11. Brandi Carlile (with Kris Kristofferson)
This has “I am going to make the best of it but it is going to be very, very hard” written all over it. You have been looking forward to this holiday for months, curating a playlist that hits all the right songs at certain bends in the road or stretches of highway that need an emotional boost.
But you did not anticipate him joining you. You hope he decides to just sit back and read the whole time so the two of you can catch up, enjoy your handiwork, but he won’t stop trying to engage both of you, and it’s clear that he can mostly assert his academic dominance. He has some opinions about Lorrie Moore, about Leon Trotsky, and you’re not sure where he made the jump from one to the other because it is all just so teeth-grindingly dull. Your friend attempts to chime in, and you wait on edge to hear a silvery rebuttal, but he keeps talking over, his smoker’s growl somehow filling this entire stretch of Highway 60. You fantasize about him being eaten by a moose.
10. Michelle Branch
You’re not sure how you ended up agreeing to drive a bubbly American undergrad from Vancouver to Calgary, and you can’t help but think this is how most fanfics start. We’ll probably have to share a tiny bed in a motel during a rainstorm after the car breaks down, you think. She brings you a box of Timbits when you pick her up, a sweet gesture, although you can’t help but feel the bubbling of annoyance when she spends three minutes Instagramming the box.
You worry about filling the space with conversation with a stranger, but she’s more than got you covered. She knows an awful lot about the Jamie Salé/David Pelletier skating controversy, enough for the entire length from Kamloops to Salmon Arm. She finds Justin Trudeau attractive, and tells you such, and spends the stretch from Banff to Calgary gushing about the pictures of him marching in Pride parades. It must be so nice here, everyone seems so welcoming. “Lovely,” you say through a slight grit, and try to focus on the outskirts of the natural wonder around you.
9. Aaron Tveit
He says he feels at home in the mountains and woods because he attended and worked at a summer camp long after all his friends started to get internships and summer jobs closer to home. He was a songleader, warbling “Land of the Silver Birch” and “Stand By Me” with the fullness of his chest for half-interested tweens.
When you pull into the grounds of Banff, he practically squeals, jumping at the chance to help you repack more efficiently as you prepare for a hike. He pleads with you that he knows what he’s doing and remembers a particularly beautiful path from a wilderness trip he took some teens on years ago. He sings three verses of “American Pie” at full gusto (“to let the mountain lions know we’re here”) before you indulge him on and we were all in one place.
He gets you lost and forgets the sunblock. You’re both miserable, burnt and exhausted that night. He spends the rest of the trip desperately trying to make it up to you by offering to help, but accepting it becomes more exhausting than him asking.
8. James Blake
He brings along sandwiches from the fancy deli near his apartment for the first leg of the trip and remembers your order, right down to the substitution of your favorite cheese. He pauses as if he’s waiting for a thank you.
He writes a lot of short stories where the protagonists are always women, usually cis white women in their twenties in some blank Midwestern city, and they are always in love with The Worst Kind of Men, and they spend a lot of time taking baths or alone at their kitchen tables, drinking coffee. He tells you about the literary magazine he was accepted to, shrugging like it’s no big deal. He says anyone can be a writer. When you tell him you have difficulty calling yourself “a writer,” his jaw tightens. He becomes indignant, like how dare you not share the fullness of your talent with the world?
He takes too many bites of an edible before you head to Yoho and is too afraid to get out of the car and look down at the expanding green of the forest. His eyes are now a pair of wet reflective moons and he asks you to hold his hand.
7. Diana Krall
Maybe it’s your desire to turn every long drive into therapy but you find yourself curling with frustration because it feels like she’s holding back, that she’s saying things that are lovely and profound about the scenery and the state of things but it still feels like the surface of a half-frozen lake.
She has a lot of opinions about kitchen backsplashes. It’s okay. So do you.
6. Sara Bareilles
Making a stop at Niagara is her idea, and she’s so excited she gets up early and picks up coffee for the both of you. She doesn’t talk much on the drive east, lets you go on about your job and your hookups and whatever else pours out while on the road. She is polite and dutiful with offering to pay for gas, to drive when your eyes start to get heavy. She lets you control the music and tolerates your need to restlessly station-surf, insisting on leaving a song on only once, and you’re surprised by how much life and gusto she gives to “Any Man of Mine.”
She insists that she’s straight but in the spartan room you share after visiting the falls, she eschews the second bed and curls into you as possible, your thinning grey t-shirt barely a buffer from the warmth of her arm wrapped around you. Right before you drift off, you swear you feel her press a kiss to the place where your neck and shoulders converge. She sings “River” in the shower in the morning.
She buys the tourist photo of the two of you on the Hornblower boat, soaking and smiling, and can’t wait to show it to you. You roll your eyes and pretend you’re above it, but you buy one, too.
5. Javier Colón
Same earnest summer camp songleader energy as No. 9, but his company is a little less grating. He is unafraid to ask questions or consult GPS when he doesn’t know how to get back to the main highway.
4. Prince (studio)
Communicates almost entirely in changes in eye contact and gestures. Insists on going to the Grand Gathering in Sainte-Flavie as you make your way down the St. Lawrence River and spends half a day just watching the way the sun dances on the humanoid sculptures in the water, occasionally taking out a notebook to pen some observations and sketches as they slowly fade into the tide. When you ask why, you are met with the reply, “I came to see some familiar faces.”
Neither of you have ever been to Sainte-Flavie.
3. k.d. lang
You’re not sure how she managed to pack every possible road trip essential, from gauze to granola, in such a small, spare backpack. When the car gets a flat around Moncton, she insists you repair it because you’re going to need to know eventually but is gentle and patient as you stare at the job, terrified you’ll break something of hers, or the car, or ruin this after it’s all gone so well.
She can sense the change in your disposition and breathing as you approach the Confederation Bridge and asks what’s wrong. You admit that you’re afraid of driving over long bridges and she says nothing, just dutifully gestures for you to pull over and she takes over driving, leading you both over the icy sea, never dropping focus as you white-knuckle her hand. When you reach the Northumberland Strait, you can see the gentle light in her eyes grow brighter.
There’s a warm, appreciative reverence to everything she says or does about this place, one you’ve only seen as a descriptor for bivalves on pretentious gastropub menus or reading Anne of the Island as a child. It’s not a dramatic, thrashing praise but the hushed joy of walking into an old, gorgeous cathedral or coming home after a 12-hour day, relieved to crawl into bed and shift the weight off your body.
Later that night, you can just tell she’s wide awake although you’ve both been lying in bed for hours. “What’s wrong?” you ask.
“I’m terrified of climate change,” she admits.
“Me too,” you offer, and spend the rest of the night half-awake, clinging to her like a koala.
2. Prince (live)
There’s a moment in Prince’s 1983 live version of “A Case of You” while, treading through a bioluminescent sonic pool of his own making, Prince gets up off one knee and squeezes his eyes shut, and it looks as though he’s about to say something or stifle a lump in his throat, like he’s fully internalized the next verse of “A Case of You” and it’s breaking his heart in slow motion.
The other ones were imagined but this one is real, and not in Canada. A few years ago, I accompanied a dear friend on a visit to a wolf sanctuary in southwest Indiana. We left Chicago during rush hour, hours lurching in traffic before congestion gave way to road-movie idyll. It’s likely we even listened to “A Case of You” on that ride at some point before arriving, exhausted, at a Best Western just over the state line in Ohio. As we faded off under the blue light of a Friends re-run, we said to each other, “I’m glad you’re here,” and it felt heavy with exhaustion and significance.
The next day, as we pulled out of the sanctuary, I felt that same lump, trying to carefully monologue around it about the importance of welcoming joyful experiences into your life, trying to release just enough of the valve to ease the pressure without unnecessarily flooding us both. (I still overdid it. I always do.)
Maybe it’s because it always takes us as queer people a little longer to grow into our full selves and cultivate genuine relationships as our full selves but sometimes I feel like the world makes dragons of us, desiring to sleep on piles of memories and life-affirming experience, digging at intimacies with claws spread. Everything has to Mean Something. Everything has to be the light reflecting off the water or the dancing falsetto on surely you touched mine.
That first journey you take with Your Person, your camerado, even if it’s just across the street, feels electric and new and how have I never heard this before? The way Prince croons the love is touching souls bit while the Revolution rain atmosphere on everyone screams an intimate moment that you want to cling to forever, and you want it so badly to mean as much to the person next to you as much as it does to you. It’s expansive, and urgent, and still loudly grateful, just like any good road trip memory.
1. Brandi Carlile (solo)
I’m not sure which came first, my love of “A Case of You” or my love for Practical Magic, where Nicole Kidman’s Gilly Owens poisons her shitty boyfriend and then drives across the country, singing “A Case of You” as the sun sets in the lonesome Southwest, and she appears to sing it the whole way back to her childhood home and the bedside of her grieving sister, played by Sandra Bullock. I love Practical Magic like I love anything that was underappreciated in its time and features Stockard Channing. I love it because it’s a story about working through generational trauma and loving each other, or at least tolerating each other long enough to excise shitty boyfriend demons from your neighbor’s house.
Practical Magic is also a story about longing, and about loneliness, a movie with “being the only one awake in the house at 2 a.m. and thinking about driving across the country to tell them i love you i need you i am sorry for what i didn’t say before” energy. Brandi Carlile performs “A Case of You” with that energy, too—southwestern-highway expansive, insistent enough that you cannot listen to it without picturing who you would draw on the back of a cartoon coaster in the blue TV-screen light, who you would monologue everything to, who makes you sway. Her version of “A Case of You” is in a place beyond road trip companion, but stands at your back whispering go, insists your heart and theirs are worth telling the truth.