I ? NY: Chicago-versus-New York comparisons are lame, but I can't help myself
PLUS: I Hate New York video
Jeff Ruby hated the sleazy, scary New York of the past—but he hates the sterile, safe New York of today even more. Here, his angry rant against both Manhattans
In my first trip to Manhattan, a pigeon dropped a load on my dad’s shoulder, then flew off into Battery Park. It didn’t take an English major to see the symbolism there, especially for a dyed-in-the-wool Midwesterner like me, who hated New York before I could even spell it.
While traveling abroad during college, I once challenged an East Coast snob to draw a map of the United States, and he came up with an amorphous blob with nothing between Ohio and Nevada. (It looked eerily similar to that famous cover of The New Yorker that depicted Manhattan in great detail and everything west of Jersey crammed into a mostly barren rectangle. But my guy wasn’t trying to be funny.) When I mentioned that he’d forgotten a few states, he thought for a moment and then added Minnesota and Texas, their borders kissing somewhere near where Missouri should have been. I felt like my dad’s shoulder. With a single sketch, the kid had wiped 100 million Americans from existence—and fossilized my geographic prejudices for decades to come.
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As an angry young journalist years later, I pitched a Chicago–versus–New York feature for this publication: In impossibly clever ways, I would compare every important aspect of both cities, and after careful analysis (they suck; we rule) I would declare Chicago victorious. The boss gently said no. He explained that the Chicago-NYC face-off was one of the stalest themes in local journalism, this rah-rah stuff was amateurish, and any comparison could only devolve into dogmatic floundering about bagels and skyscrapers. I did not pitch another story for three years.
Fast forward to Oscar night, 2003: Chicago is up for Best Picture against Gangs of New York. When Rob Marshall’s sumptuous musical wins, I’m surprised to find myself thrilled, subconsciously identifying this as a victory for my city. The fact that it was filmed in Toronto was a mere asterisk on our triumph over the forces of evil. Up yours, Scorsese!
In the years that followed, when Chicago started winning everything else—the World Series, Top Chef, the presidency—the city around me began to affect a distinct swagger. I did not share its confidence. While everyone else in town was acting all cool, as though we’d had dozens of intellectual Hyde Parkers in the White House over the years, Chicago’s triumphs only peeled a scab off my neuroses. Somewhere in the afterglow of Obama’s election, I went on Whitehouse.gov to find out when the last New Yorker was president (In your face, FDR?), then erased my laptop’s search history to hide my lingering feelings of inadequacy.
In post-Obama Chicago, though, I’m no longer allowed to hate New York. As a writer, a liberal, and a freethinking human, I am required to gaze lovingly toward Manhattan. And the New York–Chicago rivalry, at least outside of pizza message boards, is no longer acknowledged by anyone in either city. We’re all supposed to accept that these two complex cities—maddening and mesmerizing in their own special ways—are apples and onions. Are they equal? To ask the question is to mark yourself as a provincial twit, but I can’t just stop cold turkey.
On a recent trip to New York, I did my best to avoid making the inevitable urban comparisons, instead seeking out positives. My compliments tended to be halfhearted (“their street performers are pretty good” . . . “their stoplights are certainly well timed”), but baby steps were all I was capable of. For one lovely moment while crossing the Brooklyn Bridge, I surrendered to the city’s infectious vibe, and my rage faded into nothing more than the nagging suspicion that loathing an entire city based on little more than a pigeon and a map was just silly.
Philadelphia, though? The worst.
VIDEO BY JEFF RUBY; Illustration by Monika Melnychuk/www.i2iart.com


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Reader Comments:
Awesome pictures - well done!
So true - New York used to be filthy and interesting. Now it's just filthy and the home of Trump.
And their pizza sucks as well.
Lord, Chicago and its unwavering inferiority. Oprah and deep-dish pizza do not a great city make. And NYC's pizza is way better, anyways.
Is it me, or does the tagline of the video have NOTHING to do with the actual story?
To write this article is to lose the argument.
Im pretty sure you could ask people anywhere in the US to draw a map of the entire US and not just the NY'ers would massivly fail. I think NYC is hard to love when you're just visiting. I didn't start loving NYC until I lived here. I never realized there was such a Chicago/NYC competition and think it's a little weird that you'd focus so much energy towards it. I've always thought Chicago seems like a pretty cool place...
This reminds me of a story Chicago mag ran years ago by a woman who wrote for the ill-fated Joan Cusack TV show. In one anecdote, she told how members of the crew were astounded that Chicago actually had -- gasp! -- sushi.
So I think Chicagoans have a problem with New York because New Yorkers tend to overlook Chicago (and everywhere else that's not LA). Or at least we think they do, which might be the bigger problem.
Having grown up in the midwest, visiting Chicago many many times, and now living in New York for the past 15 years, I find it odd the two are compared so much. It bothers me to no end when people say "Chicago is a smaller New York." No, it's not. Chicago is so midwest, it's a bigger {insert any midwest metropolis here} and has nothing to do with New York. which isn't a bad thing. I love both cities, but what's to compare? Seriously.
Of course it's ok to sit there and write about your neurotic Chicago vs New York comparisons to inflate your obviously low sense of geographical self as long as you dump on Philly in the end, which killed your piece and made you look like a snotty douchebag. Fail.
I grew up in NYC and NJ and have recently moved to Chicagoland and I have to say that I had never even heard of this supposed rivalry until I moved to Chicago. What's with the inferiority complex, Chicagoans? New Yorkers never even bothered (except when it comes to some seriously intense pizza arguments).
Chicago has better food. New York has better looking girls. Take your pick I guess.
I was born and raised on the northside of Chicago. The first time I went to New York back in 1986 at the age of thirty - I loved it. I loved everything about it. Okay so maybe I "romanticzed it way out of proportion." Then I went again two years later - and loved it all over again.
But I'm not a Chicagoan that wishes I was in New York. I love Chicago, it's the greatest city in the world. One afternoon I made my usual stop at the Starbucks on Rush street and over heard a woman (I think she was in apparell) say she was moving to New York. "Why stay in Chicago when everybody here wants to be in New York, anyway." Whaaaaat? Really? So every Chicagoan secretly wishes they lived in New York City? Oh, okay.
I mean I loved New York but never once thought I'd want to trade it in for an apartment on the Upper West side. Never in my life.
First of all, this supposed rivalry only exists in the minds of Chicagoans. People in New York would never even think about this because Chicago is nowhere near the caliber of New York, in terms of being an alpha world metropolis. It would be like a high schooler entertaining a rivalry with a middle schooler.
So Chicago's pizza crust is five times thicker, so it finally claims a president and some recent sports championships, like many other major cities and states. Chicago is not even a world capital of anything (except maybe higher education, but so is New York). New York is a world capital of like a dozen major industries, and also claims fabulous multi-cultural cuisine and countless luminaries. The only rivalries that New Yorkers regularly entertain are the ones between Los Angeles (sunny laid back Hollywood vibe vs. cultured intellectual subways and skyscrapers) and London, which competes with New York as the world financial capital. And the only U.S. city remotely similar to New York is San Francisco.
But New Yorkers long ago accepted these illusions of "rivalry." Because whenever we tell people where we are from, whether they are from some Minnesotan suburb or Kentucky farm or California beach, there are always some who feel compelled to argue why New York is such an awful place to live compared to where they're from. Personally, I find it rude because I would never bash their suburban or country lifestyle to their face, especially during introductory conversation.
Fact is, it's a matter of preference. Chicago is a perfectly great place to live. But if you're talking "rivalry," it ranks behind New York in everything lasting and consequential.
And another thing, I don't get why Ruby is talking about all these things he "misses" about New York in his rudimentary poem/ photo montage when he says in the column that he has hated the city until now (that Chicago has gotten some swaggering rights haha). And then he contradicts his last line of the article - "and my rage faded into nothing more than the nagging suspicion that loathing an entire city based on little more than a pigeon and a map was just silly" - by saying "I hate New York" over and over and over again. Clearly the last moments of his trip were nothing like what he wrote in the last paragraph. Totally ridiculous.
Everyone knows that Chicago is best seen from thirty thousand feet with a cocktail in your hand...
your inferiority complex is showing like a ripped polyester slip. but if reinforcing tired stereotypes is your thing, new york kindly asks that you kiss theirs.
your inferiority complex is showing like a ripped polyester slip. but if reinforcing tired stereotypes is your thing, new york kindly asks that you kiss theirs.
Has Jeff Ruby ever been to Philadelphia? It's a beautiful city, outstanding museums, a vibrant night life, plenty of good and inexpensive housing. Yes, we have a reputation for booing Santa Claus and being hard on our professional athletes but you never, ever have to worry whether someone is being nice just for the sake of decorum. Philadelphians are direct. And in the course of being direct, Jeff Ruby, you're a moron.
I think the fact that this rivalry exists only in the minds of Chicagoans is a big give away.