Overlandia: The Quest For The Perfect Road Trip Playlist


In Killing Yourself to Live, his 2005 book about a 6,557-mile road trip visiting places where death had played an important role in music — where musicians died or committed suicide, where fatal concert disasters had happened, where Robert Johnson allegedly sold his soul to the devil — Chuck Klosterman discussed the number of CDs he would take with him.

It will take three hours to decide which compact discs to put in the backseat of my Tauntaun. This is the kind of quandary that keeps people like me from sleeping…I have 2,233 CDs. Right now, my eyes are scanning their alphabetized titles and I’m wondering how many will make the cut for my drive across America. This decision will dictate everything. Space will be limited, so I can only select those albums that will be undeniably essential.

I elect to bring 600.

I feel this. The more road trips I take, the more pressure I put on myself: People will be riding in your car for three, four, seven hours. You are responsible for their memories. Which means you are responsible for the soundtrack to their trip. What kind of memories do you want them to have? The music must feel right for the drive. Don’t blow it.

iTunes says I have 75 days of music on my computer right now, 27,346 songs, 130+ GB of everything. Actually, check that — I just deleted the soundtrack from The English Patient, which I believe was my ex-wife’s. Nothing personal; this is a mound of audio to sort through at the beginning of any cross-country or regional journey, on top of packing, ensuring that the car is ready, trying to figure out what to eat, and everything else. You can forget tent stakes, stove fuel, a map to the area, your national parks pass — all those things are replaceable when you arrive wherever it is you’re going. But the music is not. It is important. I mean, come on, do you want to listen to Harvard Business Review podcasts all the way to the desert? (No offense if you do.)

I have meditated at length about the proper amount of music, a la Klosterman, and settled on this equation:

Round-trip Length of Road Trip (in hours and minutes) = Length of Road Trip Playlist x ½

Driving to Moab from Denver? I need a minimum six-hour playlist. We’ll hear some of the same songs on the way back, but twice isn’t too much in one week, or even a three-day weekend. That’s 360 minutes of music, which is roughly 100 songs. Not as daunting. All I have to do is pick my favorite 100 songs of all time, right?

Actually, not so simple. I have made mistakes. There is a certain type of music that fits the road.  Ask anyone what kind of music they listen to, and they’ll doubtlessly say “everything,” or “everything but contemporary country music.” Of course they mean that they’re open to most kinds of music, but they don’t listen to classical that often. Or operas. Everyone listens to “everything.” So what is proper road trip music?

Jazz, to me, is coffee-drinking music, or for the morning, or in airports, trying to remain the calm center of the universe as the world melts down around me in the TSA line or the ticket counter. Hip hop is maybe America’s greatest true organic music, but its rhythm is more suited for walking on sidewalks with headphones on or cruising around cities than it is for long stretches of open road.

Guitars and other stringed instruments are the backbone of road music. Think driving into the sunset, or from the sunrise, endless highway, wheels spinning, 70 mph (or 55 on curvy mountain roads). Contemplative lyrics. Acoustic guitars, slide guitars, banjos. Storytelling. Lyrics about life, traveling, knowing, not knowing, going, leaving. Public Enemy’s “Black Steel in the Hour of Chaos,” while a great song, is not exactly right for this. Bob Dylan’s “Isis” is. Fleet Foxes’ “Montezuma.” My Morning Jacket, “Golden.” Lord Huron, “The Stranger.” Waylon Jennings, Neil Young, Willie Nelson, The National, Springsteen and Springsteen covers, Tallest Man on Earth, people who know how to strum and pluck and tell a good story and/or make you want to stare out the window and scratch your chin.

I have found no true formula, no real list of hard rules. Even when you really get it, it’s only for a few minutes: A feeling when you’re driving somewhere maybe with a good friend, often in the last hours of a day, and the first few seconds of the perfect song come on, and if you turn up the volume loud enough, you are able to create a music video in your mind, and it becomes a memory. If you nail it, every time you hear that song for the rest of your life, you’ll say to yourself, This song always reminds me of that afternoon Nick and I drove into Zion for the first time, or This song takes me back to that week in the desert with my friends. And if you do it right, it doesn’t even matter what the song is about.

Photo of Baja California Sur by Steve Casimiro

Overlandia is the art, science, and romance of driving in the dirt.

{ 3 comments…read them below or write one }

  • Annette

    In February I drove about 8000 miles in 2 weeks through BC and the Yukon and Alaska. That translates to a LOT of time in the car! Imagine my horror when my co-driver (who’s car we were using) announced he wasn’t into music and had only brought a single CD of some bizarre bluegrass. AHHHHH!!! I nearly drove off the first mountain we came to.

  • Matt

    I’m in the middle of crafting a playlist for a drive from New Hampshire to Colorado at the beginning of January, and while going through my music I discovered I have enough Bruce Springsteen to last the whole way…is this a problem? Absolutely not.

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