Any Chicagoan worth his or her weight in amor or ruckus will have a rooftop story for you. When I was a skateboarding teenager, I was obsessed with the city’s concrete floor, but a stylish man in his seventies, who I once crashed into somewhere on Wabash, put it into perspective for me. After I awkwardly apologized, he told me that he had spent his adolescent years trying to climb up the Water Tower and getting chased up rooftops by ex-girlfriends and cops. He handed back my battered skateboard and smiled, his eyes shining with introspective mischief, and told me that I should keep my head up and try it sometimes.

​Of course, years later, I learned that many boys and a good handful of girls during the Great Depression sought shelter and refuge on Chicago rooftops. While on wandering walks in the city, or on an occasional skate, I keep my head up and I often try to imagine them – stealthy orphans stealing up stairs, fire escapes, and ladders to find solace and to get a better view of their catastrophic and shimmering city. (It’s no wonder that the rooftops of Gotham City were originally based on Chicago’s.) Today, our city’s rooftop bombers, taggers, and artists chase the ghosts of these orphans and seek the same thing that they once did – refuge from the formulaic and often brutish world below. We could learn a thing or two from them.

For all of its efficiency and necessity, a rooftop is a place to go when you feel the need to escape or when you need a different perspective of the city – inexhaustible towers, a cerise sunrise, the unfading blue of our great lake – but it’s also a place to consider and reflect on high. A place to go alone and wander the labyrinth of your thoughts. A place to bellow an Odyssean verse. A place to cavort with modern history. A place to abandon memory. A place to slow dance to Sam Cooke (or, R. Kelly, depending on your skool!) with someone you love, or at least, someone you love at the moment. Of course, the best rooftops are the ones where you can get epically drunk, commune with the ridiculous universe, and party with your friends like rooftop deities. So, yes, for all their efficiency and necessity, rooftops end up attracting orphans and artists and lovers and partygoers and would-be-gods. Essentially, in the city of Chicago, a rooftop is a Dionysian institution of refuge.

One particular night, some years back, a few good friends of mine and I needed a little refuge. We had just spent the previous two days and two nights on a non-stop hyper writing drive in order to submit to Bravo’s Project Greenlight, a tour de force competition in which thousands of young men and women across our Hollywood blitzed nation produce and/or write a television show over the course of two days and two nights, which is to say that thousands of young men and women quietly suffer those two days and two nights away under the illusion of a generous and grandiose Hollywood. Ah! But this is America. We have deities wearing crowns of sitcom scripts and wielding swords sharpened by Tom Cruise’s very own chin! To only be them. So very worth it! Our sitcom was entitled Settling Up. Basically, it was about on-going divorce proceedings between an awesomely hilarious, weight lifting, Camaro driving slacker and his equally awesomely hilarious once-bra-burning, fight-the-power wife turned corporate leviathan. The pilot episode starts when their runaway son returns to Chicago from Taiwan with a beautiful, fish-out-of-water Taiwanese pop star only to discover that his parents are getting divorced! It was, uh, a commentary, or something, on Baby Boomers and love. Ok! I know. I know. Absurd. BUT. We had spent 48 hours writing the damn thing and we loved the damn thing. Trancelike Hollywood was clearly awaiting us…That is until one of us, in a sitcom-y inspired moment, accidentally erased our only copy. So, with the click of a mouse button and a resounding if not entirely despondent and un-ironic booooooooo, our great masterpiece disappeared into the digital netherworld. Devastated and exhausted, we did what fallen Chicago writers do best – we absconded to a rooftop party. And ended up ruining it. While a moderately pleasant and mostly hip crowd attempted to quietly watch a very hip foreign film on a gorgeous rooftop off of Division, we drank a good portion of their alcohol and yelled at wonderfully drunk and attractive people on the street, who were not on their way to a rooftop party, who were, in fact, concrete dwellers. We felt sorry for them. We invited them up, much to the chagrin and angst of our hosts. We danced with them. We told bad jokes. Really bad jokes. From the sitcom we had just written and lost. We mourned our loss. We yelled and high-fived and made impossible promises of stardom. We threw bottles at the flaxen half-moon and listened as they crashed somewhere off in the distance. Dionysus of the Rooftop had clearly seduced us with hallucinations of Hollywood and ruckus.

​We got kicked out. And the moderately pleasant and mostly hip crowd stopped inviting us to parties.

A few years later, I found myself with a friend of the host of that rooftop party. We were celebrating and, in part, grieving, the last evening of the infamous and jazzy, deep red music club the HotHouse. Sometime during the coral stained sunrise in a few hours, the doors off Balbo Drive would close, and like so many other things neglected by the constant metamorphosis of our city, the club would disappear into a maze of memory. To further our disremembering, we danced and drank up the last of the club’s offerings. And sometime during the night, a small crowd of us retired to the rooftop to enjoy the silvery breeze coming off the Lake and to talk. I don’t remember what we talked about, but I’m sure it was mostly about myth and family and politics, Chicago’s triumvirate, and the friend of the host of the Division rooftop party wondered aloud if I would ruin the good conversation by throwing bottles at skyscrapers. I smiled and told her that I would not. I told her that I had abandoned sitcom writing and was now focusing on bigger and better things – a stage sketch show featuring PBS’s Star Gazer Jack Horkheimer and a rabbi that pitched bad sitcom ideas to Hollywood executives. I also told her that with age I had found reservation and maybe even a little maturity. Something like that. She smiled sweetly; though, I don’t think she believed me. We quietly sipped our drinks and watched the city lights and from the street below we heard laughter, debonair laughter or the midnight laughter of the soon-to-be damned. Before long, someone pulled out a camera and was taking photos of Balbo Drive, and I thought offhandedly, or I am thinking offhandedly now (rooftops have an ethereal affect on me) about how Balbo Drive was named after Italo Balbo, the fascist Italian aviator who flew from Rome to Chicago for the 1933 World’s Fair, proving once again, as the Swedish born, Chicago sculptor Claes Oldenburg once stated, that Chicago has a metaphysical elegance of death about it. We watched the photographer and I promised for a third time that I would behave. I wanted to behave. The night was elegant and self-possessed and I couldn’t think of a better place to be in the world. I turned my attention to the sky and the lights of the stars were somehow fused with the lights of the skyscrapers, a primrose fusion like that from a Van Gogh painting, and the skyscrapers themselves, ones I had known my entire life, seemed poised to puncture the night in what could only be considered defiance of a mortal life.

Photo by interpunct on Flickr.