Tom Petty's 10 greatest deep cuts

Tom Petty in September 2017

Tom Petty in September 2017 Amy Harris/Invision/AP

It was summer 2014 and I’d just discovered how drivable Winnipeg was from the Twin Cities.

Checking the concert listings for The Peg I saw Tom Petty and the Heartbreakers, who I had been a fan of since high school but had never seen live. The rock legend and his group were skipping Minnesota on the tour behind that year’s Hypnotic Eye, so there was no talking me out of this one.

My dad, a Petty virgin himself, flew up from Colorado to be my highway companion. It was a beautiful August day well past Fargo, but by the time we got to the outskirts of Winnipeg, the Manitoba rain was falling like tears.

When I reached a biblically flooded interstate underpass near downtown, I was faced a with a choice -- pull over on the side of the road like so many other stranded motorists and tell myself I’d see Petty some other time, or put my car into reverse and back up a whole city block (while switching lanes as other cars cautiously approached) to find a route where my Camry wouldn’t become a submarine. We made it to the concert, and we had a great time.

To keep us rocking all the way to Canada, I had carefully sequenced a massive 40-song playlist for when we’d exhausted the essentials -- Damn the Torpedoes, Hard Promises, Full Moon Fever, and the like. What follows are my lesser-known favorites from that list, the absolute wildest of Petty’s many flowers. You probably won’t hear these on the radio alongside “Free Fallin’” or “I Won’t Back Down” in the weeks to come, but these are my top 10 Tom Petty deep cuts.

Rest in peace, Tom.

10. “Room at the Top” (Echo, 1999)
Echo was the final album to feature longtime Heartbreakers bassist Howie Epstein before he died of a heroin overdose in 2003. Knowledge of his fate casts a pall over the 15-track LP and lends an eerie calm to its opener, especially when you consider that Petty also suffered through heroin addiction throughout the ‘90s. “I got a room at the top of the world tonight,” Petty claims as Mike Campbell’s shimmering guitars lead the listener to the cloud Petty’s sitting on. “And I ain’t coming down.”

9. “Built to Last” (Into the Great Wide Open, 1991)
Into the Great Wide Open sports my absolute favorite album cover of all-time, which might color my appreciation for the first all-out pop album Petty made with the Heartbreakers. Alternating between rockers and ballads, the record’s admittedly spotty back half does feature a gem in its finale. Petty sings lines “I want her more than diamonds/I want her more than gold” and “Come to me, my darlin’/Hold me while I sleep” with a relaxed cool. Built to last, just like the Tom Petty songbook.

8. “Dogs on the Run” (Southern Accents, 1985)
Southern Accents is best known for its decidedly not-southern first single, the psychedelic, sitar-led “Don’t Come Around Here No More,” and its Alice in Wonderland-inspired music video. On the rest of the album, though, Petty is at his heartland rock best, singing about his Florida roots through tales of characters like troublemaker Spike and new car owner Mary. The Heartbreakers really gel on the penultimate track, a Springsteenian ode to youthful restlessness. “Honey,” a “young bleached blonde” tells the beach-stranded narrator, “I discovered early in life there’s ways of getting anything I want.”

7. “Insider” (Hard Promises, 1981)
“Stop Draggin’ My Heart Around” is the duet that Petty and Stevie Nicks will be remembered for, but “Insider” is a real treat as well. “Draggin’” was originally slated to appear on Hard Promises before Nicks used it on her debut solo album instead. Its understudy isn’t nearly as urgent or immediately catchy, but Nicks’ vocals are angelic and Petty has rarely sounded as emotionally vulnerable as he does singing “I bet you’re his masterpiece/ I’ll bet you’re his self-control.”

6. “Kings Highway” (Into the Great Wide Open, 1991)
Playing in the Traveling Wilburys earned Petty a degree from the George Harrison school of songwriting. “King’s Highway” is every bit the pop song as its predecessor on the album, “Learning to Fly,” and that’s saying a lot. When I lived in Uptown, this song would naturally pop in my head every time I walked past Kings Highway, which borders Lakewood Cemetery to the east.

5. “Crawling Back to You” (Wildflowers, 1994)
Petty’s music couldn’t often be described as “majestic,” but there’s no better descriptor for this downtrodden ballad (which might give some insight into Petty’s drug problem). “The ranger came with burning eyes/ The chambermaid awoke surprised/ Thought she’d seen the last of him/ She shook her head and let him in,” Petty sings as Benmont Tench’s plaintive piano winds its way through that beautiful vocal melody. I was elated when he busted this one out in St. Paul four months ago today.

4. “Straight into Darkness” (Long After Dark, 1982)
Despite including the hit “You Got Lucky,” Long After Dark still hasn’t gone platinum 35 years later. Without the musical diversity of Hard Promises or the birthplace anthems of Southern Accents, the back-to-basics album that came between them is often forgotten. But the melodic marriage of Tench and Campbell is a force to be reckoned with on this rocker of the “Refugee” vein. “I remember flying out to London/ I remember the feeling at the time,” Petty yearns before leading the band into a thunderous chorus. “We went straight into darkness/ Out over the line.”

3. “The Dark of the Sun” (Into the Great Wide Open, 1991)
Bonnie Tyler this, Bonnie Tyler that – where was “The Dark of the Sun” during all the eclipse hoopla this summer? It’s a far better tune and more apropos of how that moment unified us in these divided times: “In the dark of the sun/ We will stand together, yeah we will stand as one.” The fifth track on Wide Open also features Petty’s most epic lyrical imagery, with lines like “I saw you sail across the river underneath Orion’s sword” suggesting the singer may have listened to The Joshua Tree a time or two.

2. “Shadow of a Doubt (A Complex Kid)” (Damn the Torpedoes, 1979)
Petty was often at his best when painting musical pictures of women: “American Girl,” “Here Comes My Girl,” “Free Fallin,.” “Complex Kid” is one of the finest examples of his signature style, without a shadow of a doubt. On this energetic standout from one of Petty’s most beloved albums, we learn just enough to let our imaginations run wild -- she hates her boss, when she dreams she seems depressed (until this year, I thought the line was “sometimes she sings in French”) -- while the singer keeps on the edge of mystery.

1. “Louisiana Rain” (Damn the Torpedoes, 1979)
This musical travelogue is perfect. The lyrics take the listener all the way from San Diego to South Carolina and down to Baton Rouge, while the Hammond organ intro and slide guitar solo send us to parts unknown. As much as on his biggest hits, it’s on less frequently celebrated album tracks like this that Petty showed himself to be one of our greatest songwriters.