Tolstoy once wrote, “Music is the shorthand for emotion.” Valentine’s Day is a wonderful excuse to get emotional, let loose the helpless romantic inside and binge your favorite love songs. Or heartbreak songs, as the case may be.
Two quick disclaimers: I’m a touring folk singer-songwriter, so this list will skew heavily toward folk, singer-songwriter as well as the music that moved me at live performances.
I’m also only considering originals. For some of the smoothest, most romantic covers around, I’d point you in the direction of Eugene jazz singer and local legend Halie Loren’s 2024 album Dreams Lost and Found, or any live performance by the classically trained soprano Siri Vik, who often performs early 20th-century American classics at The Shedd Institute.
Let’s dive in!
“I Just Wanna Dance With You,” R.O. Shapiro
Recommended for: letting work wait and dancing in the living room. This track — produced by Phil Cook and featuring Riley Calcagno on fiddle — includes some of R.O. Shapiro’s best writing and singing yet, I think. He counts Sitka, Alaska, as one of his many homes, and performed this tune at Tsunami Books last year opening for May Erlewine.
“Optimist,” Ollella
A moody meeting of minds happens in this brand new Ollella tune: optimism versus pragmatism. Ollella encourages empathy between the two, which I see as an act of love. Ollella is an amazing Seattle-based cellist who often loops her voice and cello live, but this track eschews her sometimes classical tendencies for a mellow indie rock sound.
“Tangled Up In You,” Jacob Miller
Boy, am I a sucker for a good horn section, and this upbeat tune has a killer trumpet chart. Jacob Miller is a Portland singer-songwriter and a friend of mine whom I’ve opened for a few times, and I can confirm his voice is just as angelic live as on this recording. Don’t miss his earlier single “Cherry Blossoms,” a smooth morning meditation.
“Disposable Camera,” Anna Tivel
A love letter to a soon-to-be born child, a future generation, to the vibrant world around us. That’s what I hear in Anna Tivel’s single off her 2024 album Living Thing. Besides the delightfully delicate instrumentation, I love the sense of wonder in her lyrics, and her light vocal delivery. This Portland-based songwriter writes music that is philosophical and moving.
“Window Seat,” Cuchulain
I’d only include my own song on this list if I meant it. This is the title track off my album of love songs, Window Seat, out on Valentine’s Day. The band will interpret it at Wildish Theater on Feb. 22. The show is 7 pm to 9 pm, info and tickets at WildishTheater.com.
“Oregon,” Sam Weber
A love song to our great state. I’d recommend a full listen of the whole album Clear and Plain from this Portland-based multi-instrumentalist. This song and “Void” are my favorites, but the feeling of this whole album is very wistful and romantic.
“Heart Tattoo,” Jenner Fox
Can heartbreak sound uplifting? The answer here is resoundingly yes. A tattoo of a heart, a remnant of a love gone wrong. Make it anything else: a whale, the Liberty Bell, anything. That’s where this soaring acoustic tune starts, featuring some of my favorite instrumentalists in the PNW backing the masterfully understated Bellingham-based songwriter.
“Right On,” Humbird
The title track of this Minnesota band’s 2024 album hits you square in the chest. I introduced them at the Sisters Folk Festival and was blown away by the lead singer Siri Undlin’s presence and voice. This whole album is magnificent, recorded live to tape. They’re performing at the Hybrid Gallery on Friday, April 4, admission is $17.50. Tickets and info at TheHybridEugene.com.
“All In Good Time,” Iron & Wine featuring Fiona Apple — tied for second
If you’ve made it this far, congratulations — these last three songs absolutely blew me away. This lilting duet communicates a complicated past love in the most tender way. I listened to it on an especially romantic drive with my wife and I’ll never be able to untangle this song from that.
“II MOST WANTED,” Beyoncé featuring Miley Cyrus — tied for second
For lovers of country, cars and insane vocal performances. My wife and I sang this at a friend’s wedding on Memorial Day weekend last year, and now I get a little teary-eyed every time I hear the line “I’ll be your shotgun rider, til the day I die.”
“Right Back To It,” Waxahatchee featuring MJ Lenderman
My favorite love song of the past year is also my favorite overall song of the past year. These artists both toured through Portland in 2024, and I think this track captured so beautifully the push and pull of a yearslong love. The relaxed banjo, the dance of the duetting vocals on the chorus, the comfortable tempo — I can’t stop listening.