There’s a reason this swanky tune about a small-town striver with big-city dreams never goes out of fashion. It’s NYC to a T—a champagne-fizzy success fantasy that only a Jersey native like Frank can truly understand. “It’s up to you,” Sinatra croons, like he’s catching his reflection in a storefront window en route to a meeting that could change his life.
Peak Position: No. 32, Billboard Hot 100
Peak Date: June 14, 1980
"Fairytale of New York," The Pogues Featuring Kristy MacColl
The only Christmas song to feature the words “scumbag” and “maggot” (and worse), this classic duet between Pogues leader Shane MacGowan and U.K. singer Kirsty MacColl turns from fairytale to nightmare as two lovers get soused and air their grievances on the streets of NYC. The final verse ends with hope—“I’ve built my dreams around you”—but Shane’s telling the tale from the NYPD’s “drunk tank,” so it could go either way.
Peak Position: No. 22, Holiday Digital Tracks
Peak Date: Oct 29, 2011
"Empire State of Mind," Jay Z + Alicia Keys
Having gone from slinging crack in Brooklyn’s Marcy projects to hobnobbing with DeNiro in Tribeca, Jay takes a much-deserved victory lap. As he rolls past his former “stash spot” en route to the Garden, where he’s got courtside seats, Hova celebrates the city as much as he does himself. “These streets will make you feel brand new,” sings fellow hometown hero Alicia Keys, delivering a message too true to sound corny. “Big lights will inspire you.”
Peak Position: No. 1 (five weeks), Billboard Hot 100
Peak Date: Nov. 28, 2009
"N.Y. State of Mind," Nas
In this harrowing ‘90s hip-hop classic—which couldn’t be more different than Billy Joel’s similarly titled light-pop favorite—rapper Nas details criminal drug culture in parts of the city that tourists never see. “I never sleep,” Nas raps, putting a chilling spin on NYC’s catchphrase, “‘cause sleep is the cousin of death.”
"New York, New York," Ryan Adams
In this Dylanesque roots-rock jam, Adams jumbles images of a girl he loved and the city where he loved her. He’s got memories spanning the Upper West Side to Alphabet City, and while things ultimately went sour, he still thinks sweetly about his freewheeling days in Manhattan: “I’ll always love you New York.”
Peak Position: No. 1 (three weeks), Adult Alternative Songs
Peak Date: Dec. 1, 2001
"New York New York," Grandmaster Flash & the Furious Five
Forget those double-decker bus tours through Times Square. On this ’83 slice of realist hip-hop, Melle Mel and the gang reveal what actually goes down in this “big city of dreams.” There’s greed, poverty, hunger, crime, mental illness, and police brutality -- and yet the funkiness of the track adds a certain allure. The city will kill you, but where else can you feel so alive?
Peak Position: No. 17, Hot R&B/Hip-Hop Songs
Peak Date: June 25, 1983
"53rd & 3rd," The Ramones
Anyone who longs for the gritty New York of the ‘70s ought to listen to this punk classic, all about a drug-addicted Vietnam vet selling his body on the titular street corner. “Don’t it make you feel sick?” asks frontman Joey Ramone in the chorus. By the time bandmate Dee Dee shows up in the third verse with his switchblade, the queasiness has definitely set in.
"Welcome to New York," Taylor Swift
Fresh from a real-life move to Manhattan, Swizzy loses herself in the city’s romantic promise. “Everybody here wanted something more,” she sings, giddy as the synths and snappy beat signaling her transformation from country star to pop goddess. “Searching for a sound we’ve never heard before.” The bohemian spirit is alive and well in Taylor’s $15 million condo.
Peak Position: No. 48, Billboard Hot 100
Peak Date: Nov. 8, 2014
"No Sleep Till Brooklyn," Beastie Boys
Props to the Beasties for lampooning heavy metal while big-upping Brooklyn, birthplace of Adam “MCA” Yauch (RIP). Less of a novelty than “(You Gotta) Fight for Your Right (to Party!)”—their similar-sounding breakthrough hit from the same year -- this 1986 rap-rock staple remains a source of pride for BK residents. The message: The world is your hotel room -- trash it while you can.
Peak Position: No. 18, Alternative Digital Songs
Peak date May 19, 2012
"Brooklyn," Jesse Malin
You know it’s a bad breakup when she doesn’t just move out—she moves to another borough. On this downcast, noise-spiked acoustic ballad, punk-rock troubadour and NYC native Jesse Malin pines for the girl who broke his heart and relocated to Brooklyn. “No more couches to surf,” he sings, closing the book on a chapter in his life. “Only beaches in your dreams.”
"Deja Vu (Uptown, Baby)," Lord Tariq and Peter Gunz
With this 1998 shout-out to the Bronx, young bucks everywhere got a valuable history lesson. “If it wasn’t for the Bronx, this rap s— probably never would be going on,” raps Lord Tariq, repping for the borough that birthed hip-hop culture in the ‘70s. The song also provided a lesson in copyright law—the uncleared sample of Steely Dan’s “Black Cow” cost Tariq and Gunz millions.
Peak Position: No. 9, Billboard Hot 100
Peak date March 28, 1998
"Yeah! New York," Yeah Yeah Yeahs
Over piercing, slicing guitars, Karen O throws a one-woman punk-rock pep rally for the city and herself. “Yeah, New York!” she shouts, expressing her enthusiasm with an economy of words. “Yeah, Big Apple—let’s go!” Her hair is red, her eyes are pink, and she’s ready to rock.
With its parade of phonies and wannabes, New York can be kind of a drag. On this creeping post-punk slow-burn, Interpol singer Paul Banks realizes he needs to “turn on the bright lights” in his dark cellar of a soul. “The subway is a porno,” sings the jaded rocker, finding poetry in his misery. “The pavement is a mess.”
"New York Groove," Ace Frehley
On his killer 1978 cover of a tune first recorded by UK glam band Hello, Kiss guitarist (and Bronx native) Ace Frehley locks into the rhythm of the streets. It’s a cocksure cross between a stomp and a strut, and it’s a beat that won’t quit. “I feel so good tonight,” Ace sings, surveying the scene from the back of his Caddy. “Who cares about tomorrow?”
Peak Position: No. 13, Billboard Hot 100
Peak date Feb. 3, 1979
"New York, I Love You But You're Bringing Me Down," LCD Soundsystem
On the weary finale of LCD’s great Sound of Silver album, frontman James Murphy describes NYC like an old man might his spouse. “There’s a ton of twist,” he sings, grumpy-Kermit style, over atypically melancholy piano chords. “But we ain’t got much shout.” It’s the classic New York conundrum: The city ain’t what used to be, but it’s still better than everywhere else.