These vagabond shoes,
They are longing to stray
Right through the very heart of it:
New York, New York.
—"New York, New York," Frank Sinatra
For a long time, my only context for the song "New York, New York" was a
Get Fuzzy comic strip. In the strip, the beleaguered human Rob, the cruel and self-centered cat Bucky, and the nice but clueless dog Satchel are riding in the car, when "Somewhere, Over the Rainbow" comes on over the radio. Satchel
tries to sing along, but he gets the song wrong and blurts "I wanna be a part of it, New York! New York! Wait...is that right? That's not right." Bucky calls him a nerd, Rob tells Bucky to be nice, and
—scene: a classic three-panel comic strip.
I read this strip in high school, and without knowing what "New York, New York" actually sounded like, I was free to imagine it as I would. My mind created a sort of classic rock song with an uptempo guitar riff and a lead singer belting out "I wanna be a part of it!" with some back-up singers quickly chirping "New York! New York!" behind him. Needless to say, this is nothing like the original downbeat, groovy big-band lounge act that Frank Sinatra actually put on when he famously sang the song, and my mind was slightly blown when I heard it for the first time and discovered how wrong I was.
New York itself was the same for me. The city is depicted frequently in movies, TV, and other media that I frequently consumed as a child, so growing up I had a vague idea of what it was probably like: tall shiny buildings and bustling streets full of taxis and wise guys and cops and movie stars. Seeing it in person was radically different. Here's how it happened.
In college, my friend Daniel planned a trip to New York. I'm unsure what originally gave him the idea to do this; perhaps it was simply the new freedom of semi-adulthood combined with the realization that he'd never explored the nation's most well-known metropolis. At all events, he planned the trip and invited some relatively new friends of his: myself and our mutual acquaintance, Maxwell, as well as someone neither Maxwell or I knew, a fellow undergrad I'll call Allen. More about Allen in a moment.
The cool thing about this trip for me was that it was put together by someone else. I have never excelled at figuring out what I want in life, and trips to faraway places are no exception. Before going to New York, my biggest trip had been a family vacation to Mexico City and Puerto Vallarta. If my folks had come to me for advice, we all would have spent it inside with the blessed air conditioning and a good book. Thankfully, just as on our trip to Mexico my family and friends planned excursions to pyramids and restaurants and markets, on the New York trip, Daniel had put together an itinerary that included visits to
The Museum of the Moving Image,
Strand Book Store,
MoMA, and a variety of other places I'd never heard of, as well as a plan to hit Broadway and meet a friend who lived in the city.

We got to New York, and I found that the key difference between my mental image of the city and the real thing is the utter, utter vastness of the real thing. I live in Chicago and work downtown; Chicago is the City that Works, and its downtown is busy, large, and full of people and big buildings. New York, though, is larger than Chicago in terms of both population and size by what must be at least an order of magnitude, right? It's excessive. If you head to the busier parts of the Loop in Chicago during rush hour, you can get a little uncomfortable walking because of the crowds; you might, say, brush past someone or even bump into them if you're not careful. In New York, there are parts of downtown where there are so many people on the sidewalk that breathing, not bumping, is the issue of concern. Put it another way: just compare the CTA rail map and the MTA rail map. The former is extensive but comprehensible; the latter is mind-shatteringly huge and complex:

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