“Music is probably the only real magic I have encountered in my life. There's not some trick involved with it. It's pure and it's real. It moves, it heals, it communicates and does all these incredible things.”—Tom Petty

In the documentary Runnin’ Down a Dream, Tom Petty says of his songwriting process, “I hesitate to even try and understand it for fear that it might go away.” How consciously Tom crafted his songs is impossible to say. Certain songs, including the two examined here, “Free Fallin’” and “Wildflowers,” came out quickly. The former over the course of a day; the latter, according to Petty, in less than four minutes. Moments of inspiration have an effervescence—a rough magic—that’s difficult to capture in a recording. Yet Petty, and his respective collaborators, managed to do this consistently. These two songs illustrate Tom Petty’s unique and honest craftsmanship.

“Free Fallin’”—Full Moon Fever (1989)

Great songs are timeless, but of a certain time. They enter a person’s life at a specific moment. That moment is like a birth sign; it leaves an imprint on the tune, sonically and perceptually. People who haven’t been listening to music very long or very deeply can tell, instinctively—by the style in which an artist vocalizes, by the instrumentation, by the production techniques—roughly when a song is from. If you play someone a Beatles song, they wouldn’t have to be familiar with it at all to guess “1960s.” You don’t have to be a 30-something ex-scenester to hear the AM radio–vocal sound deployed by the Strokes and immediately think of the early aughts.

So it’s worth spending a few words pinning “Free Fallin’,” the opening song on Tom Petty’s first solo album, to the late autumn of 1989, an epoch-altering season in history. “Free Fallin’” was released as a single on October 27 of that year, a bit more than a week after the Loma Prieta earthquake devastated Northern California, killing 63 people and derailing the World Series. Less than two weeks later, on November 9, citizens of East Berlin, responding to mixed messages from East German government regarding its border policies, mobbed the Berlin Wall. The soldiers manning the crossing points stood down. The Berlin Wall fell. Nearly three months later, on January 27, 1990, “Free Fallin’,” a golden, familiar-sounding folk song with a sing-along hook, peaked at no. 7 on the charts.

The fall of the Berlin Wall was only one of the events in 1989, great and small, which would eventually change the word. In February, the Soviets pulled out of Afghanistan. Pro-democracy protests in China throughout the spring resulted in the Tiananmen Square massacre that June, one day after the death of the Ayatollah Khomeini. In October, Quantum Computer Services renames its internet link and web-portal service for home users “America Online.”

Music, too, was in the midst of changes that would hit like a slow-rolling earthquake. N.W.A’s Straight Outta Compton dropped in the summer of 1988, launching the careers of Ice Cube and Dr. Dre, and ushering in stylistic changes—bass-heavy Parliament-Funkadelic samples over James Brown drum breaks; crime and weed-centric themes instead of sociopolitical messages; R&B-infused flows over old-school tag-teaming—that would take the genre to new heights of success and shift the axis of hip-hop from the East to the West Coast. By early 1990, Nirvana were working on the songs that would appear on 1991’s Nevermind, the fuzz-bomb asteroid that killed off the unwitting dinosaurs of hair metal.

“Free Fallin’” floated above those crosscurrents of ’89-90 like something from another time and place. Familiar but beguilingly weird. A comforting song, like a blanket warmed by the sun, that simultaneously evoked the strangeness of the time in subtle ways. Surely, that refrain (“And I’m free / free fallin’”) which practically begs to be belted from behind the wheel of a speeding automobile, must’ve sounded like the sonic embodiment of the right side of history. Communism was crumbling, the Ayatollah was dead, and we’re free, free fallin’. Parents liked it and their teenage kids liked it, too. At the 1989 MTV Video Music Awards, Axl Rose and Izzy Stradlin of Guns N’ Roses, then the hottest rock band in the world, sat in with Petty on “Free Fallin’,” signaling the track’s cross-generational appeal. The song was new, but already a classic. Timeless.

Produced by Jeff Lynne of ELO and the Traveling Wilburys (he also played bass and sang backing vocals on the track), “Free Fallin’” introduces itself with strummed chords on two acoustic guitars panned out wide left and right in the mix. The aural effect is one of an open landscape appearing around you. A soft synthesizer pad sighs above it all like a breeze. Petty’s music didn’t contain many stylistic nods to the times they inhabited; after all, Petty and the Heartbreakers were, at their core, a guitar-driven rock band. So it fell to the keyboards to convey a feeling of width and overhead space. The keyboard sound combines with the campfire homey-ness of the twin guitars. The effect, before the first word is sung, is a disembodied feeling that’s crucial to the song’s emotional impact.

Tom Petty’s lyrics are often said to be relatable or simple, and they are. Freedom and falling are not deep concepts. But, like most of Petty’s songs, “Free Fallin’” is deceptively complex. Petty creates a feeling of timelessness—what my colleague Rob Harvilla referred to as “classic rock in real time”—by pairing lyrical tropes with familiar musical ideas, then constantly shifting their perspectives. What, on the surface, seems like an easy-going folk-pop song is, on deeper examination, a series of interconnected vignettes which reframe the chorus in unexpected ways.

She's a good girl, loves her mama

Loves Jesus and America too

She's a good girl, crazy 'bout Elvis

Loves horses and her boyfriend too

From when is the narrator addressing us? A good girl, crazy about Elvis and America? Loves horses and her boyfriend (and definitely in that order)? The plainly-stated, unironic innocence and love of Jesus evokes the optimism of 1950s America.

Where is the narrator?

It's a long day livin' in Reseda

There's a freeway runnin' through the yard

Southern California, the San Fernando Valley. In the line “It’s a long day livin’ in Reseda,” we get our first glimpse of who’s singing to us. Decades of rock ’n’ roll history primed audiences to imagine the rock singer as young, or at least mentally young. Especially one who’s singing about boy-crazy girls. (“She was just 17, you know what I mean.”) But who would say “It’s [been] a long day”? Someone weary. Someone older than we think.

“There’s a freeway runnin’ through the yard.” The seemingly idyllic California sunniness has turned sour. Manifest Destiny has given way, quietly, to eminent domain. The system is encroaching on the narrator, as if the once unstoppable drive westward ceased at the Pacific Ocean, then turned back on itself.

And I'm a bad boy, 'cause I don't even miss her

I'm a bad boy for breakin' her heart

Now sincerity curls ever-so-slightly into a James Dean smirk. The unattainable rock star’s stereotypical pose.

Then comes the chorus:

And I'm free, free fallin'

Yeah I'm free, free fallin'

Notice that the stress is on the free, and not so much the fallin’. The song, to this point, is about a very specific definition of freedom. Freedom from being tied down by a girl and her various hobbies or by the banal complications of boring suburban life. Freedom from bullshit writ large. Standard rock song stuff.

Then the perspective shifts, and the song takes on a strange dimension.

All the vampires walkin' through the valley

Move west down Ventura Boulevard.

When are we now? “Vampires walkin’ through the valley” moving “west down Ventura Boulevard” paints an image of teen wastrels—hippies and hipsters and gutter punks. Young seekers hunting the neon-lit darkness for meaning or just a good time. The buoyancy and chasteness of late-’50s America is suddenly very far away. And listen to the bass line here. Lynne trades anchoring duties for melodicism, bounding upward, then sinking. He only does that here, under these lines. Like the wanderers on Ventura Boulevard, the music becomes rootless.

And all the bad boys are standing in the shadows

All the good girls are home with broken hearts

The focus tightens and it’s clear the narrator is observing a scene. He sees himself reflected in the bad boys, the young heartbreakers of the night world, leaning languid against storefronts and hanging out in alleys. What seemed present tense, recedes into the past. Though the above lines are sung with angelic, straight-arrow sincerity, they hit with a bitter punch.

Now when the chorus returns, free fallin’ feels like a wild emotional spiral into regret. The narrator is in the grip of something and it’s pulling him inexorably down. Something aching has been knocked loose inside of him and he’s falling. But from such a height that he can observe it as it’s happening.

I wanna glide down over Mulholland

I wanna write her name in the sky

Why write her name in the sky? Because he doesn’t know where she is. But if he writes big enough, she’d know that he was thinking of her. We get a new backing vocal, a breathy chorus of “ohhh-whoa-ohhh” that evokes the feeling of a fall from altitude.

I'm gonna free-fall out into nothin'

Gonna leave this world for awhile

He surrenders fully to a realization, to the sad, hopeless gravity of it. He gave something up because he thought it was weighing him down. Instead he lost something precious and it haunts him. When the final refrains sound, free fallin’, and freedom, has been revealed as absence, a wilderness. He’s alone, falling out into nothing.

Then the bridge—fuzzy electric guitars chug out the chords over a bare drum beat. The backing vocals re-enter, and perhaps for the first time, you notice that they’re like a mantra. The words of someone standing at the door of an airplane on the brink of their first skydive. We’re building to that last glorious Jerry Maguire–in-the-car refrain. The “ohhh-whoaaa-ohhhh” slams into the chorus and all the themes click into place, existing in the same space all at once. We’re free again. Flying, even. But it’s only an illusion because of the heights from which we fall.

“Wildflowers”—Wildflowers (1994)

Simple words and honest expressions are powerful because we so rarely express ourselves that way. It’s too scary. People go about their days pretending they aren’t lonely. Burying their longing under tasks and routine. Songs exist as a way to outsource our catharsis—as a vehicle to experience, secondhand, the bravery to be vulnerable.

Famed producer, dharma bum, and professional wrestling patron Rick Rubin produced Wildflowers. Rubin is known for a stripped-down approach—bare vocals, loud drums, and spare, unaffected instrumentation—and that style is on display as “Wildflowers” begins. “Free Fallin’” evokes wide-open spaces and the plasticity of memory. “Wildflowers” is up close and intimate; a music box.

Put on your headphones.

You belong among the wildflowers

You belong in a boat out at sea

Sail away, kill off the hours

You belong somewhere you feel free

Rubin positions Tom’s acoustic guitar and vocals right in front of you. He’s singing to you.

Run away, find you a lover

Go away somewhere all bright and new

I have seen no other

Who compares with you

Notice the way the piano comes in on this verse—high up the register, with only the right hand. As if the piano player (The Heartbreakers’ Benmont Tench) just wandered in, sat down, and is trying to feel out the chords. A small shaker keeps time.

The lyrics are selfless. The narrator wants nothing more than to tell you all the good things you deserve—love, a fresh start, respite from the world. The song is an affirmation.

The chorus returns.

You belong among the wildflowers

You belong in a boat out at sea

You belong with your love on your arm

You belong somewhere you feel free

This is a love song. Only someone who cares deeply about another person could speak this way. But notice how the narrator appears to be holding something back. The lines “Run away, find you a lover,” and “You belong with your love on your arm,” leave you with a feeling of affection, but the unrequited kind. As if he can’t say “I love you.”

The bridge brings in different textures—a small orchestral section and what sounds like a clavichord. The music opens up, a field of wildflowers.

Run away, go find a lover

Run away, let your heart be your guide

It’s worth asking again—who is this lover? Where does the narrator expect, if at all, your heart to lead you?

You deserve the deepest of cover

You belong in that home by and by

For the first time we hear a kick drum. A heartbeat. The narrator is nervous. The chorus again:

You belong among the wildflowers

You belong somewhere close to me

Far away from your trouble and worries

You belong somewhere you feel free

You belong somewhere you feel free

He comes out with it. “You belong somewhere close to me.” Love is selfless. To want something for someone else, to want them to be happy and free, loved and accepted, is selfless. What at first seemed like a benevolence and generosity (“go find a lover,” “sail away,” “run away”) is revealed as longing. The narrator wants you to follow your heart and he hopes it leads you back to him. But he saves that for that final verse. And even then he can’t say “I love you.” And what seems like a perfectly beautiful pop-folk affirmation turns into an aching instrument of longing; a great unrequited love song.

Tom Petty’s music was ubiquitous, which makes it easy to overlook. Like the North Star, his songs can still guide you home.