10 Ryan Adams Songs that Nail Heartbreak

Whether you’re freshly entangled in the feelings following a soured romance, or you’re a few months out and still experiencing occasional pangs, heartbreak is a hard emotion to grapple with. Singer-songwriters excel at tapping into the human condition, especially when it comes to heartbreak. It seems like half the songs out there are about love gone wrong. Prolific songwriter Ryan Adams, known for his personal and self-reflective style, has penned his fair share of gut-punch songs that exemplify heartbreak. His aren’t songs aren’t strictly about love lost; he runs the gamut of heartbreak. Here are ten songs in which Ryan Adams nails what it means to have a broken heart.

1. “Meadowlake Street” – Cold Roses
Sometimes life interferes with a budding relationship, leaving a trail of “what if’s” in its wake. Adams spends “Meadowlake Street” remembering a relationship interrupted before it really began. Softly sung verses against a low guitar reveal a sweet almost schoolboy crush: “I used to be the house that you lived in down on Meadowlake Street/ When you moved they cut down the maple tree I carved your name into.” The guitar grows more agitated with the chorus; its plucking underscores the growing tension surrounding the song’s central question: “If loving you’s a dream that’s not worth having/ Then why do I dream of you? Why do I dream of you?” What could be a melancholic song switches pace near the three-minute mark with a sharp electric lead guitar and a romping drumbeat, both of which build towards a meaningful crescendo.

2. “Do I Wait” – Ashes and Fire
The song’s sorrowful first two bars feature a lone acoustic guitar before Adams’ vocals pose the question a relationship faces when it becomes one person’s investment rather than a shared effort. “Do I wait here forever for you?” he asks. An organ lingers in the background, barely audible over the guitar and drums, before becoming more prominent as the song aptly builds towards its emotional peak. As the song nears its midway point, a wailing electric guitar takes over, every emotional note it screams standing in for Adam’s lyrical silence. The song is built around power chords, which mirror the situation’s powerful emotional build-up wondering how long exactly do you wait for someone to care.

3. “Come Pick Me Up” – Heartbreaker
Arguably one of Adams’ most powerful songs about messy love, the harmonica and drumbeat in the opening bars set the stage for a heartfelt confession about one person’s power over another. With a voice that sounds almost slightly dazed, Adams pleads to spend more time with someone, even if that time may be destructive for both parties. It’s the last verse in particular that reveals the pain of holding onto a poisonous relationship, knowing full well it will hurt but yet unable to walk away: “I wish you’d make up my bed/ So I could make up my mind/ Try it for sleeping instead/ Maybe you’ll rest sometime/ I wish I could.”

4. “When the Stars Go Blue” – Gold
As if a breakup isn’t hard enough to survive, watching your now-ex significant other move onto a new relationship can bring with it pain equal to the original loss. Adams encapsulates that feeling opening “When the Stars Go Blue” with vocals alone before slowly adding in harmony and drums. The effect has a resigned feel about it, as the singer contemplates a person still incredibly important to him, but one who has redirected her attention elsewhere. With instrumental bridges that rely on Adams’ guitar, the song has a slow-dance feel, but a dance Adams has with his memories and not with his former lover.

5. “Am I Safe” – Ryan Adams
In one of the more non-traditional heartbreak songs Adams has penned, he contemplates the aftermath of falling out of love. It’s not a matter of surviving the breakup, but about being able to look himself in the eye after letting someone good go. Detailing dark thoughts and impulses he’s followed before, Adams sings “All these things keep running through my mind/ Everyone and everything I left behind.” A driving guitar rhythm leads right into a chorus built around the repeated question, “Am I safe? Am I safe? Am I safe? Am I safe?/ If I don’t wanna be with you.” It’s a fixation punctuated by a haunting harmony floating in the background, as if the past follows his every step.

6. “I See Monsters” – Love is Hell
The self-destructive tendencies Adams feels he brings to love here come across in the vivid imagery he uses to describe a relationship’s impending doom. While his partner lies next to him sleeping, he imagines her dreaming beautiful things that he will only taint: “Colors inside your head go spinning around/ Like a Ferris wheel/ Exploding and falling to the ground.” Adams picks up on this very theme in “Shadows” off his 2014 self-titled album. There, even from the vantage point of a relationship’s beginning, he can already see its end approaching. “I See Monsters” is a softer song coming at the end of an album rife with love’s every trouble, but its sharp and minor chords lend it an air of heartbreak on the horizon.

7. “Dear Chicago” – Demolition
Stripped down to a guitar and vocals, “Dear Chicago” embodies one of Adams’ more simple songs. The barebones backing emphasizes his lyrics, “I think about you all the time/ It’s strange and hard to deal/ I think about you lying there/ And those blankets lie so still.” It’s a moment long after a relationship has ended when the ghosts still haven’t cleared the room; they’re starting to fade, but not quite gone. Laced with a shimmering melody played via acoustic guitar and featuring a more up-tempo rhythm than some of his other melancholic songs, “Dear Chicago” somehow seems the sadder for its pace. Adams moves on to the future, but it almost seems against his will.

8. “This House is Not for Sale” – Love is Hell
From Adams’ first guitar strum, the syncopated rhythm reveals a fractured relationship at the heart of the song. The first lyrics, “Tell ‘em that the house is not for sale/ We’re still livin’ here, how come nobody can tell?” touch on attempting, but failing, to make a relationship work. Sweet memories of “dancing across the wooden floor” turn into something darker, and life finally threatens to undo all they’ve built together, physically and emotionally. The chorus, a repeated and insistent “Calm down,” grows to a howl by the song’s end, as Adams can’t keep things from spinning out of control.

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9. “Two” – Easy Tiger
“Two” has an easy country rhythm with a soft slide guitar in the background. The almost happy melody and rhythm juxtapose the pleading opening verse, “If you take me back/ Back to your place/ I’ll try not to bother you, I promise.” After emerging from a failed relationship, Adams realizes, “It takes two when it used to take one.” But, like so many other of his songs, he knows that he doesn’t have what it takes to make something last: “I got a really good heart/ I just can’t catch a break/ If I could, I’d treat you like you wanted me to, I promise.” The song’s steady energy contrasts the exhaustion the lyrics convey. Having realized what a relationship can offer, he can’t go back to living life by himself, and yet he must. For now.

10. “Do You Laugh When You Lie?” – Do You Laugh When You Lie EP
Many of Adams’ songs pertain to a reflective sense of heartbreak, but with “Do You Laugh When You Lie?” he goes the accusatory route. The song’s up-beat tempo, forceful drum beat and electric guitar creating a more emotionally charged experience than other songs on this list. Released in 2014 on the EP by the same name, the song repeats the chorus over and over again, the singer hypnotized by his lover’s betrayal and disregard for anyone other than herself. “It’s just my life!” he answers in response to his own question. The song’s on the shorter side at 2:27, but it’s heavy with an almost-gritty electric feel.