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Six definitive songs: The ultimate beginner’s guide to Tom Petty

The late, great Tom Petty had a career like nobody else. After making his emphatic arrival in 1976 with his mindblowing debut LP Tom Petty and The Heartbreakers, over the next 40 years he would carve out a niche for himself that is incomparable to anybody else. Despite being recognised as one of the greatest American songwriters of all time, he always operated from the outside looking in, expertly crafting mainstream hits from the periphery.

With the genre of rock music struggling to hold the same gravitas it once did, we are doing our bit to help educate our readers on some of the genre’s greatest ever artists and, perhaps most importantly, their foundational figures. While some of these acts are rightly known as icons, we’re a little concerned that they will remain just that—icons. For us, the real pleasure of such stars is the art they created so we are handing out a crash course in some of music’s finest, this time we’re bringing you the six definitive songs of Tom Petty.

Like many of his counterparts, Petty had a distinct sound, one which he had honed to a tee and made the call to stick to a sonic structure rather than experiment with each album as stars like Dylan and Springsteen had. Many have tried to follow in Petty’s footsteps but nobody has quite nailed Americana in the same way that he mastered it and nobody probably ever will. Don’t worry if you find the back catalogue of Petty too daunting to get stuck into and don’t know where to start, this feature has you covered.

The Heartbreakers were born to rally against “disco trance music,” according to Petty, and produce “the kind of rock that used to come blasting out of the AM radio when every song was a new Creedence or a new [Rolling] Stones, and all you wanted to do was crank it up.” That’s exactly what Petty set out to do and if you turn on AM radio even in 2020, chances are you won’t be waiting too long before a song by The Heartbreakers comes thundering across the airwaves.

Across sixteen LPs, Petty and his band the Heartbreakers delivered some of rock’s defining moments and the noodling story of Americana. It ranks as some of the most comprehensive and yet understated work you could ever come across. There is too much goodness to know where to start with Tom Petty, so here is a selection of songs which define the artist.

Six definitive songs of Tom Petty

‘American Girl’ (1976)

The only place to start on this list is with ‘American Girl’. If this euphoric beauty doesn’t seduce you into the grasp of Tom Petty then, quite frankly, nothing will. The song is an undisputed specimen of electrifying joy, one which shows exactly what kind of songwriter Petty was — it could quite easily be christened as the alternative national anthem of America. Despite the track nor the album becoming a commercial hit, both would become fan favourites with Petty’s audience over the years.

Tom Petty once said of this song: “I wrote that in a little apartment I had in Encino. It was right next to the freeway and the cars sometimes sounded like waves from the ocean, which is why there’s the line about the waves crashing on the beach. The words just came tumbling out very quickly — and it was the start of writing about people who are longing for something else in life, something better than they have.”

‘Don’t Do Me Like That’ (1979)

‘Don’t Do Me Like That’ was the lead single taken from Petty’s stunning third album Damn Torpedos and is the sound of a musician at the absolute peak of their powers. Everything he touched at this point was turning to gold and you can hear this exuberance bleed into the dancey bounce of ‘Don’t Do Me Like That’.

There’s not a wasted second in this song, The Heartbreakers made sure to carry no fat which makes the listening experience an unstoppable exhilarating ride. The track may not lyrically be the deepest in the world but it’s a fun bop nonetheless and, if you’re looking for deep, there’s plenty of other singers bidding for your attention. Petty had originally written five years before in 1974 when he was still in Mudcrutch but hung on to it for another five years before finally finding a home for it on Damn Torpedos.

‘Free Fallin’ (1989)

Tom Petty made the boldest call of his career in 1989 when he cut The Heartbreakers from his upcoming project. Instead, he opted to unleash his first solo album which proved that he could operate just as wonderfully on his own two feet as he could with a group. Full Moon Fever is arguably one of the defining rock albums of the decade and ‘Free Fallin’ is one of the finest tracks that Petty has ever written.

This era re-established Petty as a star once again after some years spent treading water, this break from The Heartbreakers was exactly what he needed. The album was produced by ELO’s Jeff Lynne, who also co-wrote ‘Free Fallin” and this opportunity to create with new people was one that reinvigorated Petty’s artistic outlook.

In a 2006 interview with Esquire, Petty stated: “‘Free Fallin” is a very good song. Maybe it would be one of my favourites if it hadn’t become this huge anthem. But I’m grateful that people like it.”

‘Wildflowers’ (1994)

Shortly after Petty became a huge solo star, he reconvened with his bandmates for 1991’s The Great Wide Open. He then laced up his solo boots once more to produce arguably the record of his career. The title track acts as the perfect opener to 1994’s Wildflowers. It is a gorgeous warm folk song which is quite the deviation from the full-throttle, driving-rock that he had mastered with The Heartbreakers.

Producer Rick Rubin managed to unlock that extra special something out of Petty for this record and allow the singer-songwriter to showcase a different side to him. “I just took a deep breath and it came out,” Petty later said on writing the masterpiece. “The whole song. Stream of consciousness: words, music, chords. Finished it. I mean, I just played it into a tape recorder and I played the whole song and I never played it again.

“I actually only spent three and a half minutes on that whole song. So I’d come back for days playing that tape, thinking there must be something wrong here because this just came too easy. And then I realized that there’s probably nothing wrong at all.”

‘The Last DJ’ (2002)

‘The Last DJ’ is an exemplary piece of songwriting by Petty. By this point in his career, he had witnessed everything in the world change before his eyes and almost nothing apart from him had remained the same. Petty sings in the voice of a fan of a local radio DJ who is planning to move from Florida to Mexico in a search for freedom as they can no longer play the songs they wish to on the airwaves.

However, the song is much deeper than that. It can be related to Petty, who was now considered a veteran in the world of music and felt like an analogue man in a digital age. Petty later told Mojo that in the song, “Radio was just a metaphor. ‘The Last DJ’ was really about losing our moral compass, our moral centre.” The correlation between the DJ and Petty’s jadedness added further weight to the song.

‘American Dream Plan B’ (2014)

Petty’s final record came in the shape of 2014’s Hypnotic Eyes, which was a return to form by The Heartbreakers. Although it was an utter tragedy that this would be the last time they would cook up a record before Petty passed away, at least his final work was up there with his best. The record is one hell of a defiant way to bow out and ‘American Dream Plan B’ is the finest song they created in the 21st Century — proving that class is permanent.

The song tells the tale of how the American Dream has slowly fallen through and sees the protagonist begging to have a shot at happiness despite the difficulties that face their generation. “The economy crashed because, aside from some very crooked people, you had Americans believing they could live way beyond what they could afford through loans,” Petty said about the song. “The guy in this song has decided to dream big because there’s nothing left for him to do. He has nothing.”

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