Intriguing both bibliophiles and music geeks in one gesture, the New York Public Library recently established a Lou Reed archive that makes accessible hundreds of hours of the man’s labyrinthine audio and video recordings, many photographs taken of and by Reed himself, press clippings from his notorious concerts, artwork, and selections from his personal papers. For those (like me) who insist on giving the best of rock lyrics the same respect as literature, seeing Reed’s personal archive get the same rollout that acclaimed writers such as John Updike or Toni Morrison might receive is pretty exciting. And there’s no better place than the NYPL to give a proud New Yorker like Reed—who made a long career out of writing about the city’s strange, eccentric, and marginalized—this kind of attention. The bleary, blurry image emblazoned on the limited-edition library cards are taken from Mick Rock’s iconic cover shot for Transformer, arguably Reed’s most popular solo record. It’s a creative way of bridging the gap between the bookshelves and the streets, which is a natural space for Reed’s work to live.

What made Reed’s songs special went beyond his notorious obsession with decadence, his caustic dry wit, and his sneaky romantic vulnerability. He was also one of the most literate of musicians and wasn’t shy about making his literary influences known. As a college kid, he was mentored by the brilliantly mad poet and critic Delmore Schwartz and took inspiration from the likes of Raymond Chandler, William S. Burroughs, James Joyce, Shakespeare, and Poe. Lulu, his odd later-period collaboration with Metallica, is perhaps best passed over—but basing a metal record on a 19th-century Austrian play is something very few writers would have even imagined, let alone attempted. Reed brought an informed, sophisticated writer’s eye to the kinds of underworlds he inhabited and observed, and his sense of language was as keen as a journalist’s. Reed made sure all the who, where, what, how, why bases got covered, using his own laconic, inimitable language.

Below is a mixtape-style selection of a few of his most literate and literarily engaging songs. As the man himself put it, between thought and expression lies a lifetime. Here’s a sample of what went into that lifetime.

1. “I’m Waiting for the Man”

Never has an anecdote about heading uptown to cop some dope been this Hemingway-esque. It’s all in the extremely sparse but very detailed language, incorporating the random snippets of street talk (“hey white boy, what you doin’ uptown?”) and the time-honored truisms of the drug game (“he’s never early, he’s always late/first thing you learn is that you always gotta wait”). The way the half-spoke, half-sung lyrics change the article in the title—“waiting for MY man” rather than just “THE” man—adds a bit of a homoerotic overtone, which make the song even more narratively complex for the mid ‘60s.

2. “Heroin”

Probably The Velvet Underground’s single greatest song, and one that Reed would revisit at various points in his career. Everything that made the band revolutionary comes together, lyrically and musically. From the forlorn thesis statement in the opening—“I don’t know just where I’m going/ But I’m/ Gonna try for the kingdom if I can”—about escaping the ugly realities of urban life “where a man cannot be free/ of all of the evils of his town/ and of himself and those around” to the dreamlike fantasies that intoxication brings: “I wish that/ I’d sailed the darkened seas/on a great big clipper ship.” The song’s hypnotic melody and propulsive rhythm immerse the listener in an experience that has rarely been produced in pop music, then or now.

3. “The Gift”

What other band would set an entire short story to music? This darkly funny little anecdote of long-distance romance gone awry is one of the hidden gems of White Light/White Heat, the band’s pitch-black second record. It’s a short story Reed wrote as a creative writing student in college. Lovelorn Waldo Jeffers longs for Marsha, his sort-of girlfriend during a break from school. Tortured by his visions of her falling for someone else, Waldo takes unexpectedly drastic measures to surprise her. John Cale reads the story in his lovely Welsh voice in one stereo channel while the band grooves away in the other. And lucky for us: we now have clearer recordings to help make this mash-up work.

4. “Candy Says”

One of Reed’s unique skills as a songwriter was being able to create a fully-fleshed character within mere minutes. This opening track to the band’s third record is one of his most poignant. Inspired by one of Warhol’s superstars—also referenced by name in “Walk On the Wild Side” as the one who hails from “the islands” and doesn’t lose her head even when…you know the rest—it’s a song about the emotional quandary Candy finds herself in as a trans person in a world that won’t see or hear her on her own terms: as she explains by way of introduction: “I’ve come to hate my body/ And all that it requires from this world.” Velvet Underground member Doug Yule sings it with a touching innocence. Reed once generously described Candy’s state of mind in terms of the universal experience of not liking what one sees in the mirror: “I don’t know a person alive who doesn’t feel that way.” Here, he takes that emotion and applies it to someone whose whole life hangs in the balance.

5. “Pale Blue Eyes”

This is what I was talking about when I mentioned romantic vulnerability before. Reed always had attitude to burn, and he was infamous for being as surly and unforthcoming as possible in interviews. It’s fair to say that Reed kept his guard up as often as possible in public, though in his music it was sometimes a very different story. In terms of putting your still-beating heart out on a slab for all to see, this song is about as naked and vulnerable as it gets: “It was good what we did yesterday/ And I’d do it once again/ The fact that you are married/ Only proves you’re my best friend/ But it’s truly, truly a sin/ Linger on/ Your pale blue eyes.”

6. “Perfect Day”

Of course, pretty much everyone already knows this one. But instead of that being a reason for exclusion, I think it shows how universally relatable Reed’s writing could be. It was sung by a series of prominent musicians after Reed died and remains one of his most emotionally affecting songs. The beauty is in the simplicity: a walk in the park, a trip to the zoo, taking in a flick, and then heading home. Nothing terribly dramatic about any of it on the surface but “it’s such fun.” It’s a lovely reminder of the luminous beauty of everyday experiences, with a little extra touch of Biblical wisdom (“You’re going to reap just what you sow”) added for good measure.

7. “Berlin”

When making a list like this, you just can’t not add something from Berlin. This is the romantic prologue to one of Reed’s bleakest records, which, given his discography, is saying something. While he hadn’t actually been to Berlin before writing and recording the record, Reed was compelled by the idea of a divided, war-torn city and he used it as an ambient backdrop for some of his most gut-wrenching material. A drug dealer and a woman in distress emotionally slug it out over a series of songs—while the premise is anything but romantic, there’s something poetic amid all the darkness. The title track is all hushed but evocative minimalism, delivered in a breathless whisper as if a harsh word would shatter the illusion of peace: “In Berlin/ By the wall/ You were five feet ten inches tall/ We were in/ A small café/ You could hear the guitars play/ It was very nice/ Candlelight and Dubonnet on ice/ It was very nice/ Oh honey it was paradise.”

8. “Street Hassle”

One of the overlooked masterpieces of Reed’s solo career, this song is maybe better understood as a trilogy of three different songs in one. It begins with a random hookup—“Ooh baby, you know that I’m on fire and you know that I admire your body, why don’t we slip away?”—that turns into something else entirely: “he made love to her gently/ It was like she’d never, ever come.” The surging cello lines underline the poignance of this tough-minded narrative as fleeting bliss turns morbid. The story unfolds via overheard dialogue: another person’s sketchy response to the woman’s fate throwing some gritty shade on the surprise romance. And none other than Bruce Springsteen appears in the midst of the story as a kind of Greek chorus, reciting some lines that play off of the title of one of his best-known songs. Reed once said that his ambition for this song was “to write a song that had a great monologue set to rock. Something that could have been written by William Burroughs, Hubert Selby, John Rechy, Tennessee Williams, Nelson Algren, maybe a little Raymond Chandler.” By the end of the song, you might think that he just might have pulled it off.

9. “Busload of Faith”

Anything from 1989’s New York could make this list—there’s a reason why it’s considered one of Reed’s greatest solo efforts. As a concept album, it was intended to be listened to in one sitting, the way a novella or a movie might be consumed—all the better to give Reed’s jaundiced tales of Gotham’s high and low life their due. This song offers an almost journalistic immersion into life on the mean streets, which at the time were still ravaged with urban decay: “You can depend on the worst always happening/ You need a busload of faith to get by.”

10. “The Trouble with Classicists”

Not many singer/songwriters could boast of having been close with one of the most influential artists of the 20th century. Andy Warhol was a patron for the Velvets and encouraged the young Reed to “leave all the dirty words in.” Years after their acrimonious split, Reed and Cale reunited to record Songs for Drella their tribute to the pioneer of pop art. Drella was their nickname for Warhol, combining Cinderella and Dracula. Snippets from Warhol’s notebooks and journals inspired the lyrics, including an excerpt from Warhol’s papers, which is recited by Cale and becomes something like a posthumous monologue. This song offers a look into Warhol’s—and by extension, Reed’s and Cale’s—contentious relationship to the mainstream: “The trouble with a classicist he looks at a tree/ That’s all he sees, he paints a tree…I like the druggy downtown kids who spray paint walls and trains/ I like their lack of training, their primitive technique/ I think sometimes it hurts you when you stay too long in school.”

11. “Magic and Loss”

After two of Reed’s close friends—the legendary songwriter Doc Pomus (who gave Reed his start as a songwriter-for-hire) and a not-so-legendary person known as “Rita,” who was most likely Rotten Rita, a former member of the Warhol crowd—suddenly died, Reed responded with this album-length song cycle. How perfectly Reed-like to be equally wounded by the loss of an American musical legend and a marginal figure in the New York art underworld. The songs consist of mournful and hauntingly simple explorations of death and the survivor’s emotional aftermath. The whole record is a moving and somber meditation on life’s transience, finished with some hard-won wisdom that comes out of the other side of heartbreak. The concluding track from Reed’s arguably most vulnerable period sums it all up as well as any song can: “There’s a little magic in everything/ And some loss to even things out.”

12. “Set the Twilight Reeling”

In the mid ’90s, Reed was something of an elder statesman of rock. He’d been in the game for decades, inspired countless important bands, gotten extremely high in the ’70s and yet by this point had managed to maintain a lengthy sobriety. He was newly in love with Laurie Anderson, who was to be his companion up until the very end of his life. The title track from this mature record talks frankly about how age hasn’t softened or flummoxed him and instead how he has grown to “accept the new man/ and set the twilight reeling.” The live clip here is especially life-affirming in its intensity.

13. “The Raven”

It takes some serious guts to rethink the works of Edgar Allan Poe, especially his most famous poem of all. And it’s kind of awesome that a remake of the poem should include a phrase like “arrogant dickless liar.” As Reed explained in an interview with Greil Marcus, the goal wasn’t necessarily to rewrite Poe but to be inspired by his writing and see what kind of songs could be written and performed using his morbid obsessions as a starting point. The record is often overlooked in Reed’s discography, contains some airballs, and takes a little getting used to but contains some powerful moments. Famous friends like David Bowie, Ornette Coleman, and Willem Dafoe also add their distinct voices into the mix of Poe’s obsessive topics: guilt, paranoia, and the voluptuousness of doom.

Image credit: Unsplash/Andrey Konstantinov.