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5 Greatest Songs by Tom Petty and the Heartbreakers

5 Greatest Songs by Tom Petty and the Heartbreakers

Few rock and rollers are as beloved as Tom Petty. This singer-songwriter and his band, the Heartbreakers, left their mark on roots and heartland rock. Even if you don’t own one of the band’s albums, you probably know at least one of their songs by heart. 

It would be impossible to choose the top greatest song from this iconic group. So instead, we decided to explore five tracks by Tom Petty and the Heartbreakers.

Join us as we discover more about these classic rock legends.

Let’s hit it!

About Tom Petty and the Heartbreakers

Tom Petty and the Heartbreakers formed in 1976 in Gainesville, Florida. Their self-titled first album, released in 1976, was a hit in Great Britain despite its limited success in the U.S. However, two years later, their second album made the American Top 40 music chart.

Their 1979 release, Damn the Torpedoes, became the band’s first platinum album. It included hits like Don’t Do Me Like That and Here Comes My Girl. The album also brought them into the mainstream. In the decades to come, Petty and the Heartbreakers collaborated with stars like Bob Dylan, Stevie Nicks, and the Traveling Wilburys supergroup.

The group received a star on the Hollywood Walk of Fame in 1999. And three years later, they were inducted into the Rock and Roll Hall of Fame. In addition, the band celebrated its 40th anniversary with a nationwide tour shortly before Petty’s death in 2017.

Tom Petty and the Heartbreakers’ rootsy, sometimes gritty aesthetic remains unmatched. And their singular sound earned them fans across genres and decades.

Let’s take a deep dive into five of the band’s most famous songs.

#1 Learning to Fly

About the Song: Learning to Fly was released in 1991 and became one of the band’s longest-running hit singles. The song spent six weeks in the #1 spot on Billboard’s Mainstream Rock Tracks chart. Petty co-wrote the tune with Jeff Lynne, the frontman for Electric Light Orchestra and Petty’s Traveling Wilburys bandmate.

Though some speculated that the song was about drugs, Petty claimed otherwise. The musician was inspired after seeing a TV interview with a pilot. In the interview, the pilot explained that landing–or “coming down”–was quite literally the toughest part of flying.

But the song took on a more profound significance too. Petty’s flight metaphor became a reference to political events of the time, including the Gulf War. In a conversation with Billboard, the songwriter described the track as “a redemptive song, only in the vaguest way.”

Greatest Lyric

I'm learning to fly
but I ain't got wings
Coming down is the hardest thing

First Appearance: Learning to Fly appeared in 1991 on Into the Great Wide Open, the Heartbreakers’ eighth studio album. It was the first single from the record.

#2 Walls

About the Song: Walls is a Tom Petty fan favorite. Its quiet, hopeful sound is a peaceful departure from many of the Heartbreakers’ up-tempo tracks. The song also marked a difficult period in Petty’s life: the songwriter was in the midst of a divorce from his first wife, Jane.

Because Walls was originally written for a movie soundtrack, there are two versions of the song. The most popular version is Walls (Circus), which features vocals by Lindsey Buckingham of Fleetwood Mac. Walls (No. 3) is a stripped-down variation on the original.

The music video for Walls, which starred Jennifer Aniston and Edward Burns, was a hit. Set in a psychedelic circus, it features technicolor animals and rooms bursting with flowers. Phil Joanou directed the six-minute video.

Greatest Lyric

Baby you got a heart so big
It could crush this town
And I can't hold out forever
Even walls fall down

First Appearance: Walls appears on the soundtrack for the film She’s the One, which came out in 1996. The soundtrack consisted of Petty’s original songs and score.

#3 Mary Jane’s Last Dance

About the Song: Mary Jane’s Last Dance is one of the Heartbreakers’ best-known songs. Although Petty never disclosed the song’s intended meaning, there are a couple of fan theories. Some speculate that Mary Jane refers to the songwriter’s first wife, while others suggest the name is a drug reference.

The song inspired one of Petty’s stranger music videos. The songwriter stars as a mortician who kidnaps and dances with a corpse, played by actress Kim Basinger. But the video’s unsettling themes didn’t keep it from becoming popular. In fact, it received Best Male Video at MTV’s Video Music Awards that year.

The Red Hot Chili Peppers faced backlash over their 2006 song Dani California, which resembles Mary Jane’s Last Dance. But the band wasn’t concerned. Despite the similarities, Petty and the Heartbreakers didn’t consider Dani California plagiarism.

Greatest Lyric

Last dance with Mary Jane
One more time to kill the pain
I feel summer creepin' in 
And I'm tired of this town again

First Appearance: Mary Jane’s Last Dance debuted on the Heartbreakers’ Greatest Hits album in 1993. It reached the #14 spot on Billboard’s Hot 100 that year.

#4 American Girl

About the Song: Petty wrote American Girl while living in an apartment near a highway in Encino, California. The songwriter said the traffic noise sounded like the ocean, which inspired a line about waves on the beach. The rest of the song came together quickly.

American Girl gained popularity in the U.K. before catching on in the U.S. This was one of the reasons the band started their first major tour overseas. Decades later, American Girl is still a popular choice for Fourth of July celebrations and other patriotic occasions.

This song was the last one Petty ever performed. The band ended their 2017 tour at the Hollywood Bowl and closed the set with the tune. Unfortunately, Petty died a week later due to cardiac arrest.

Greatest Lyric

Well, she was an American girl
Raised on promises
She couldn't help thinkin' that there
Was a little more to life somewhere else

First Appearance: American Girl appears on Tom Petty and the Heartbreakers’ first self-titled album, released in 1976. 

#5 The Waiting

About the Song: The Waiting takes its inspiration from Janis Joplin, who once remarked, “I love being onstage and everything else is just waiting.” According to Petty, the song is about how it feels to wait for your dreams to come true. The songwriter said he wrote the chorus quickly but struggled with the rest for some time.

While working on this record, Petty was at odds with the band’s record label, Backstreet. The Heartbreakers were so popular that Backstreet wanted to raise the album’s price. Petty refused, even threatening to name the album $8.98.

Since its release, The Waiting has appeared in pop culture dozens of times. Shows like The Simpsons and It’s Garry Shandling’s Show featured the song. There’s even a reference to the track in the 2019 film A Marriage Story.

Greatest Lyric:

Every day you get one more yard
You take it on faith
You take it to the heart
The waiting is the hardest part

First Appearance: The Waiting debuted on the Heartbreakers’ 1981 album Hard Promises. It was the album’s lead single, peaking at #19 on Billboard’s Hot 100.

An American Band

Tom Petty and the Heartbreakers are rock and roll royalty. And it’s hard to believe they first became popular outside of the U.S. Today, the band’s heartfelt, nostalgic sound seems as American as apple pie.

Thanks to their prolific discography, Petty and his band left their mark on music history. The Heartbreakers’ story may be over, but their songs live on.

What’s your favorite Tom Petty and the Heartbreakers song? Tell us in the comments!


Monday 3rd of April 2023

Either this was generated by AI or written by someone who isn't familiar with Tom Petty's catalog. Otherwise, Learning to Fly would never have been even in the conversation for this list, nevermind make the list. Also, the lyrics chosen to highlight were hardly the best or even most provocative of the songs. Lazy effort folks.


Monday 3rd of April 2023

No AI, simply our opinion. Thanks for commenting!

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