What Does Chicago Say & Some Chicago Music

I've had a number of conversations in the past year about my new home - the city of Chicago - and the Midwest in general. Having already lived in Boston & Los Angeles, and spent a good deal of time abroad, I feel like I have experienced more cities than the average person and therefore feel qualified to discuss city living.

When I arrived in Chicago last August, I loved it. It's big and clean; you can find great houses and apartments at reasonable cost; it's relatively inexpensive & very "live-able;" people are friendly and generally peaceful (unlike, say, many Bostonians); there is unbelievable live music and great food; and it's full of solid bars with people drink like there's no tomorrow (this, I would contend, is a good thing when combined with the general peacefulness). Aside from the absolutely mind/body/soul-crushing weather for like 8 months of the year, it has everything you could ever want in a city. It's even easier to get to most places around the country from here than any other major city. A lot to like.

But Chicago lacks a certain "something" that neither I nor the few people with whom I had spoken about this could put our fingers on. Was it a Midwestern lack of "worldliness?" Maybe. The missing intellectualism of a Berkeley or Cambridge? Possibly, but it's hard to argue that with the University of Chicago and Northwestern around. Is it a sarcastic edge that adds character (to put it charitably) to people from the Northeast? Likely, but that can't be the whole story.

In my many searches through the vast expanse of crap - and I mean the good & the bad - on the internet, I came across the website of Paul Graham, a Computer Science professor, essayist and artist who is one of the partners at Y Combinator. His essay called "Cities & Ambition" suggests that cities "say" something about themselves and their inhabitants. A highly recommended read...as are a number of his essays.

For instance, he says that Cambridge says "you should be smarter." NYC says "you should be more successful/wealthy." The Bay Area says "you should live better." Silicon Valley says "you should be more powerful."

Whether or not you agree with exactly what Graham suggests for each city, he's on to something interesting here. I have been trying the past few days to think about what Chicago says. I have no definitive answers, but I think something along the lines of "you should live contentedly" might get at it. There's a simplicity implied in being content that is very much present here. That's not meant as any kind of slight: as anyone who knows me knows, I'm all about maximizing my personal happiness. But that covers the music, food, heavy drinking and friendliness with just a touch of "high culture" that really define the city.

So I'm curious, fair reader, as to what you think Chicago - or any other city - has to say.

And just for suffering though my lengthy diatribe, I'll throw you a semi-related bone: music from a favorite Chicago musician. Devin Davis's album "Lonely People of the World, Unite!" came out about 4 years ago and remains in steady rotation on my iPod. It's all completely self-produced and recorded (minus one or two instruments on a few songs) and it is, frankly, a masterpiece of simple, heartfelt, straightforward pop/rock. His influences are quite apparent throughout the album (name checking off the major classic rock bands & artists is easy to do as you listen), and I will likely go into much greater detail on him and the album at some other point, but for now, enjoy a sampling...

Devin Davis - Turtle & the Flightless Bird