Bob Dylan was tired. It was June 1965, and the man who had supposedly "saved" folk music was currently busy killing his image as a protest singer. He sat in Columbia’s Studio A in New York City, surrounded by a group of musicians who weren't entirely sure what he wanted. Among them was Mike Bloomfield, a guitarist whose blues licks would eventually define an era. They were working on a track that didn't even have its final name yet. It was called "Phantom Comes Back" on the session sheets. Eventually, it became It Takes a Lot to Laugh, It Takes a Train to Cry, one of the most laid-back yet emotionally heavy tracks on the seminal Highway 61 Revisited album.
Music is weird like that.
Sometimes a song isn't about the lyrics. Sometimes it's about a specific groove or a feeling of exhaustion that translates perfectly through a piano riff. For Dylan, this track represented a massive shift. He was moving away from the acoustic "finger-pointing" songs of his early twenties and leaning into a surrealist, electric blues sound that confused half his audience and exhilarated the other half. It’s a song about movement, frustration, and the weird juxtaposition of humor and despair.
The Messy Birth of a Classic
Most people don't realize how close this song came to being a fast, frantic rocker. If you listen to the early takes—specifically the ones found on The Bootleg Series Vol. 12: The Cutting Edge—the tempo is blistering. It sounds like a nervous breakdown. Dylan is shouting over a driving beat, trying to force the song into a shape that just didn't fit. It was frantic. It was messy. It was honestly a bit of a headache.
Then something clicked.
They slowed it down. They let the shuffle breathe. By the time they hit "Take 9" on June 29, the song had transformed into the sultry, late-night blues shuffle we know today. Paul Griffin’s piano playing became the heartbeat of the track. It’s a swampy, rolling sound that feels like a train chugging along a track at 3:00 AM.
The title itself is a mouthful. It Takes a Lot to Laugh, It Takes a Train to Cry is a phrase that Dylan likely cobbled together from various blues tropes and his own abstract thoughts. It doesn't appear in the lyrics. Not once. He does that a lot. It’s a move borrowed from the old-school bluesmen who would title a song based on a vibe rather than a chorus.
What’s Actually Happening in the Lyrics?
If you try to map out a narrative in this song, you’re going to have a bad time. Dylan isn't telling a story with a beginning, middle, and end. He’s painting a scene. He’s the "mailman" who brings no mail. He’s "on the ship" while it’s sinking. He’s looking for a woman who can "help him tell right from wrong."
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It’s about being stuck.
Despite all the imagery of trains, ships, and planes, the narrator is emotionally paralyzed. There’s a profound sense of loneliness masked by the jaunty rhythm of the music. When he sings, "I wanna be your lover, baby, I don't wanna be your boss," he’s stripping away the power dynamics that usually defined 1960s pop songs. He's asking for a connection that he clearly isn't finding.
The Mike Bloomfield Factor
We have to talk about Mike Bloomfield. If Dylan was the brain of Highway 61 Revisited, Bloomfield was the nerve endings. His guitar work on It Takes a Lot to Laugh, It Takes a Train to Cry is a masterclass in restraint.
He wasn't playing "at" the song. He was playing with it.
Bloomfield was a white kid from Chicago who had spent his youth sneaking into South Side blues clubs to learn from legends like Muddy Waters and Howlin' Wolf. He brought an authenticity to Dylan’s electric period that saved it from sounding like a gimmick. In this specific track, his fills are sharp and stinging, cutting through the warm bed of the organ and piano. It’s the sound of a man who understands that in blues, the notes you don't play are just as important as the ones you do.
Why the "Train" Imagery Matters
Trains are the oldest trope in the book. From Johnny Cash to Robert Johnson, the locomotive has always symbolized freedom, escape, or the inevitable march of time. But Dylan flips it. In this song, the train isn't a way out. It’s the thing that makes you cry.
It’s the sound of distance.
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When you hear a train whistle in the distance, it reminds you of everywhere you aren't. Dylan taps into that universal melancholy. He’s sitting on a hill, watching the moon, waiting for something that probably isn't coming. It’s incredibly relatable even if the specific lines about "donkey beads" and "brakemen" feel like they belong in a fever dream.
Misconceptions About the Highway 61 Sessions
A lot of rock historians like to pretend these sessions were some kind of mystical, effortless occurrence. They weren't. They were chaotic. Dylan was notoriously difficult to follow. He would change keys without telling anyone. He would change the lyrics between every take.
Producer Bob Johnston deserves a lot of credit for just keeping the tapes rolling.
In the case of It Takes a Lot to Laugh, It Takes a Train to Cry, the struggle was finding the right "swing." The 1960s were dominated by the 4/4 backbeat of the British Invasion, but Dylan wanted something older. He wanted the "thin, wild mercury sound." This track is the closest he ever got to pure, unadulterated American blues, filtered through a mid-sixties Greenwich Village consciousness.
- The Tempo Shift: The decision to slow the song down changed the entire meaning of the lyrics.
- The Instrumentation: Using a barrelhouse piano style gave it a timeless, dusty feel.
- The Vocal Delivery: Dylan sounds genuinely tired here, which works perfectly for a song about the weight of laughter and tears.
The Legacy of a "Minor" Masterpiece
Is this Dylan's most famous song? No. "Like a Rolling Stone" usually takes that crown. But for many hardcore fans and musicians, this is the track they go back to.
It has been covered by everyone. Al Kooper and Stephen Stills did a sprawling version on Super Session. The Grateful Dead turned it into a staple of their live shows, often stretching the shuffle out into a ten-minute jam. Jerry Garcia’s soulful, high-register vocals actually fit the "cry" element of the song perhaps even better than Dylan's original snarl.
Even The Allman Brothers Band found something in it. Why? Because the "bones" of the song are so strong. You can play it as a folk song, a rock anthem, or a slow-burn blues number, and it still works. That is the hallmark of truly great writing.
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What We Get Wrong About Dylan’s Blues
The biggest mistake people make is thinking Dylan was "parodying" the blues. He wasn't. He was obsessed with it. He spent his early years in Minnesota listening to the high-wattage radio stations coming out of Shreveport and New Orleans.
It Takes a Lot to Laugh, It Takes a Train to Cry is an homage.
But it’s a modern one. He took the structure of a standard 12-bar blues (sorta) and injected it with the surrealist poetry of the Beats. He proved that you didn't have to be a sharecropper in the Delta to understand the fundamental human urge to "lay down your weary tune."
How to Listen to It Today
If you want to actually appreciate this song, don't listen to it on tinny laptop speakers. Put on a good pair of headphones or crank it up in a car. You need to hear the separation between the instruments. Listen to the way the bass interacts with the piano.
Notice the "huff" in Dylan's voice.
By the time he gets to the final verse—the one about the moon being over the hill—the music has built into this incredible, rolling momentum. It feels like the world is moving, even if the narrator is standing still. It’s a masterclass in atmosphere.
Actionable Insights for the Dylan-Curious
If this song resonates with you, there are a few specific things you can do to deepen your understanding of this era of music history:
- Compare the Takes: Go to a streaming service and find The Cutting Edge 1965-1966: The Bootleg Series, Vol. 12. Listen to "Take 1" of this song (the fast version) and then immediately jump to the final album version. It’s the best way to see how a song "finds itself."
- Trace the Influence: Listen to the Grateful Dead’s version from San Francisco '76. It shows how the song evolved from a studio experiment into a piece of living, breathing improvisational music.
- Read the Context: Pick up a copy of Behind the Shades by Clinton Heylin. It’s widely considered the definitive account of Dylan’s recording processes and explains the tension in the studio during the Highway 61 sessions.
- Look for the Patterns: Notice how Dylan uses "movement" (trains, ships, walking) to describe emotional states. It’s a trick he’s used for sixty years, but it arguably started right here.
Music isn't just about melody. It's about the space between the notes. This song occupies that space perfectly. It’s a reminder that sometimes, the only way to deal with the absurdity of life is to find something to laugh about, even when everything around you makes you want to hop a train and disappear.