Canadian Songs For Contemplating
My Mixtape’s A Masterpiece is a weekly feature in which a guest compiles a playlist around some theme. This week, Sarah Bea Milner assembles 12 tracks of contemplative Canadian country music. Read Sarah’s thoughts on each song and listen along to the Spotify playlist on top and/or the YouTube playlist at the bottom of the post.
Summer up here in Canada means one thing: road trips! Whether you’re bumming around the Great Lakes or hanging out near the mountains of British Columbia, there are lots of sights to see here—and even more roads to travel.
Living in the Great White North is a privilege, and we have some of the nicest views on the open road. As an Ontario native, I have a fondness for the local shape of the land: the impossibly tall red pines stretching out straight to the heavens; the rocky Canadian Shield, blast open to allow roads to run through; countless hills and curves through the rural landscape, with trees, lakes and farmland as far as the eye can see. Screw driving on the 401—I’m always going to take the scenic route.
1. “Sudbury Saturday Night” by Stompin’ Tom Connors
The late, great Tom Connors had a knack for getting a crowd going, and that’s exactly the right mood to set when you start a long drive. His hard-driving beats and amusing, folksy lyrics are both effortless sounding and instantly iconic. It’s real “dive-bar” energy, but it’s also unapologetically Canadian and a whole lot of fun.
2. “Back To Me” by Kathleen Edwards
Easily one of the most underrated voices in the Canadian country scene, Kathleen Edwards is at her best with “Back To Me,” a self-empowered, jilted lover song. Everyone has experienced heartache at some time or another, but rather than follow the typical “cryin’ in my whiskey” route, Edwards flips the script. It’s fun, it’s loud, and it’s perfect for the car stereo.
3. “Summerfling” by k.d. lang
The quintessential summer song, “Summerfling” should be on everyone’s playlist. It is peak crossover material—k.d. lang is embracing the adult contemporary genre here, marrying her contralto voice with a more pop-oriented musical arrangement. The song is catchy sure, but it’s also hypnotic—perfect for shifting into the contemplative mindset.
4. “Hasn’t Hit Me Yet” by Blue Rodeo
A Canadian icon for good reason, Blue Rodeo is an alternative country and rock band that eschews country music tropes to produce music that’s unforgettable and endlessly playable. “Hasn’t Hit Me Yet” is a timeless track that feels as relevant now as it did when the single debuted almost 30 years ago.
5. “Truck Got Stuck” by Corb Lund
Corb Lund and his band The Hurtin’ Albertans are on-track to become Canadian country royalty, and it all started with this song. Appearing on his fourth studio album, Hair In My Eyes Like A Highland Steer, “Truck Got Stuck” is the single that made listeners sit up and take note. Lund has a sharp wit and a rapid-fire, unique delivery that makes him one of a kind. It’s a quirky, amusing, and very relatable song about rural life—authentic rural life, not the weird stereotypes that get pushed by today’s Top 40 country.
6. “My Nova Scotia Home” by Hank Snow
Hank Snow is a country legend, but sadly, he’s one of many artists who left Canada to pursue fame and glory in the United States. Snow’s breakout success happened in Nashville in the ‘50s, and he spent the rest of his life as an American. Still, he never forgot his Canadian roots, and in 1968, released the album My Nova Scotia Home. The title track is a sweet ode to the Maritimes, and is the perfect, low-key accompaniment for a summer drive.
7. “Danny’s Song” by Anne Murray
Written by the prolific hit-maker Kenny Loggins, “Danny’s Song” is a ‘70s easy-listening gem. It’s a bittersweet love song with just the right amount of pedal steel, imparting a distinctly country flavor. Murray has a beautiful voice, which she showcases here—without falling into the “diva” trap so many of her contemporaries fell into (I’m looking at you, Reba).
8. “If I’ve Only One Time Askin’” by Daniel Romano
Firmly introspective at this point of the mix tape, Daniel Romano offers an excellent throwback song that marries classic country sound with distinctly contemporary production. Romano loves the old stuff—he rejects the direction country has gone, labelling his retro-inspired sound “mosey”—and that shines through in “If I’ve Only One Time Askin’.” This is alt-country at its finest: smartly written, soulfully sung, and unabashedly earnest.
9. “Spookin’ The Horses” by Fred Eaglesmith
Like Romano, Eaglesmith is another excellent (if underappreciated) alt-country singer-songwriter. While “Spookin’ The Horses” isn’t is most well-known track, it’s easily one of his best songs. The melody is somber, his vocals loaded with feeling. There’s a nostalgic quality here that demands retrospection. It’s a quiet, thoughtful mood-maker.
10. “The Woman In Me (Needs The Man In You)” by Shania Twain
A Canadian country mix tape needs Shania Twain—that’s just the way it is. For a more upbeat trip, you might want “Whose Bed Have Your Boots Been Under” or even “Any Man Of Mine,” but a contemplative road trip? That demands a ballad, and “The Woman In Me” might be one of the best female-sung country ballads of all time. Twain’s performance here is wrought with feeling, and the melody is perfect for her range. Regardless of your age or gender, this is a song that anyone with a heart can relate to.
11. “Sonny’s Dream” by Ron Hynes
Ron Hynes is another underappreciated singer-songwriter. “Sonny’s Dream” is an unforgettable song about loss, adversity, and hope. Newfoundland native Hynes was one of the best lyricists of his generation; the turns of phrase her are evocative and haunting, while the underlying story is heartbreaking. It’s a bleary-eyed anthem, the kind of song that feels universal yet personal.
12. “I’d Go To Jail” by Dean Brody
Sentimental without being cheesy, earnest and surprisingly stripped-down for a recent country song, “I’d Go To Jail” is a song about a father’s devotion to his daughter. It takes the “overprotective dad” rural stereotype and subverts it, going for a gentle arrangement and soft-spoken delivery. Try to find the acoustic version—it’s best heard with just Brody and his guitar.
