Rap Songs to Soundtrack Your Walk Through New York City

Walk with this... Late at night in an unknown neighborhood.

While current day New York is far from the gritty city that sparked movies like Taxi Driver and groups like Wu-Tang Clan, there are still pockets that remind you: New York can be a dark, dangerous city. Like any America metropolis, you have to keep your guard up for certain stretches. Mobb Deep's seminal "Shook Ones Pt. II" is the anthem of life on the edge, the sound of young men in a persistent state of paranoia, defenses forever up. From its skeletal, dust-caked production to Prodigy and Havoc's coldly violent performances, "Shook Ones Pt. II" is the sound of agitation in parts unknown, a dish best served on dark nights with a chaser of pressure-cooked desperation.

Walk with this... If your blunts are laced and you're walking around at sun up after a particularly harrowing night.

Like Mobb Deep's quirky, comic book-obsessed cousins, Cannibal Ox emcees Vast Aire and Vordul blended the ever-on-edge mentality of 9/11-era New York with a sci-fi bent that, melded with El-P's cinematic production, created one of independent hip-hop's most cherished albums, The Cold Vein. Lead single "Iron Galaxy" crystallized their outlook, a portrait of Harlem life cast through a decidedly abstract, kaleidoscopic lens–descriptive, threatening, mournful, and unexpectedly ecstatic. Another end of the Harlem spectrum for those who know the neighborhood primarily through A$AP Mob, Dip Set, or Big L.

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Walk with this... On your way to the subway, alone at four in the morning.

In New York, there are two types of paranoia, roughly speaking. There's the Mobb Deep "I can die any die because I invite death" paranoia, and the more general "well, everyone is probably out to get me, so I can get it at any time" paranoia (the latter is familiar, at least in passing, to anyone who's ever ridden a train or bus in New York). While Roc Marciano raps about the perils of hustling in New York City, that second sense of pervasive, constant heightened awareness hangs over his music. "Panic" perfectly encapsulates that sound, it's droning bass, off-kilter percussion, and sharp snares doing their very best to mirror the song's title down to the letter.

Walk with this... Right before the night turns to dawn in Times Square or the deserted area of your choice (bonus points for one of the boroughs connected by the bridge formerly known as the Triboro Bridge).

Abandoned streets: one of New York's strangest sights. In a city so packed to the brim with life and activity, it's even surprising for a native to find blocks and occasionally whole avenues deserted, eerily quiet (the sound of nearby traffic becomes white noise). Even Times Square, one of the city's most densely populated and chaotic areas during the day, evaporates into eerie, brightly-lit vacancy in the wee hours of the night. Big Pun's "Tres Leches (Triboro Trilogy)" (fittingly featuring the sultan of thug paranoia, Prodigy, and Inspectah Deck) is the sound of deserted New York streets through and through, its icy RZA production evoking the silent alertness–a paradoxical state of calm agitation–that accompanies most solo late night walks in New York.

Walk with this... Along 125th street in Manhattan, checking out classic New York sites like the Apollo near new developments like modern soul-food restaurant Red Rooster.

Popular rap coming out of New York has changed drastically over the past decade, shifting to represent a far more national (and largely southern-influenced) sound. A$AP Rocky exists as the most prominent product of this new wave, riding southern product and midwest flows to chart-topping success. His A$AP Mob cohort A$AP Ferg plays the livewire to Rocky's smoother "pretty mothafucka" persona. New single "Shabba" is a humorous display of both rappers' personalities and a clear example of the influence that has crept into New York hip-hop from across the United States.

Walk with this... Drinking some ungodly punch mixture in a red solo cup and walking through Alphabet City on the way to a bar.

When my parents were growing up in New York, neighborhoods like the Lower East Side, East Village, Chinatown, and their surroundings were purely the domains of junkies, artists, junky artists, and violent delinquents. You didn't go to Alphabet City; you barely had a reason to be below 14th street (unless you were going to the now defunct Fulton Fish Market). Now, Manhattan's eastern downtown bits are a hot bed of creativity, nightlife, culinary surprises, and more music than anyone really knows what to do with. Even though they're Brooklyn-based, Weekend Money fits right in with this vibe: A little dirty, party-loving, and inventive. Producer Baghdaddy's skeletal percussion and bass on "Hol' Up" could start a party while Ne$$'s rapping puts on a clinic in stylish syllable stacking.

Walk with this... On a nice summer day (bonus points if you're in the Bronx) on your way to a BBQ.

The term "one hit wonder" is often used derogatorily, but sometimes one hit is all you need or want from an artist. Lord Tariq and Peter Gunz's "Deja Vu (Uptown Baby)" is an irresistably sunny ode to the Bronx–so irresistible that it was able to ascend from bouncy regional anthem to #9 on the Billboard Singles chart–that's as much fun today as it was when it hit the airwaves in 1998. Tariq and Gunz shoutout all boroughs, but pay special attention to their BX home. No matter what part of New York you're in, "Deja Vu" is the sound of summery possibility (despite being released in February), it's schools letting out in June, just as it gets nice and hot–but not oppressively hot, not end of Do The Right Thing hot.

Walk with this... As spring kicks into gear in Astoria.

If girls are your thing, there's no better time to be in New York than than the peak of spring. As the city thaws, the clothes start coming off–the outfits become skimpier, and often outlandishly so. If you're a teenager being assaulted by hormones, New York in the spring time can be a place of awakening, excitement, and confusion. "Bonita Applebum" plays the perfect ode to lust disguised as first love, discovery, and chase. Q-Tip's lackadaisical delivery and the classic chorus chant–"Bonita Applebum/You gotta put me on"–embody young flirtation perfectly: Trying to seem removed, but wanting to win the would-be prize so badly.

Walk with this... To the corner bodega to pick up another six pack.

When spring turns to summer, the heat mingles with unbearable humidity (which anyone from the south laughs off) and makes New Yorkers into whiny, irritable brats in search of air conditioning like rats to leftovers. Relax. Grab a fan and an ice cold beverage, take off a few layers, and throw on Action Bronson's "Shiraz," the smooth track that provided an introduction for many to the now fan-favorite emcee's world of drugs, food, liquor, women, and exotic locales. If you're the active type, Bronson's lyrics might make your mind race with summer schemes. That flute sample? That's telling you to chill for a second.

Walk with this... To wherever you plan to perch and watch people. Take a break, you've been walking for a while.

Some of the world's finest people-watching unsurprisingly happens in a city that plays host to diverse cast of over eight million people. A long walk will expose you to a variety of neighborhoods and characters, but sometimes the best strategy is to post up on a corner, at a restaurant, or in a place like Grand Central Station and watch the unpredictable parade of humanity roll by. Aesop Rock's testament to the New York's many faces, styles, and ideas, "6B Panorama" sharply catalogs the juxtapositions that give New York its representation as a northern gumbo full of surprises.

Walk with this... Holding a six pack of Coronas (or your summery beer of choice) on the way to a BBQ.

Who says "conscious" rap can't be fun? On the KRS-One sampling lead single from Black Star's self-titled debut album, the duo of Mos Def and Talib Kweli toss bars back and forth over a sunny, reggae-tinged beat, never concerning themselves with some of the weightier matters they deal with elsewhere on the LP. "Definition" is playful and lively, relaying the kinetic energy that surrounded New York's underground scene at the turn of the century.

Walk with this... Through Spanish Harlem or down Avenue C.

If you've spent a day walking arond New York, you've almost certainly heard someone (or a lot of someones) speaking Spansh. It's the city's unofficial second language, so common that our outgoing Mayor Bloomberg infamously delivers his public service announcements twice over: Once in english and once in Spanish, so stilted that it spawned an excellent Twitter parody account. If you're trying to pick up a date while you stroll through the city, it certainly wouldn't hurt your chances to know a bit of Spanish. Unless you're learning it from The Beatnuts' "Se Acabo," which opens with a line that translates to "shut your mouth and take off your panties." Even if you don't speak Spanish or intend to learn, The Beatnuts' production serves up a perfect soundtrack to summer mischief.

Walk with this... Down Broadway, feeling like the King or Queen of New York.

If you're young and living in New York (or, hell, if you're almost any age and living in New York and you're not a banker or working for Google), you probably have less money than you'd like. With no shortage of budgetary obstacles and an abundance of creative minds, New Yorkers figure out ways to dress, walk, and generally exist with a certain measure of swagger. Ghostface Killah's utterly triumphant Supreme Clientele single "Apollo Kids" is the sound of invincible swag, from its bombastic Solomon Burke-sampling production to Ghostface's densely referential semi-narrative, from copping a pair of discounted kicks ("A pair of bright phat yellow Air Max/Hit the racks, snatch 'em up, son, twenty dollars off no tax"), to not letting a little rain water and mockery stop Ghostface's shine ("Heavy rain fucked my kicks up/Wasn't looking, splashed in the puddle/Bitch laughing, first thought was beat the bitch up/Moseyed off gracefully, New York's most wanted cheeba hawk").

Walk with this... Anywhere in the city. You'll feel like a giant.

Completing this mini-Mount Rushmore of swagger, "All About The Benjamins" stomps with undeniable force and style all its own, as fitting in the speakers of a pack club as in a jeep, busted boombox, or iPod. Puff Daddy and the Family (you didn't really think we'd get through this list without at least one Notorious B.I.G. appearance, did you?) show utter disdain for having anything but big bills and all the accompanying spoils on "Benjamins," and conspicuous consumption never sounded better. Even if you only have lint in your pockets, "All About The Benjamins" will make you feel like you've got enough dough to make it rain at any club you please.

Walk with this... Right past Red Rooster to Sylvia's for some unadulterated, classic soul food.

If you prefer your Harlem hip-hop a bit more classically-leaning, the Diplomats' soul-sampling anthem "I'm Ready" is a perfect blend of aspirational New York attitude and vibrant production. Coming at the beginning of Cam'ron and company's reign over a cultish New York fanbase, "I'm Ready" is the sound of one star (Cam'ron) and his two soon-to-be-star-sidekicks (Juelz Santana and Jim Jones) as they arrive near the top of the mountain, victorious music that never forgets the depths of the struggle that inspired it. "I'm Ready" is the New York hustler story in a nutshell, a reminder of the gutsy, stylish characters Harlem is famous for.

Walk with this... While you protest a good cause in Union Square

When a verdict was delivered in the recent George Zimmerman trial, outraged New Yorkers organized peaceful, large-scale protests in Union Square and Times Square, two of the city's most famous gathering places (The former: a hotbed of performance art, skateboarders, rallyers, protesters, and colorful drunks. The latter: probably much the same, except you can't tell because there are too many damn people there). This measured response to injustice served as a reminder (as the Occupy movement did at its peak) that New York is a city teeming with people waiting for the right reason to get out of their homes and get mad as hell. The humanist paranoia–founded squarely in race, the central concern rearing its only-ever thinly veiled head once again in the national dialogue–central to Public Enemy's "Welcome to the Terrordome" is this undercurrent of righteous anger personified in sound.

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