Ryan Croft

What brought you to Chicago?

We moved for a few reasons. One big was because I wanted to pursue comedy in some kind of professional capacity I’m still figuring out what that means. That’s my main goal: pursuing a career somehow ultimately related to entertainment. But really, a big part of me just needed to get out of my hometown. I have a lot of friends in Oklahoma and I miss them but little else about that place. Except for some of the food. When the food is good there, it’s amazing. At times, it feels so small town that all of its wide open spaces and sprawling countryside can still feel cramped and suffocating. I got tired of just visiting the places I wanted to live. Oh, I also miss my dog, Sailor. We couldn't take him to Chicago.

Where are you from?

The Buckle of the Bible Belt: Oklahoma. More details in question 1’s answer.

What do you find challenging about living here?

Paying bills, haha. Chicago isn’t the most expensive city but it sure ain’t the cheapest. Everything here costs just a little, and some things cost a lot more than they do in Oklahoma but I guess it’s worth it. I mean, we are literally paying for a better lifestyle and as much as living paycheck-to-paycheck sucks, I’m really thankful that we had the foresight to build a savings before moving here.

What are some of the reasons you love it?

I love living in Chicago. This city is full of challenge and opportunity. There is more room to take creative risks here and a greater reward for doing so. This city is so full of raw talent and insanely creative people that it’s impossible to become complacent. I love Oklahoma but, creatively speaking, a little bit of talent was all it took to become a big fish in a small, backwater pond. In Chicago, I have to constantly improve myself or face every performer’s nightmare of losing people’s attention because there are so many more talented, creative people everywhere you look. That might sound like a nightmare but being around such an abundance of capable performers means, when I do well in front of an audience or my peers, I have truly earned it because I stood out among some of the best in the city.

Why do you stay?

I didn’t come to Chicago just to try something new, take a break from Oklahoma, learn some cool stuff, or whatever other reasons people give for eventually moving back to their hometowns. I have no intention of moving back to Oklahoma.

I don’t know if I’ll live in Chicago for the rest of my life but I do know this city, in which I’ve lived less than three years, in some ways feels more natural to me than the place I lived almost my entire life.

I don’t really believe in fate but I do believe that someone can be “meant to be” somewhere in that they find a place that moves, lives, and breathes with the same energy they do. Chicago’s pulse races through its L trains and alleyways with the same intensity my blood pumps through my veins and arteries. The low, chugging thud of the red line along the tracks beats in time with the thumping of my heart. I can feel this city in and around me like it’s apart of my very being.

How has community affected your time here?

Chicago, though a land of limitless potential and creativity, can also be a place of infinite loneliness without friends and family. Thankfully, since moving here, I’ve made friends who have basically become family. The Chicago comedy scene can be great, if you’re a famous or at least popular comedian and to be one of those, you have to have been around a while. The rest of us just try to get by as best we can and make comedy buddies – people we see at shows and maybe get together for birthday parties but little else. I’ve been fortunate to make some true friends – people whose comedy I like but whose company I also enjoy outside of comedy shows and open mic’s. Without them, Chicago can be a wonderful but very lonely place.

Can you speak into the creativity found in the Chicago community (specifically in the circle of people you spend time with)?

(Answered in 4)

When do you feel most empowered and comfortable in your own skin?

Other than when I’m sitting on the couch in pajamas with my wife and cats, watching King of the Hill on TV, the only time I truly, consistently feel like myself is when I’m onstage performing. That also counts when I’m offstage but still in some way creating or writing something that will be performed. Everything else often feels like I’m some alien wearing human suit – trying to adapt and fit in by going through the motions of what’s expected of a normal person. I think that’s why my wife and closest friends are all what the corporate industry refers to as “creative types.” That’s their code word for “weirdo,” haha. I don’t like to think of or refer to myself as weird but I’ve learned my human interactions can sometimes be very awkward if I’m not “on” in some performer sense or 3-4 drinks deep in a protective social bubble. Yet, for some reason, put a mic in my hand and a spotlight on me and I can talk to those same people and make them laugh for an hour.

Has living in the city affected your style and the way you approach your day-to-day look? If so, how?

My personal style is mostly influenced by my love of punk bands and my wife, a fashion industry professional who, when we were dating, once threatened to break up with me if I didn’t “quit trying to look like Nirvana became a ska band.”

If you're up for it, would you share a specific story about an encounter you've had in Chicago that has moved you/stayed with you?

One day, after only living here for about three or four months, I was wandering around downtown, somewhere a few blocks from where Michigan Avenue meets Lakeshore. I came across a huge crowd gathered around two men loudly arguing by the intersection.** An elderly Asian man howled into a megaphone for people to repent their sins and escape hell while a younger, Middle Eastern man tried with all his might to shout over the megaphone and ask why the street preacher’s god was the only way to salvation. Neither spoke the other’s language. So, the contenders found a common ground – shouting in broken English. As the dispute continued, the crowd grew from a few curious onlookers into a swirling, swelling mass until it spilled into the street and stretched into the grass of a nearby park. The air popped with electricity while also hanging heavy with intense, personal drama. It felt like something out of a stage play yet was happening right here, on the streets of Chicago. We weren’t merely bystanders or a passive audience. We were a sea and these men were the rocks against which our collective consciousness crashed. This might seem like an odd choice of story but something about the whole scene felt like the most Chicago-esque thing I’d ever seen. It was loud, brash, exciting, fun, and larger than life. Here were these two men with nothing in common other than a second language and passions so feverish that they left themselves with no other choice than to verbally slug it out in public and, much like an old school playground fight, we were all somehow complicit in this showdown. Some people were jeering and cheering it on while others wondered who was going to break it up. I can write and create and perform for the rest of my life and I'm unsure if I will ever come up with anything as hilariously dramatic and real as that moment.