Objective standards exist that can help you make a judgment like that, but the answer also often involves intuitive leaps that defy logic or explanation; sometimes greatness is entirely subjective, residing in the way one particular line of a song hits you at one specific moment in your life. A great song might feature a brilliant lyric, or a captivating melodic hook, or an amazing solo, or all of the above, or none. But many if not most of them also manifest a certain je-ne-sais-quoi that elevates them by engaging your heart, your mind, your feet, or all of you at once.
The songs that follow below are more than just “deep tracks” from familiar artists, though; these songs are by acts you’ve likely never heard of, unless you’ve been cyber-stalking me. The chance of you ever having heard more than one of these individual songs is pretty low, and your chances of having heard all of them, nearly nonexistent. And yet, these are some of my favorite songs that I’ve discovered over the past 25 years while writing for the Daily Vault. Give them a shot and maybe you’ll catch a hint of the feelings that hit me when I heard each of them for the first time—the camera-flash of discovery, the supercharged sensation of being fully present and engaged, the giddy warmth of new love.
That’s the stuff; now go get some.
Last Charge Of The Light Horse – “This Is Where”
This list is organized alphabetically by artist except for the first and last entries, the only repeats by a single artist—because singer-songwriter Jean-Paul Vest and his group Last Charge Of The Light Horse delivered not one but two of my favorite songs of the last quarter century. On “This Is Where,” the intricate, surging opening dialogue between drums and guitar, a propulsive chorus, and Vest’s novelistic lyric about losing yourself in a moment deliver the kind of musical alchemy that can give you goosebumps just thinking about it.
Arms Of Kismet – “My Mercurial Nature”
Arms Of Kismet (and Waterslide) mastermind Mark Doyon often works in characters, and maybe this is one, too, but this soaring, idiosyncratic slice of thinking-man’s power-pop feels like one of his most revealing and self-aware numbers, and features—among other great lines—this remarkable sequence: “Where would I be without my anger / at a world that’s got to change? / Where would I be without these sins / made me who I am today?”
Ben Bostick – “Lucky Us”
How do we get through life when it begins to feel like there’s one roadblock after another in our path? One answer is gratitude. When we remember to appreciate the good things in our lives, the hurdles we must still face can begin to feel less daunting. A simple enough lesson that singer-songwriter Ben Bostick brings to vivid life in a gentle, lilting, devastatingly direct song that hits like a 20-pound sledgehammer.
Butchers Blind – “Black And White Dreams”
Before singer-songwriter Pete Mancini stepped out as a solo artist, he fronted the Long Island quartet Butchers Blind. For the group’s final 2015 EP A Place In America—a powerhouse swan song—Mancini penned this Springsteenesque anthem for the bruised and battered American dream, singing his heart out as the band surges behind him in one of their finest moments.
Stephie Coplan & The Pedestrians – “JERK!”
Is this tartly delivered, hook-laden concoction a novelty song, or dead serious? Was young Stephie Coplan dreaming of becoming the next Ben Folds, or the next Taylor Swift? If a songwriter delivers a song this potent and then abandons life as a musical performer for another field, do their songs still matter? The answer, on all counts, is “yes.”
Danelia Cotton – “It’s Only Life”
Singer-songwriter-guitarist Danelia Cotton melds heavy blues-rock with soul and gospel elements, never more effectively than on this number, whose skyscraping, indelible hook is a wordless gospel chorus counterpointing her passionate lead vocal. Magnificent.
Chris Cubeta – “Me And The Radio (acoustic)"
Songs about songs are tricky; it’s inevitably insular subject matter. But that feeling you get when a song you love comes on the radio (or pops up on shuffle) is universal, and here Chris Cubeta brings that sensation to technicolor life with a terrific lyric elevated further yet by a superb arrangement and committed performance.
Euphoria – “Back Against The Wall”
Flanged-out slide guitar, wailing harmonica, pulsing synths and booming electronic drums are not what I’d call an obvious combination. When Euphoria—a.k.a. songwriter/producer/multi-instrumentalist Ken Ramm—layers them all together, though, they add up to a compelling, cinemascope soundscape. (And in fact you may have heard Euphoria’s music without knowing it, as Ramm’s evocative tracks have been licensed frequently over the years.)
Casey Frazier – “Not A Whole Lot Going On”
Americana artist Casey Frazier names Garth Brooks as his musical idol, but there’s more than a little Muscle Shoals r&b in the bones of many of his songs. This finger-snapping paean to the simple joys of domestic life (“I’ve been asking for an enlightened revelation / When all along it was out there on my street”) features a punchy horn section that gives the song real swing and groove even as it’s counterbalanced by twangy slide guitar notes.
Max Gomez – “Rule The World”
Sometimes the best songs are so simple; all you really need is an acoustic guitar and the ability to turn your audience’s expectations inside out. The gently thrumming, beautifully sung “Rule The World” is in fact about the exact opposite of megalomania: a lover who would do anything to “take the pain from your heart / I would tear it all up, I’d tear it apart.” And when Gomez sings it, you believe he would.
Kimon Kirk – “Trampoline”
A great radio single usually features certain specific elements: an engaging vocal melody, a catchy instrumental hook, a memorable central idea or image, tight and seamless construction, and/or a distinct vibe. When a song features all of those elements at once—as on Kimon Kirk’s “Trampoline”—it can be something close to irresistible.
Jill Knight – “Jeans”
The oldest song on this list (1998) is among the best. Building off an elastic, funky groove, folk-rock singer-songwriter Knight’s rangy voice becomes more playful each time she circles back to the clever chorus: “Wear me like your favorite pair of jeans / We feel good on each other / Stitch me up mend me / When I'm falling apart at the / Seems like we belong together…” It’s an anthem for the frisky romantic in each of us.
Amy Lennard – “I Wish It Were Mine”
The structure of great songs is often deceptively simple; this one—a chiming, steady-building number about longing for what you don’t have—rests on the conceit that each verse/chorus segment ends with a twist. The risk is that if a single one of these transitions failed to hit the target, the whole construction might collapse. Needless to say, each one comes up a bullseye on this song, “a rich, subtle brew of good intentions and green-eyed undercurrents.”
Jeremy Nail – “My Mountain”
The struggle every songwriter faces in writing about their own lives is to make the personal universal. Here Jeremy Nail takes a deeply personal setback—the amputation of his left leg due to cancer—and turns it into art. Building off a smoldering backbeat that feels like it was born in a cave somewhere east of Memphis, the riveting “My Mountain” employs metaphor to make Nail’s struggle to learn to walk again into a shared experience (“My mountain, the story of our age / There’s always something standing in our way”).
The Tom Collins – “Why Don’t You Leave” / “That Town You Love”
I nearly chose the spectacularly hooky kickoff cut “Back Of Your Mind” from this album-long “Tom Petty plays Led Zeppelin” fantasia, but this two-part suite has even greater impact. After “Why Don’t You Leave” establishes singer/songwriter/guitarist Fran Capitinelli’s bona fides with a keening acoustic showcase, “That Town You Love” brings the hammer down with “Immigrant Song”-adjacent electric thunder.
Jon Troast – “What We Become”
Earnest folk-rock songsmith Troast bumps up both the tempo and the wordplay on this warm and witty number about how we’re all mothers and fathers and daughters and sons, living inside a pattern that both repeats and evolves. Turning penetrating insights into chuckle-worthy one-liners is a skill in and of itself; setting it to an ebullient acoustic-funk arrangement is the cherry on top.
Becky Warren – “We’re All We Got”
One of my favorite discoveries of recent years, Becky Warren combines the heart of a poet with the muscle and sass of a rock and roller. Her 2018 album Undesirable found her writing songs in the voices of homeless people she met on the streets of Nashville. The ringing, hooky “We’re All We’ve Got” feels like a Tom Petty anthem with a silvery undercurrent of despair, a barroom singalong for people with nowhere else to go.
Last Charge Of The Light Horse – “What If”
“What if we didn’t punish ourselves / For what we’re not? / Stopped wishing for some other heaven / Than the one we’ve got?” A flat-out stunner, “What If” is a rumination on possibility and remembering how to be happy, set to gorgeous chiming guitars. “Light from the ground throws our shadows on the blue,” Vest sings as the music surges, “turns the world upside down and I remember how to love you.” Chicken skin, every time.