Top 5 Deep Cuts from Tom Petty and the Heartbreakers

Tom Petty and the Heartbreakers released 13 albums over four decades, starting with their 1976 self-titled début. Petty, rightfully, holds rank in the American songbook beside Bob Dylan and Bruce Springsteen. He was backed by one of the best bands in the business and together they recorded albums that are deep with rich songs and inspiring performances. It’s worth highlighting the overlooked cousins of the Heartbreakers’ better known cuts. 

We miss Tom Petty, but thankfully we can hear his voice any time we choose to gently put the record needle down, patiently wait for the warm crackle of vinyl, and enjoy the work left behind by one of the great American songwriters. 

Below are five deep cuts from Tom Petty and the Heartbreakers. 

1. “Shadow of a Doubt (A Complex Kid)” from Damn the Torpedoes

I think she loves me but she don’t wanna let on
Yeah, she likes to keep me guessing
She’s got me on the fence with that little bit of mystery
She’s a complex kid and she’s always been so hard to figure out

Tom Petty and the Heartbreakers’ album Damn the Torpedoes was released in 1979. The album opens with “Refugee,” followed by “Here Comes My Girl.” “Don’t Do Me Like That” is track 6, but there’s a gem on the album many might have missed.

“Shadow of a Doubt (A Complex Kid)” is a classic piece of narrative rock and roll from Petty and company. Petty’s muse in “Shadow” is stubbornly mysterious, she dreams in French but doesn’t remember anything the next morning. She keeps him guessing and leaves him “with a shadow of a doubt.” Petty is frustrated by the game she’s playing, but is equally attracted to her mysterious ways. It’s the Seventies and young love has patience for a flirty kind of hide and seek. 

2. “Something Big” from Hard Promises

On “Something Big,” Tom Petty echoes the sound of Neil Young. The character-driven lyric is supported by a Drop-D tuning, a la Crazy Horse. 

Speedball rang the night clerk
Said, “Send me up a drink”
Now the night clerk said,
“It’s Sunday man, wait a minute, let me think.
There’s a little place outside of town. Might still have some wine.”
Speedball said, “Forget it, man. Can I have an outside line?”

“Something Big” is the story of a man named Speedball and his fateful night in a hotel room with a sex worker. Speedball isn’t looking for romance, but he needs someone he can trust. The story ends when the hotel maids find him alone and dead in his room. Petty—emphasizing and sneering like Dylan—sings, “It’s probably just another clown working on something big.”

3. “Louisiana Rain” from Damn the Torpedoes

Two songs on Damn the Torpedoes date back to Petty’s pre-Heartbreakers band, Mudcrutch (that band also featured future Heartbreakers Mike Campbell and Benmont Tench). “Don’t Do Me Like That” was an early Mudcrutch song as was the album closer, “Louisiana Rain.” 

Louisiana rain is falling just like tears
Running down my face, washing out the years
Louisiana rain is soaking through my shoes
I may never be the same when I reach Baton Rouge

“Louisiana Rain” is a lonely road ballad of a weary traveler who’s changed by the places he visits. There are two ways to interpret this song. One way is a hopeful rebirth with the rain “washing out the years.” This could be read as a cleansing of past mistakes. There’s also sadness to this resignation that he won’t be the same man by the time he reaches home in Baton Rouge. The experience of being born again doesn’t seem like a choice. It was brought on by hard life, and here the resignation is submission.

4. “Straight into Darkness” from Long After Dark

Long After Dark is a closing chapter for Tom Petty and the Heartbreakers. Howie Epstein replaced Ron Blair on bass after the band had been on tour, seemingly nonstop, for years. Tom and band sound burned out on this record. “Straight into Darkness” is about a girl, but it could be a metaphor for where the Heartbreakers were at the time. 

There was a moment when I really loved her
Then one day the feeling just died
We went straight into darkness
Out over the line
Yeah, straight into darkness
Straight into night

But a new chapter was beginning for the band, too—Southern Accents would be the next album. There’s a flicker of hope in “Straight into Darkness” in the following verse:

I don’t believe the good times are over
I don’t believe the thrill is all gone
Real love is a man’s salvation
The weak ones fall, the strong carry on

5. “Swingin’” from Echo

Tom Petty wrote “Swingin’” while the band was in the next room trying to improve on a track they had already recorded. Petty walked into the room and told the band he’d written something better than what they were working on. 

And she said I’m never going back
She said at last I’m free
I wish ma could see me now
She’d be so proud of me

Echo was the last album to feature bassist Howie Epstein, who died of a heroin overdose in 2003. Epstein famously missed the photo shoot for Echo. “Swingin’” was released as the third single from the album, but never reached the same popularity as the band’s better-known songs.

She went down swingin’ like Glenn Miller
Yeah, she went down swingin’ like Tommy Dorsey
Yeah, she went down swingin’ like Sammy Davis
She went down swingin’ like Sonny Liston

Photo by Michael Ochs Archives/Getty Images