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Certain Songs #2476: Steve Earle – “Way Down in The Hole”

November 1, 2022 by Jim Connelly

Album: Washington Square Serenade
Year: 2007

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Right now, Rox and I are in the middle of our third or fourth watch of David Simon’s The Wire, which despite a problematic final season — we are going to once again have a heated discussion about whether what McNulty did was out of character or perfectly logical action by someone driven to extremes by a system that is broken — is still ranked as one of the very best TV shows ever. Right now, we’re in the third season, and very looking forward to the fourth season, which might be the single greatest season of television, full stop.

One of the cool things about The Wire was that every season, they would have a different artist do a rendition of the theme song, Tom Waits’s “Way Down in the Hole,” and Earle’s version was what soundtracked that final season.

Which made sense, because he also acted in it, playing a variation of himself, a recovering addict named Walon. Earle had popped up in the second season (I think), but he has a longer arc in the fifth season.

And while The Wire was the first formal acting job Earle had — though apparently he was an extra in Robert Altman’s Nashville, a film I really need to see again — it wasn’t the last. He turned up again in David Simon’s Treme, again basically playing a variation of himself, as one of massive cast of musicians that made Treme the greatest extended look at a music scene that will ever exist. God, I loved that show, and how it showed the way music can steer us away from tragedy and towards joy, no matter how fucked up life gets.

Anyways, Earle’s take on “Way Down in The Hole” turned up on 2007’s Washington Square Serenade, an album that made a conscious turn away from the electric rock that permeated The Revolution Starts Now and Jerusalem. Produced by one of the Dust Brothers, a lot of Washington Square Serenade was a juxtaposition of electronic drum loops with acoustic instruments, with Earle’s voice firmly on top, like on “Way Down in the Hole.”

When you walk through the garden
You got to watch your back
Well, I beg your pardon
Walk the straight and narrow track

If you walk with Jesus
He’s gonna save your soul
You got to keep a devil
Way down in a hole

And while Earle’s take doesn’t have the rough beauty of the Waits’s 1987 original — I mean, duh! — I kinda love the counterpoint “in the hole / in the hole” looped backing vocals he adds in the later verse, and making the second-best version of a great song is still pretty good, even if probably wrote this post mostly to rave about Treme, which I haven’t really done nearly enough.

Stop reading this, and watch Treme. It’s only 36 episodes. I’ll wait.

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That was awesome, right?

And finally, in 2018, Earle played himself in an episode of the TV show Nashville, and I wonder if that makes him the only person to appear in both the film and TV show, which, I should point out, have nothing to do with each other outside of the name. Anyways, I wouldn’t even begin to know how to research that.

“Way Down in the Hole”

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Filed Under: Certain Songs Tagged With: Steve Earle, Washington Square Serenade, Way Down in the Hole

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Previously on Medialoper

  • Certain Songs #2580: Supertramp – “Even in the Quietest Moments”
  • Certain Songs #2579: Supertramp – “Bloody Well Right”
  • Certain Songs #2578: Supergrass – “Sun Hits The Sky”
  • Certain Songs #2577: Supergrass – “Alright”
  • Certain Songs #2576: Superchunk – “If You’re Not Dark”

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