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100

In Nora Ephron’s 1989 masterpiece When Harry Met Sally, Harry and Sally meet on a road trip from college to New  York City. In what city did their road trip begin?

Chicago

100
  1. The 1975 studio album titled “Coney Island Baby” comes from which native New York musical act?

  2. Simon & Garfunkel

  3. Lou Reed

  4. The Velvet Underground

  5. The New York Dolls

Lou Reed

100
  1. “Ray’s Coffee Shop” from HBO’s Girls sat directly across the street from a hip, trendy cafe called “Helvetica.” Name the Brooklyn restaurant where “Ray’s” was set.

  2. Vinny’s Pizzeria

  3. Speedy Romeo

  4. Barboncino

  5. Paulie Gee’s

Speedy Romeo

100

In the first chapter of Mario Puzo’s The Godfather, the Corleones are celebrating a wedding. Which NYC borough is the wedding set in?

Staten Island

100

Brooklyn is named for the city of Breukelen in what European nation?

The Netherlands

200

In the 1991 film New Jack City starring Wesley Snipes, Judd Brown and Ice-T, Chris Rock (in one of his first film roles) plays a drug addict who goes by the name of:

  1. Cookie

  2. Pookie
  3. Snoopy

  4. Loops

Pookie

200

Dorothy Parker’s posse met for lunch every day for ten years at which Times Square hotel?

The Algonquin Hotel

200

In J.D. Salinger’s The Catcher in the Rye, Holden wonders about the fate of which animals in Central Park?
(a) The squirrels in the Sheep Meadow
(b) The goats in the Children’s Zoo
(c) The ducks in the lagoon
(d) The horses from the carriage tours

The ducks in the lagoon

200

The name of this, New York City’s most famous, mayor graces multiple locations across the city, including public housing facilities, schools, and even an airport.

(Fiorello) LaGuardia

300

Without his dancing skills, Tony Manero would just be a poor kid from Bay Bridge, Brooklyn in this 1977 classic:

  1. Juice

  2. West Side Story

  3. Saturday Night Fever

  4. Rosemary’s Baby

Saturday Night Fever

300

This New York jazz club was a famed venue for jazz legends Miles Davis, Billie Holiday, and John Coltrane.

The Lenox Lounge

300

This Greenwich Village cafe was a popular hangout for the likes of Jimi Hendrix, Bruce Springsteen and Bob Dylan in the 1960s and 1970s

Cafe Wha?

300
  1. In Truman Capote’s Breakfast at Tiffany’s, which character is hospitalized for a bad sunburn?

(a) Rusty Trawler
(b) Sally Tomato
(c) Holly Golightly
(d) Mag Wildwood

Mag Wildwood

300

The Bronx is home to this park, the largest in all of the City’s five boroughs.

Pelham Bay Park

400

It opens with a scene on the Staten Island Ferry and includes plenty of great New York views, but can you name this 1988 film which stars Melanie Griffith?

  1. Hannah and her Sisters

  2. Body Double

  3. Heartburn

  4. Working Girl

Working Girl

400

What NYC nightclub played a major role in the growth of disco in the 1970s?

Studio 54

400

What New York City neighborhood does Louise Fitzhugh’s nosy kid-detective Harriet the Spy live in?

(a) Upper East Side
(b) Greenwich Village
(c) Upper West Side
(d) Hell’s Kitchen

Upper East Side

400

This notoriously crime-ridden, lower Manhattan neighborhood was immortalized in Scorcese’s 2002 film, “Gangs of New York.”

"The Five points"

500

 In the early Seinfeld episode “The Airport,” Jerry picks up a woman he’s interested in from the airport. She gives him which unconventional greeting?

  1. Clasping both hands

  2. Hug from behind

  3. Secret handshake

  4. Salute

Clasping Both Hands

500

Name the home borough (or neighborhood) of these NYC rappers: Nas, Biggie, Fat Joe, A$AP Rocky, Cardi B

Queens (Queensbridge); Brooklyn (Bed-Stuy); Bronx; (Harlem); Bronx (Morris Heights)

500

Ralph Ellison's masterpiece, Invisible Man tells the story of a young college student in the 1930s who leaves the South for this bustling New York neighborhood.

What is Harlem

500

This astronomical occurrence, in which the rising or setting sun is perfectly aligned with the Manhattan street grid, is known by what name?

Manhattanhenge