While the invention of iPods made things far easier than the days when we had to go through stack and stacks of cassettes to create the perfect on-the-road mixed tapes, there’s still an art to creating the perfect road trip playlist. It takes time, thought, a sense of humor, and a wide-ranging music collection in whatever digital format you prefer. It also needs a theme. It can be about a mood, a time of day, your love for hot dogs, or whatever. You don’t even have to announce the theme. You don’t have to name the playlist “hot dog music” but, to make it all hang together, the theme must, at least, be in your mind during the song selection process.
When Sophia suggested we each create a playlist perfect for a road trip within the 50–but just a 10-song playlist–I was all ooh, fun! until the pressure smacked me. You all turned into the the picky picky music snob staff from High Fidelity. But I forged ahead, tossing beloved tunes out of the way in order to create what could be the best mix of all time (especially when combined with Sophia’s dazzling list of goodness). OK, it’s not the best of all time. But I dig it. Mildly nervous and semi-sensitive being that I am, my temptation is to make apologies for my list or cheat and try to add things in but…I won’t. Instead, I say….have at it. Comment away.
But, when you drive out into America, tunes a-blazing, please remember: enjoy and behave. After all, you don’t want to end up singing the Folsom Prison Blues.
America (Simon & Garfunkel)
There are a few reasons it’s on the list: 1) It’s an umbrella policy that eases some of the guilt of cutting so many state-named songs off my final choices. 2) It’s a damned good song. I have yet to find somebody who dislikes it. If that person exists, I have a feeling I wouldn’t want to know him. I definitely wouldn’t want to travel with him. Would you?
Oh, Atlanta (Alison Krauss & Union Station)
There’s a line in it that sums up how I feel about so many of the places I’ve visited around America: “I hear you calling. I’m coming back to you one fine day.”
Stars Fell on Alabama (Billie Holiday. Wait, Frank Sinatra. No, it’s Billie’s version.)
It’s the story of a perfect moment of beauty and joy in somebody’s life. It’s, I think, part of what we’re all looking for when we go out on the road. Oh and Billie’s voice? Yeah, talk about heavenly.
My Clinch Mountain Home (The Carter Family)
It’s always good to remember where you came from–no matter where you’re going.
Rapid City, South Dakota (Kinky Friedman & The Texas Jewboys)
Some people may dismiss Kinky Friedman as a bit of a novelty act. He’s not. While there are definitely some good knee-slappers (and plenty of reasons to take offense) in some of his songs, this one is just the story of a boy heading out on the road.
Bus to Baton Rouge (Lucinda Williams)
If I had to choose just one album to take on the road, it would be Lucinda Williams Car Wheels on a Gravel Road. But, if we’re talking place names, Bus to Baton Rouge from the album Essence is the way to go. It isn’t the cheeriest of songs–it’s about going back to a home that was, more often than not, a sad place to be. But it’s beautiful.
Nashville Jumps (Cecil Grant)
A great reminder that places are much more than their stereotype. Nashville may be the epicenter of country music, but that’s not all there is to it–and its past was far more varied as well.
Alaskan Nights (David Schwartz)
Never heard of it? Well, it’s obscure in an odd way. It’s from the Northern Exposure soundtrack. The show kicked off my mad love for Alaska. The piece still makes me smile. (Seriously, the whole soundtrack is good fun. Give it a shot. It’s also a great housecleaning soundtrack.)
Thick in the South (Wynton Marsalis)
This piece is one long hot sultry night (or, in this case, drive). It’s Louisiana or Alabama or wherever in August, and the car air conditioner is just barely holding on.
Jack & Neal/California Here I Come (Tom Waits)
Tom Waits is a night in a town you’ve never been to–slightly welcoming, slightly off-putting. He’s essential.
Ooh, got a little sad there at the end. This should lighten things up. Ladies and gentlemen, Simon & Garfunkel…
[youtube=http://www.youtube.com/watch?v=Od66bhNzBtE&hl=en&fs=1]

Makes me realize that my road trip lists are much more obscure… y’all skewed so country!
I add:
This Road I’m Traveling or In Love With a View–Mojave 3
A Sorta Fairytale–Tori Amos
Freeway–Aimee Mann
I Wish I Was the Moon–Neko Case
When It Don’t Come Easy–Patty Griffin
Anything by Expose
xo-M
I SOOOO would have voted for Kinky Friedman a few years ago if I lived in Texas.
Hey Mikel — Yep, we all have those obscure lists, but one of our personal criteria for these lists was that the songs had to have a state name in them …
Kinky may run again but take the whole thing more seriously this time. I didn’t vote for him because he wasn’t presenting a platform, he was just being Kinky. Which is fun but it didn’t give me much confidence.
“Why the hell not?” will forever be my favorite political slogan.
Oh Mikel — Believe you me, there’s some wacky obscure stuff on my other playlists. But, as Sophie mentioned, we put some restrictive parameters on these lists. As it turns out, it seems that country artists anchor their songs in American place names with far more frequency than other genre artists.
And Chris — I think I’m going to borrow “why the hell not?” as my new personal life mantra. Well, not new — I don’t really have one — so I guess it’ll be my first and only.
[...] site. Turns out a whole lot of people like to search for road trip playlists. The lists Sophia and I posted long long ago still pull in the eyeballs. (Yes, that makes us feel [...]