Ah, it’s that magical time of the year again. Spring is on the horizon, a bunch of weird old guys in ridiculous hats checked to see if a groundhog saw its shadow, and love is in the air for Valentine’s Day.
I’m no Valentine’s Day hater. When it comes to love, appreciation, and fancy dinners, you can always count me in.
But there is a shadow side to the celebration. If you’re single – or even worse, if you’ve recently had your heart broken – Valentine’s Day is sometimes just a little tough.
This mix tape is not meant for wallowing, or to hate on a so-called “Hallmark holiday.” It’s simply an acknowledgment – and even a reverent celebration? – of the shadow side of love.
And life.
Life is always kinda tough, but it especially is right now. Every good mix tape has a few layers or angles, and for this one I’ve chosen – or it has chosen, as mix tapes often seem to create themselves – to focus on the line between being brokenhearted and exhausted by life.
Musically, this mix tape leans largely on classic rock and Americana. The core of it is three “double shots” from Jay Bennett and Wilco, Tom Petty, and Bill Mallonee’s criminally underappreciated band the Vigilantes of Love.
I typically try to avoid repeating bands too much on a mix tape, but like the best mix tapes, this one kinda took on a mind of its own, so I had no choice but to go with it.
ONLY A BROKEN HEART: A MIX TAPE
TRACK ONE: “So Lonely,” by the Police
From: 1978’s Outlandos d’Amour
Somewhat surprisingly, one of the best break-up songs of the ‘70s was written by Sting (for another surprising entry to this list, see track eight). The entire lyric oozes heartbreak, which interestingly contrasts its upbeat, faux-reggae feel.
The lovingly janky guitar solo, which even comes in a little early, fits the theme of brokenness, while Sting’s bass part during it has a practically deranged energy. And is that a harmonica randomly thrown in for like two measures? Weird, but awesome.
Lyric to break your heart: Now no one’s knocked upon my door / for a thousand years or more / all made up and nowhere to go / welcome to this one man show / just take a seat they’re always free / no surprise, no mystery / in this theater that I call my soul / I always play the starring role
TRACK TWO: “Shakin’ Sugar,” by Jay Bennett and Ed Burch
From: 2002’s The Palace at 4 A.M. (Part I)
The next two tracks stem from perhaps Wilco’s second or third best album – although it’s never been released.
Between 1997’s power pop Summerteeth and the deconstructed indie folk of heralded Yankee Hotel Foxtrot, the band recorded almost an entire album’s worth of demos that stand up well with both of those records. Some material from these sessions have been released, though, including this track from ex-Wilco member Jay Bennett (RIP).
The jangly sadness of “Shakin’ Sugar” – or “Alone,” as it was called during those sessions – is given the full wall-of-sound treatment from the Yankee Hotel Foxtrot mastermind. Layers and layers of guitars and keyboards make for an always-interesting listen. The deceptively simple lyrics reveal how sad ordinary things and activities seem to be at the depths of loneliness. “Alone, alone, alone,” indeed.
Lyric that’ll break your heart: I feel like a book, but I just can’t start it / feel like a lover, brokenhearted / I look in the mirror at the face in the glass / I look like a question no one ever asked / alone / like I’m supposed to be
TRACK THREE: “Magazine Called Sunset,” by Wilco
From: 2003’s More Like the Moon EP, and the compilation Alpha Mike Foxtrot: Rare Tracks 1994-2014
If Summerteeth and Yankee Hotel Foxtrot had a baby, it’d be “Magazine Called Sunset,” although the same could be said for most of the songs recorded between the two albums. It has the power pop feel of the former with the deconstructed/weird sounding vibe of the latter. Typically for Jeff Tweedy (especially from this era), the lyrics are somewhat opaque, although the “lyric that’ll break your heart” is enough to qualify it for this mixtape.
Lyric that’ll break your heart: There’s a magazine called Sunset / and a tape machine that won’t let / me ever forget this impossible longing for you
TRACK FOUR: “Climb That Hill,” by Tom Petty
From: 1996’s She’s the One, and the 2020 re-issue Wildflowers and All the Rest
Tom Petty’s 1994 album Wildflowers, and its 1996 follow-up She’s the One, were written as Petty’s marriage was dissolving. As such, there is a lot of material that could fit on this mixtape, but “Climb That Hill” works especially well because it has a somewhat hopeful message of resilience. We don’t want to wallow now, do we?
Already a heavy, riff-led track, the version of “Climb That Hill” on the newly released Wildflowers and All the Rest is more uninhibited than the original from She’s the One. The “lyrics that’ll break your heart” is one of my favorites of all-time. You might be able to relate to it as well.
Lyric that’ll break your heart: Little Lucy’s such a doll / I’d like to climb her garden wall / but she only sees me as a friend / I have to get up/and climb that hill again
TRACK FIVE: “Confusion Wheel,” by Tom Petty
From: 2020’s Wildflowers and All the Rest
Okay, so maybe we need a little bit of wallowing? But only when it’s this damn devastating. Petty describes loneliness in such a stark way that it was possibly too personal for him to want to release, as it sat on the shelf for almost 20 years. Quality-wise, though, this sadly lilting ballad stands with anything on Wildflowers.
Lyric that’ll break your heart: So much confusion has entered my life / so much confusion goes ’round in my brain / so much confusion has torn me apart / and I don’t know how to love / and I don’t know who to trust / and I don’t know why that is
TRACK SIX: “Welcome to Struggleville,” by Vigilantes of Love
From: 1994’s Welcome to Struggleville
Bill Mallonee, leader of the Vigilantes of Love, is one of the hardest-working men in songwriting. He comes out with an album almost every year, and the quality of his work has only gotten stronger since his flirtation with alt-rock / alternative-country stardom in the ‘90s.
Vigilantes of Love’s reputation first began to rise with 1994’s Welcome to Struggleville and 1995’s Blister Soul. The darkly jangly title track from the former explores the deeper, interior side of loneliness and despair. Some might call it existential dread. Its malaise fit 2020 so well that John Mellencamp covered it.
Lyric that’ll break your heart: I’ve been trying to negotiate peace with my own existence / she’s got a stockpile full of weaponry / she’s breaking every cease-fire agreement / now the whole thing is full of decay / as sure as I’m made of dust/and into rust I know the beast is falling
TRACK SEVEN: “Blister Soul,” by Vigilantes of Love
From: 1995’s Blister Soul
Mallonee has often looked to the Dust Bowl desolation of John Steinbeck (remember Grapes of Wrath and Of Mice and Men from high-school English class?) and Woody Guthrie for lyrical inspiration. “Blister Soul” is a good example of that. It’s rare to find lyrics with this sort of psychological depth combined with such a catchy melody and feel.
Lyric that’ll break your heart: Said you woke up this morning / said you woke up under a curse / I’ve heard the blues are bad but this is something worse / and the ambulance driver/well he tips his hat and stares / and he asks you in a grave voice, “Can I take you anywhere?” / yeah, it’s the thing we cannot speak of / too painful to behold / this blister soul
TRACK EIGHT: “Dancing in the Dark,” by Bruce Springsteen
From: 1984’s Born in the USA
Rage Against the Machine’s Tom Morello, an occasional Springsteen collaborator, turned me on to just how dark “Dancing in the Dark” is. Yes, that “Dancing in the Dark.” The one with dated ’80s production and a video featuring Springsteen dancing embarrassingly with Courtney Cox.
Morello was getting some heat on Twitter for working with the Boss. (Evidently, he’s too mellow for some Rage fans.) Morello responded by noting that the lyrics for “Dancing in the Dark” are darker than anything Iron Maiden ever did.
I was skeptical, but damn, he’s right. Bruce makes self-loathing fashionable sounding on this mega hit, but every line is crushing. You can feel the despair in lines like “want to change my clothes, my hair, my face!”
Lyric that’ll break your heart: Message keeps getting clearer / radio’s on and I’m moving around the place / I check my look in the mirror / I want to change my clothes, my hair, my face / man, I ain’t getting nowhere / I’m just living in a dump like this / there’s something happening somewhere / baby, I just don’t know where it is
TRACK NINE: “Someday Never Comes,” by Creedence Clearwater Revival
From: 1970’s Mardi Gras
CCR’s John Fogerty isn’t exactly known for his ballads, although there is that side to him (“Long as I Can See the Light,” “Lodi”). He’s at his saddest and most affecting on “Someday Never Comes.” Like “Dancing in the Dark,” Fogerty makes you feel the despair, especially in the chorus. The instrumentation is oh-so-very classic rock in my favorite sort of way – guitars, bass, drums, a bit of piano and organ for flavor. There’s even a key change!
Lyric that’ll break your heart: First thing I remember / was asking papa “why?” / ’cuz there were many things I didn’t know / and daddy always smiled/took me by the hand / saying, “someday you’ll understand” / well I’m here to tell you now, each and every mother’s son / you better learn it fast/you better learn it young / ’cuz someday never comes
TRACK TEN: “Burning the Midnight Lamp,” by Jimi Hendrix
From: 1968’s Electric Ladyland
The final track on this mixtape – and it definitely has that “final song” feel, doesn’t it? – is one of Jimi Hendrix’s “lost singles.” I say “lost” because classic rock radio, which used to have it in their rotation, has now basically completely abandoned the song.
It’s too bad, because “Burning of the Midnight Lamp” might be the greatest psychedelic rock song of all time, and the best example of Hendrix’s sometimes underrated strengths as a songwriter. Its complicated-but-simple sounding riff is one of his best (and is super fun to play on guitar). The reason it works so well as a psychedelic song is because it has that trippy feel without overdoing it.
The lyrics also have more depth than a typical track in that genre. It’s a good way to end this mix tape, as it gets to the heart of sadness (especially when he mournfully sings “loneliness is such a … draaaaaag) while also giving an antidote: focusing on work, burning the midnight lamp.
Lyric that’ll break your heart: The morning is dead / and the day is, too / there’s nothing left here to meet me / but the velvet moon / all my loneliness I have felt today / it’s like a little more than enough / to make a man throw himself away / and I continue/to burn the midnight lamp
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