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My Gen X Playlist: Sixth Avenue Heartache – The Wallflowers

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Are you a good judge of character?
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I grew up in the suburbs, in a bubble. When I moved to LA to attend college, it was eye opening to say the least. It was also new and exciting.

One weekend I ventured downtown. I wanted to wander around the city and soak up this new experience. I came upon a crowd congregating at the corner. I couldn’t help but check it out.

Everybody was watching a nice old man, sitting on a stool, shuffling three cards on a cardboard box. He would show us one card, the ace of hearts. He flipped it over and shuffled the three cards again. Our goal was to find the ace of hearts. Of course I thought this was easy. Three times in a row, I followed the card and guessed correctly. The nice old man smiled and complimented me profusely. He offered a small wager if I could guess it correctly again. Two words sounded in my head.

Easy money.

The thought of taking money from this nice old man did not seem fair. I actually felt bad before the shuffle. Of course, you know the rest. I think they should have tattooed the word “Sucker” across my forehead. Three card monte. Dumb.

Wandering around the city can’t be all bad. Jakob Dylan took to wandering the city early on his career and had a completely different experience. From his wanderings, he wrote Sixth Avenue Heartache.

Wallflowers lead singer Jakob Dylan wrote “Sixth Avenue Heartache” in 1988 when he was only 18 years old. He was living in New York City off of Sixth Avenue, having dropped out of the Parsons School of Design, where he studied painting, after just two weeks. Despite being the son of Bob Dylan, he was on his own, living by himself and spending a lot of time wandering around the city and contemplating his life. The lyric reflects images of the city and his search to find his path. This was when he decided to make music his life, or at least give it a shot.

– songfacts

Wandering the city gave me a twenty buck lesson on how naive I really was. I guess you can say my college education included an extracurricular class: Street Smarts 101. This was the first lesson of many living in the city.

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For a complete playlist, please click here.

For the Spotify playlist, please click here.

Sirens ring, the shots ring out
A stranger cries, screams out loud
I had my world strapped against my back
I held my hands, never knew how to act

And the same black line that was drawn on you
Was drawn on me
And now it's drawn me in
6th Avenue heartache

Below me was a homeless man
I'm singin' songs I knew complete
On the steps alone, his guitar in hand
It's fifty years, stood where he stands

Now walkin' home on those streets
The river winds move my feet
Subway steam, like silhouettes in dreams
They stood by me, just like moonbeams

Look out the window, down upon that street
And gone like a midnight was that man
But I see his six strings laid against that wall
And all his things, they all look so small
I got my fingers crossed on a shooting star
Just like me-just moved on

15 thoughts on “My Gen X Playlist: Sixth Avenue Heartache – The Wallflowers”

  2. Oh wow. I like that song and didn’t realize the singer was Bob Dylan’s son! You can hear the similarity when he lets a note kind of … trail off. So many of life’s hard lessons get learned in the big city. I remember taking the bus home from NYC coatless (and freezing) b/c I left my leather coat on a chair in a club.
    Great post!

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  4. i had the CD when it first came out. hard tellin’ where it’s at now?? i probably trashed it when i trashed 100s of CDs back in 2015. (i feel taken by the whole CD trend)

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  5. Idk i grew up in the city and never had a con happen on me…i have dealt with phony beggars who have signs that say they need food and then when I offer to buy them food they say just give me money instead. My wife is a very generous soul and has only recently wised up to this ruse someone asked for money and had a sign that said any amount is acceptable so she offered the man $5 but he insisted on $20

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    1. I’ve offered food as well and received angry responses. One time a homeless person just was straight with me. He wanted a couple of bucks to buy a drink. I was torn, but gave him a couple of bucks for his honesty. I’m not sure if that was the right choice, but oh well.

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  6. I spent, roughly, eight hours in Manhattan in 1991. That was enough. It was total culture shock. I’d never seen street vendors. I’d never seen a guy in a trench coat full of watches. I’d never seen cars up on blocks with wheels missing.

    I was raised in a small town (that has grown far too big for my taste, now). I live in a small town, now. I like it. Really big cities freak me out.

    I miss Jakob Dylan’s music on the radio.

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      1. I was standing at a street vendor, getting a hot dog (my first vendor food like that) and he walks up to me, opens his coat and watches are hanging everywhere. I declined and he politely walked away. It was bizarre to a small town person.

        I will say that, my visit to Macy’s HQ store and a run thru FAO Schwartz was fun. I was with a small group and a small bus had been charted for us for viewing the city. What we got was, a very small bus, with port-hole type windows. We could barely see anything. A tour guide at the front…I remember him saying “Look! It’s the Empire State Building! Look! It’s the Statue of Liberty! Look! There’s a Sears tower!.” No camera in that bus could have captured anything with those weird, little windows.

        The best part was the fly-out from LaGuardia. It was dusk and the city was lit up. It was beautiful from the sky.

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  7. Walking into a new big city is like walking into Narnia. You get so excited about the new adventure but you don’t know what’s waiting for you. I’ve been there too.

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