4 Tom Petty Slow Ones That Hit Hard After a Breakup

Tom Petty earned renown throughout his career for being one of the most convincing rockers of his or any other generation. But he wouldn’t have been quite as legendary without his mastery of heartbreak ballads.

Time and again, Petty rose to the occasion with songs about lost love. These four tracks will make a direct path to your heart bone if you’re feeling a little lovelorn yourself.

“Insider”

Stevie Nicks kept hounding Petty for a song. Finally relenting, Petty wrote “Insider” for her. And then he decided it was too good to let go. Nicks, a good sport, sang backup on the track, which ended up on Petty’s Hard Promises album in 1981. (And she received “Stop Draggin’ My Heart Around” from Petty as a massive consolation prize.) The title of the album comes from the lyrics to this song: “And I’ve had to live/With some hard promises.” You can hear Petty’s voice practically quivering with emotion when he sings the refrains here, making it feel particularly personal. “Insider” does a devastating job of evoking the feeling one gets when they’re the odd person out of a relationship.

“The Best Of Everything”

The Southern Accents album never quite made it to what Petty originally wanted it to be. He initially thought of it as a concept album about the South, à la what Randy Newman attempted to do with Gold Old Boys. He got sidetracked when he met up with Dave Stewart of Eurythmics and pushed everything in more of a pop direction. But he indirectly landed with a gorgeous closer in “The Best Of Everything”. He had written the song for the Martin Scorsese film The King Of Comedy. Although it didn’t get used for that purpose, Robbie Robertson, who coordinated that soundtrack, ended up adding soulful production touches to the track. Robertson also enlisted former Band members Richard Manuel and Garth Hudson to help Petty on this song about the one who got away.

“It’ll All Work Out”

The 1987 album title Let Me Up (I’ve Had Enough) gives a pretty good indication of where Petty and his Heartbreakers were in their musical journey at the time. Non-stop touring in between albums was getting to them. Having pushed their studio experimentalism to the limit on the Southern Accents album in 1985, they decided to keep things simpler with the follow-up, hustling out the songs quickly. “It’ll All Work Out”, however, feels like one song on the album where they took their time to preserve the delicacy of the emotion. Mike Campbell sets the musical tone by playing the koto instead of a normal guitar. Petty, meanwhile, gets deep inside a character trying to rationalize his way through his regret.

“One More Day, One More Night’

After the fact, Petty felt that his 1999 album Echo, with many songs tied to his crumbling first marriage, might have gone too raw for its own good. We’re of the opinion that the album is just right, following in the imposing tradition of warts-and-all breakup albums such as Bob Dylan’s Blood On The Tracks and Bruce Springsteen’s Tunnel Of Love. The emotional meltdown of it all comes to a head on “One More Day, One More Night”, the thrilling closing track. While Mike Campbell’s guitar clusters circle all around him, Petty pleads for mercy in heart-rending fashion. “No one ever taught me how to be on my own,” he moans. This song gives a harrowing approximation of that lonely feeling.

(Photo by Jeffrey Mayer/WireImage)

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