We’ve decided to make our guest playlists a regular feature of the blog, and to kick off that series — or to continue the one we ran leading up to the release of our 33 1/3 volumes — we turn to an alum of a prototype for our Writing New York course. In the fall of 2001, one of the first two courses I taught at NYU was a small honors seminar called “New York Writing,” which contained a decent amount of material that would eventually wind up in the course Cyrus and I would launch together a couple years later.

Nicholas Taylor is an editor and writer from Long Island, now living in Seattle. I advised his undergraduate thesis at NYU on Andy Warhol, the Velvet Underground, and the downtown 1960s NYC scene. He has also written on music and culture for Pop Matters, the Park Slope Reader, New York Spirit, and Cinemit. Find out more here.

Lou Reed is the James Joyce of New York. It seems he has made it his life’s work to understand this place that defies understanding, to provide snapshots of meaning in a place that often feels both meaningless and too full of meaning. From what brings outsiders to the city to the challenges and enticements encountered there, Reed’s work covers the gamut of the NYC experience.

“Smalltown,” by Lou Reed and John Cale, from Songs for Drella (1990). This tale of Andy Warhol’s odyssey from Pittsburgh to New York beautifully captures what draws creative misfits from all over the world to New York. Here he focuses not so much on the greatness of the city but rather on the suffocating dreariness of the small towns that people leave. “I hate being odd in a small town / if they stare let them stare in New York City / at this pink eyed painting albino / how far can my fantasy go?”

“Rock and Roll,” by Lou Reed, from the live album Rock and Roll Animal (1974). The more optimistic version of the coming to New York story. Jenny isn’t persecuted and shunned like the gay Warhol in the Rust Belt; rather, she’s suffering from your more run of the mill suburban ennui. Here, New York, as the source of the rock and roll music she hears on the radio, is her Emerald City, the shining jewel on the horizon that promises something better. She’s not seeking home so much as heaven. “Then one fine mornin’ she puts on a New York station / she couldn’t believe what she heard at all / she started dancin’ to that fine fine music / you know her life was saved by rock and roll.”

“Sheltered Life,” by the Velvet Underground, demo recording from the Peel Slowly and See box set (1995). Another version of Jenny and Andy, this time more whimsical and innocent, romanticizing all the experiences one can have in the big city. As a fellow Long Island to New York transplant, I know exactly where he’s coming from. “Never walked about on the streets at night / never got into an uptown fight / never smoked a hookah, never saw a rug / couldn’t even squash a beetle bug. . . . I know it’s true, / guess I’ve lived a sheltered life.”

“I’m Waiting for the Man,” by the Velvet Underground and Nico, from The Velvet Underground and Nico (1967). . This is where the sheltered life starts to not look so bad. In this reinterpretation of the classic flâneur narrative, Reed pulls back the curtain, taking us on a voyeuristic tour of the city’s seedier side. Notice how the song’s rhythm mimics the subway train this neophyte would surely have taken up to Harlem to score drugs. “I’m waiting for my man / twenty-six dollars in my hand / up to Lexington, 125 / feel sick and dirty, more dead than alive.”

“Walk on the Wild Side,” by Lou Reed, from Transformer (1972). In his quintessential song, Reed paints a portrait of the Warhol Factory scene as a bunch of Jenny’s and Andy’s—they’re drawn the city by the desire for freedom and excitement, which they get, though they also experience a lot that’s not in the brochure, as it were. Reed positions the city’s allure as a siren song, enticing outcasts from all over the world, though the they may not like what they actually find. “Candy came from out on the Island / in the backroom she was everybody’s darling / but she never lost her head / even when she was giving head / she said, “Hey babe, take a walk on the wild side.”

“Street Hassle,” by Lou Reed, from Street Hassle (1978). Reed comes full circle. He’s no longer focused on why out-of-towners come to New York, but rather just on what happens to them once they’re there. Even though this song is gruesome, the elegiac beauty of the music makes me think this is no morality tale. Instead of passing judgment of these denizens of the night, Reed finds the grace and drama of all the ways of life New York offers—even the ones most of us would probably rather avoid. “But why don’t you grab your old lady by the feet / and just lay her out in the darkest street / and by morning, she’s just another hit and run / you know, some people got no choice / and they can never even find a voice to talk with that they can even call their own.”

What’s on your NYC playlist?