100 best NYC songs: Nos. 30–21

Watch music videos for iconic NYC songs by Lou Reed, Suzanne Vega, Stevie Wonder and more.

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30. Bobby Womack, "Across 110th Street" (1972)

The genius of this funk-soul marvel lies in the way it captures the Greek-tragedy-caliber pathos of ghetto life, portraying both the pimps and junkies and the up-and-comers desperately seeking a way out. Penned for a blaxploitation film of the same name, the song portrays Harlem as the ultimate crucible: "You don't know what you'll do until you're put under pressure," croons Womack, who grew up in Cleveland and clearly knows a thing or two about urban poverty. "Across 110th Street is a hell of a tester."—Hank Shteamer

Across 110th Street - The Best of Bobby Womack - The Soul Years

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29. Jennifer Lopez, "Jenny from the Block" (2002)

In this 2002 chart-topper, J. Lo insists that even though she's now a superstar, she hasn't forgotten her Bronx roots. This was close to the beginning of her stardom; since then she's racked up sales of more than 55 million albums, plus awards for acting ventures. "Used to have a little, now I have a lot," she insists. Whether she's still Jenny from the block is questionable; the track's catchiness is not.—Marley Lynch

Jenny from the Block (Track Masters Remix featuring Styles & Jadakiss) - This Is Me...Then

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28. Suzanne Vega, "Tom's Diner" (1987)

The original version of Suzanne Vega's stark, unaccompanied melody sounded like antifolk before there was antifolk; by contrast, the big-hitting version that blared out of cars and Walkman earphones for most of 1990 was remixed by DNA, refurbished with a Soul II Soul beat. Yet the essence of its story held fast—a girl sits in a diner, reads the paper, watches customers and drifts occasionally ("I am...thinking of your voice"). Just as the song is specific but endlessly remixable (as 1991's Tom's Album attested), so too Tom's Restaurant, a real eatery in Morningside Heights, could be anywhere.—Sophie Harris

Tom's Diner - Retrospective: The Best of Suzanne Vega

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27. Simon & Garfunkel, "The Only Living Boy in New York" (1970)

After Art Garfunkel ditched a planned songwriting session for a trip to Mexico, Paul Simon penned this veiled sonic fuck-you to his partner. In it, he sings of a special kind of loneliness known to New Yorkers, who often wonder why it doesn't seem like there's anything to do in the city where the options are limitless. But the key lyric is the song title itself, which speaks to the idea of being the only one who's truly alive in a city of 8 million anonymous souls.—Sharon Steel

The Only Living Boy In New York - Bridge Over Troubled Water

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26. Elton John, "Mona Lisas and Mad Hatters" (1972)

"Now I know that rose trees never grow in New York City," sings John in the first verse of this disillusioned song from his Honky Chteau album. (Bernie Taupin's lyric riffs on a line from Ben E. King's "Spanish Harlem.") But despite his anger at the Big Apple's benighted upper classes—inscrutable and crazy as the figures in the title—he soldiers on with the faith that if he goes his own way, "[his] own seeds shall be sown.—Adam Feldman

Mona Lisas and Mad Hatters - Honky Chteau

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25. Stevie Wonder, "Living for the City" (1973)

Yes, Stevie Wonder hailed from Detroit; yes, the protagonist of this urgent Innervisions track is from small-town Mississippi. But listen past the first fade to the dramatic interlude at the track's heart, and you'll hear the tale of a wide-eyed new arrival in NYC stung immediately as a drug mule and tossed in the can for a decade. The anger in Wonder's voice is genuine, fueled by social injustice and by his collaborators, who forced take after take of the song just to piss him off for effect.—Steve Smith

Living for the City - Stevie Wonder: The Definitive Collection

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24. Ryan Adams, "My Blue Manhattan" (2004)

There's another Ryan Adams song further up our list (don't peek!), but we had to find a place for the prolific songwriter's two-and-a-half- minute confection "My Blue Manhattan" in the upper climes of our tally. Written long before Mandy Moore sweetened his perennially salty view on life, this piano-driven song about first snowfalls and boning the wrong people is clipped, classic Adams—and totally New York, which is exactly why we love it so much.—Sharon Steel

My Blue Manhattan - Love Is Hell

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23. Lou Reed, "Halloween Parade" (1989)

Ever on the lookout for another aspect of the NYC fringe to immortalize, Lou Reed hit pay dirt when he zoomed in on the West Village's annual queer-friendly costume bonanza. In his inimitable offhand style, he delivers both vivid reportage and a lament for a generation ravaged by AIDS. Reed never names the disease; instead, he catalogs the characters he misses ("There ain't no Hairy and no Virgin Mary/You won't hear those voices again") and gives himself a pep talk, exhibiting the resilience cultivated by every self-respecting New Yorker.—Hank Shteamer

Halloween Parade - New York

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22. New York Dolls, "Subway Train" (1973)

Country bluesmen couldn't get their minds off the railroad; in this Stonesy glam classic, David Johansen transposes that sentiment to seedy early-'70s NYC. He's lovesick, you see—smitten with a hooker who has to "get on back to Daddy"—and he finds solace in riding the subway incessantly and aimlessly, to the point that the conductor "thinks [he's] gone insane." Johnny Thunders's lead guitar blares like a train whistle, completing this quintessential ode to being bummed out in the Big Apple.—Hank Shteamer

Subway Train - New York Dolls

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21. Nas, "N.Y. State of Mind" (1994)

This sinister, piano-driven track introduced the world to the studied, Dickensian style of street reportage that would become Nas's trademark, all but transporting listeners to the street corners of his native Queensbridge, while offering one of the rap legend's most famed lines: "I never sleep 'cause sleep is the cousin of death."—Jesse Serwer

N.Y. State of Mind - Illmatic

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100–91 | 90–81 | 80–71 | 70–61 | 60–51 | 50–41 | 40–31 | 30–21 | 20–11 | 10–1


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