Ranking the 5 Best Songs on the Late-Period Tom Petty Album ‘Highway Companion’

In 2006, Tom Petty popped up after a four-year recording hiatus with his third solo album. Highway Companion reunited him with producer (and former Traveling Wilbury buddy) Jeff Lynne, who had helmed Petty’s first solo record Full Moon Fever nearly 20 years before.

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Highway Companion features Petty as loose and assured as any time in his career, as he, Lynne, and guitarist/singer Mike Campbell locked into an easygoing recording groove that put the focus on some outstanding songs. Speaking of those songs, here are the five from that wonderful record that we believe are the best.

5. “Ankle Deep”

Petty always rose above the competition in the story-song department because of how he would leave out big chunks of the narrative, but include the key moments that told you all you needed to know. Think of songs like “Something Big” and “Swingin’.” And “Ankle Deep” stands proudly in that line. For as much as we can tell, it’s about a girl who steals a prize horse from her family. But what sticks with you are the killer one-liners that make you chuckle, but also say so much, such as when the girl utters, Daddy, you been a mother to me.

4. “Down South”

Petty envisioned this song as someone returning to his old Southern haunts after a long period away. And, in many ways, it was apropos for him, as he hadn’t written about the region in such expansive fashion since his troubled yet still brilliant 1985 album Southern Accents. On “Down South,” which breezes along with on a wave of good-natured nostalgia, the narrator deals with old mentors, heroes, and ghosts, encounters mistresses and mosquitoes, and does his own Mark Twain impression. Petty ties it all together with a promise to an old lover: I’ll give you all I have and a little more.

3. “Square One”

While Petty is in prime storytelling, character-sketch mode throughout Highway Companion, he occasionally seems to be revealing more of himself along the way. “Square One” finds him singing in exquisitely gentle fashion about leaving the past behind and starting fresh. To do that, the narrator needs to acknowledge misdeeds and wrong turns, almost as if he has to make a penance before he can begin again. In the bridge, he finally gets to a redemptive spot: It took a world of trouble, it took a world of tears / It took a long time to get back here.

2. “Saving Grace”

For the most part, Highway Companion stays on the gentle side musically. Petty explained he wanted to get the feel of a small combo, and he even played the drums himself. On “Saving Grace,” however, this trio rocks with such conviction that you’d swear that all the Heartbreakers showed up to give their input. Framed by a riff that owes more than a little to ZZ Top, “Saving Grace” finds Petty singing in the second person, which gives the lyrics the feel of hard-earned advice. The song suggests you have to keep moving and keep looking for that grace, because the alternative is unthinkable.

1. “Damaged by Love”

For the most part, Jeff Lynne’s production steers on this album steer clear of some of his trademark moves (the super-modulated acoustic guitars and snapping drums, the backing vocals that sound like human wah-wah guitars, and the like). Highway Companion is much more restrained in that respect than Full Moon Fever. But “Damaged by Love” goes into a lusher mode, featuring some Orbison-like traits (the timpani in particular) and Lynne doing Phil Everly-style high harmonies. Petty even gives a shimmering tremolo guitar solo, and it all works wonderfully in service of one of the most heart-rending ballads of his career.

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