The Road Trip Playlist To Blast Before You Read 'Jess, Chunk, And The Road Trip To Infinity'

The road trip playlist can make or break a journey. In fact, creating one is an extremely important task, right up there with checking the oil and getting gas before heading out. It’s what responsible long-distance travelers do.

There has to be a balance of tunes, and it can get pretty nuanced. If you play the wrong song at the wrong time, you can kill the moment. We like up-tempo songs, ones we can rock out to in the beginning of the trip, but we also need downbeat songs that allow us to reflect, staring broodily out the window when the road conversation turns quiet. We need songs that can be played passive aggressively when we don’t get our way about stopping at Arby’s, and we need songs that pull us back together again, reminding us of how much we adore our fellow passengers.

Jess, Chunk, and the Road Trip to Infinity is a novel about a transgender girl and her best friend who take to the open highway just after high school graduation. Their destination is Chicago, and Jess’s estranged father’s wedding. After all, nothing says “Screw you, Dad” like showing up to his wedding in a dress when he used to make you wear a Boy Scout uniform.

Below is the playlist I put together for Jess, Chunk, and the Road Trip to Infinity. I think it covers key moments in their journey, as well as my own:

1. "The Distance" by Cake

I love starting out a trip with this one. It has the drive and excitement of pulling out of the driveway and going off on an adventure. It kind of cracks me up that Jess and Chuck are doing this in a Honda Insight – not exactly a racecar:

“He's going the distance/He's going for speed

She's all alone/ In her time of need”

2. "The Yip Song" by Robyn Hitchcock

This continues the energy of the first song, and even amps it up a little. Who doesn’t love sing-shouting, “Yip, Yip, Yip, Yip, Yip!”

“Vera Lynn, Vera Lynn/Love will come of all our sins/

Painted on my tail fin now Vera Lynn”

3. "I'm Gonna Be (500 Miles) by The Proclaimers

An incredible feel-good song. I’m pretty sure Jess and Chuck have the whole Scottish accent thing down too.

“But I would walk 500 miles/And I would walk 500 more

Just to be the man who walked 1,000 miles/To fall down at your door”

4. "Everyday Is A Winding Road" by Sheryl Crow

This song is perfect for finding the rhythm of the road – sort of like you do when you’ve left behind the city or town you came from.

“Every day is a winding road/I get a little bit closer

Every day is a faded sign/I get a little bit closer to feeling fine”

5. "Fast Car" by Tracy Chapman (Studio Version)

I like the melancholy words and hopeful melody here. It’s a good song to listen to while contemplating a relationship – maybe one you have with the other person in the car.

“You got a fast car/I want a ticket to anywhere

Maybe we make a deal/Maybe together we can get somewhere”

6. "Emperor of the Highway" by Todd Rundren

Every road trip soundtrack needs one surprisingly funny song. Played at the right time, it can dispel any potentially creeping tension. In the book there’s a moment when Jess offers to drive, and Chuck seems unwilling to give up the wheel – Jess thinks he’s a little controlling. If this song were to come on just then, I think they’d both laugh.

“I am the Emperor of the Highway

I wield the Universal Will”

7. "To Those Who Fight Further" by The Black Mages

I only know about this instrumental song because I listened to it with my daughter on a road trip we took. In fact we listened to several songs by Nobuo Uematsu, an amazing video game soundtrack composer. The song itself has drive – and may even be helpful in urging a first generation hybrid Honda Insight (without much natural oomph) up a hill.

8. "Graceland" by Paul Simon

This song is another great find-the-rhythm-of-the-road song. Perfect for when the terrain flattens out after a chug up a steep grade; kind of like getting to highway 80 after the laborious climb up 680 out of the East Bay of the San Francisco Bay Area.

“The Mississippi Delta was shining/Like a National guitar

I am following the river/Down the highway/I'm going to Graceland”

9. "Interstate 8" by Modest Mouse

Ya gotta love a road trip song that’s really a song about staying in the same place.

“I'm on a road shaped like a figure 8

I'm going nowhere, but I'm guaranteed to be late”

10. "Geek in the Pink" by Jason Mraz

A must-include song on every road trip playlist is at least one that has fast, intricate, and difficult lyrics. A song you can sing at the top of your lungs with your best friend, for the sheer joy of it. One that leaves you both with a profound sense of accomplishment only rivaled by say… getting a perfect score on your SATs.

“Well let the geek in the pink take a stab at it/If you like the way I'm thinkin' baby wink at it/I may be skinny at times but I'm fat full 'a rhymes/Pass me the mic”

11. "Raise Your Glass" by Pink

An incredible feel-good anthem, tailor-made for protagonist Jess who’s fine with being trans but wonders if the rest of the world will come to terms with who she is.

“So raise your glass if you are wrong,/In all the right ways,

All my underdogs,/We will never be never be, anything but loud”

12. "Birdhouse In Your Soul" by They Might Be Giants...

An excellent follow-up to the preceding song, and a love-letter to friendship. One of my best friends is another author named Jim Averbeck. This song found its way onto the Jess and Chunk playlist because we take road trips together on our way to conferences and writing retreats. No journey is complete without this one, and I don’t think a road trip would count if it weren’t played. In fact, I’m pretty sure that not playing it would likely create some sort of a cosmic tear that would endanger the universe.

“Not to put too fine a point on it/Say I'm the only bee in your bonnet

Make a little birdhouse in your soul”

13. "This Must Be The Place" by Talking Heads

Let’s face it, a little rain must fall during every road trip. Your friend gets on your nerves a bit, or says something that hurts your feelings. This is the perfect passive-aggressive song to play at this point, because it’s a ballad to home but by the end it’s filled with so much love you can transfer to the person you’re with. Poof. No need to own or admit your feelings.

“Home is where I want to be/Pick me up and turn me around

I feel numb, burn with a weak heart/Guess I must be having fun”

14. "Kiss Off" by Violent Femmes

Then again – sometimes your friend isn’t ready to kiss and make up. I like the energy of this song, and I picture Jess singing it at the top of her lungs, howling, then shrieking her guts out before going full-bore into raw-throat mode after Chuck decides he’s not going to Jess’s dad’s wedding because he’s going to stay behind in Iowa with a girl he just met.

“You can all just kiss off into the air/Behind my back I can see them stare

They'll hurt me bad but I won't mind/They'll hurt me bad they do it all the time”

15. "How Did I Get Here" by Odesza

Perfection for that what-just-happened, why-did-my-best –friend-abandon-me -and-could-my-own-behavior-have-caused-this, contemplative moment.

“How did I get here?/How did I get here?

How did I get here?/How did I get here?/How it is true”

16. "Heroes" by David Bowie

You know that feeling when you’re hurting and sometimes there’s something exquisite in that hurt… something almost savory as you review images in your mind of your time with another person? This song perfectly evokes that sensation.

“Though nothing, will keep us together/We could steal time,

just for one day/We can be Heroes, for ever and ever/What d'you say?”

17. "Sweet Jane" by Cowboy Junkies

More melancholy – a perfect sunset of a song. It’s the end of the day, the nervous excitement of the trip has faded, and you need a slow-ish, beautiful , mellow song.

“Anyone who's ever had a heart/wouldn't turn around and break it

And anyone who's ever played a part/Wouldn't turn around and hate it”

18. "Chicago" by Sufjan Stevens

Love, love, love this song and not just because it’s called Chicago, which is the final destination for Jess and Chuck’s road trip. It’s the perfect soundtrack ending for an indie film; acknowledging love and mistakes in a way that haunts at the end of the day.

“I fell in love again/All things go, all things go

Drove to Chicago/All things know, all things know

We sold our clothes to the state/I don't mind, I don't mind

I made a lot of mistakes/In my mind, in my mind”

No matter where you end up or who you end up with, remember it’s the journey, not the destination.

Images: Travis Hezel/Unsplash