that person. At least, that’s what “Wildflowers” means to me; like any good Petty song, it will likely mean something entirely different to someone else, and that underscores the brilliance of his music. It’s omnipresent, but never boring.

Steven Hyden analyzed Petty’s career arc for Grantland in 2014, with a special emphasis on how his relationship with the musician changed over time:

So, for real: Who is Tom Petty? He has always been an aloof presence in his music. He’s like the stoner Clint Eastwood, wielding a crooked smile like a long-barreled hand cannon to prevent any too-close attachments. He’s a hard guy to get a read on, particularly in the last 20 years, when he receded from pop culture and became an eternally cranky and fitfully insightful recluse. And yet, again, his music is still there. It’s summertime, and Tom Petty songs are playing in baseball stadiums, across outdoor bar patios, and inside cars embarking on cross-country road trips. He’s always with us even when he’s not present….

…I’m not saying Petty’s music is itself superficial or devoid of emotion, just that tapping into Petty’s emotional core isn’t essential to enjoying Full Moon Fever. For most people this record is merely a tuneful amalgam of easy chords and easier smiles. Then 25 years pass, and Full Moon Fever is woven into the fabric of your life, and “Free Fallin’” somehow turns into a song about you. Petty has a lot of songs like that. He works the long game.

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