5 Devastatingly Sad Tom Petty Songs of Lost Love and Heartbreak

If you’re going to be labelled one of the finest songwriters, you better be able to write about lost love. After all, that’s a topic that never quite goes out of style, since just about everybody has gone through some sort of heartbreak in that department. 

Needless to say, Tom Petty is indeed one of the finest songwriters to ever put pen to paper and fingers to fret. And he did indeed come through with many incredible songs about the devastation that goes with the end of a relationship. These five sadder than sad Tom Petty songs really stand out.

1. ”Insider” (from the album Hard Promises, 1981)

This song is surrounded by some interesting trivia. Petty was asked to write a song for Stevie Nicks, and he came up with “Insider.” However, once he finished, he liked it too much to give away. Instead, Nicks got a hold of the Heartbreakers demo of “Stop Draggin’ My Heart Around” and turned it into a duet that became a hit single. Nicks ended up singing harmony on “Insider,” so everything came full circle. Petty didn’t release “Insider” as a single, perhaps sensing that it was too personal to resonate on a widespread level. The narrator bemoans that his ex has settled for a life of ease instead of fighting for true love, and Petty’s voice quivers with the injustice of it all when he sings the killer line, I’m the one you couldn’t love.

[RELATED: Top 5 Tom Petty Songs That Defined His Career]

2. “The Best of Everything” (from the album Southern Accents, 1985)

Petty had intended Southern Accents to be a concept album of sorts, but he also wanted to try for hit singles with then-current sounds. The result was an album that came out a bit disjointed, albeit with several undeniable high points. One of those was this album-closing track. It was one of a few songs on the record with which Petty struggled to find the right sound. His solution: Send the tapes off to Robbie Robertson, who gave the song soulful production touches and enlisted his ex-Band-mate Richard Manuel to sing harmonies. It worked beautifully, in large part because Petty’s original song, a tale of a guy alternately wishing the best for a former lover and wallowing in her memory, was so moving to start.

3. “It’ll All Work Out” (from the album Let Me Up (I’ve Had Enough), 1987)

Let Me Up (I’ve Had Enough) is a somewhat forgotten album in the Heartbreakers catalog. Interpersonal relationships within the band were straining at the time (the title probably gives that away), and it’s not surprising that Petty’s next move was his first solo record. Nonetheless, all involved pulled it together on this weeper. As he so often did with Petty’s songs, Mike Campbell added just the right instrumental touch. In this case, a Japanese instrument that’s somewhere between a guitar and a zither. It adds exotic flavor to Petty’s tale of woe. The narrator keeps coming back to the title refrain to convince himself that he can indeed survive without the girl he loves. Or maybe it’s as a way of denying the fact that he was the one to blame for their flameout in the first place.

4. “Echo” (from the album Echo, 1999)

For a long time, Petty didn’t have much kind to say about his 1999 album Echo, complaining that he made it out of obligation rather than inspiration, and that the raw feelings left over from his divorce clouded his judgment about the songs. (He did soften his stance on it before his death.) The title track is emblematic of the oft-harrowing journey he takes on the record. Most Petty songs are known for their concise nature, but “Echo” barrels ahead for five verses over 6 ½ minutes. And still, at the end of it, you get the feeling that he still had more to get off his chest about his conflicted emotions. Instead, he let Mike Campbell do the talking with a furious guitar solo. It’s a fascinating outlier in his catalog, one that leaves every bit of pain and regret on the table.

5. “Damaged by Love” (from the album Highway Companion, 2006)

Petty reunited with producer Jeff Lynne for Highway Companion almost two full decades after Lynne collaborated with him on Full Moon Fever and The Traveling Wilburys albums. They picked up right where they left off, especially on this tender ballad. “Damaged by Love” is a character sketch not unlike “Ruby Tuesday” by The Rolling Stones, in that the girl in question seems to be a free spirit that can’t quite be tied down. At least until the final verse, when futilely reaches out to the narrator for some sort of connection. The timpani in the chorus seem like a nod to their old Wilbury buddy Roy Orbison, who certainly knew his way around the sad ones. So young, and damaged by love, Petty laments, as Lynne chimes in with his high harmonies.

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