02/06/2013 06:09 pm ET Updated Apr 08, 2013

Making Out with Wes Perry and Friends at Upstairs Gallery Delivers Chicago's Best with Charm and Teeth

"This is what I came for," I thought to myself. Sitting in the third row in Upstairs Gallery, happily mashed into a vibrant crowd, I broke into a giant smile of gratitude. And like I do sometimes when I feel so full of corny, bursting, city-love, I whispered into the applause "I love you, Chicago."

On Wednesday nights, I can usually be found perched in the front row of iO's Cabaret Theater to watch my favorite team of improvisers, Virgin Daiquiri. But this particular Wednesday, circumstances conspired to keep me in my own neighborhood a few El stops north. So, with a mind to see some performance, I decided to accept a friend's invitation to Making Out With Wes Perry and Friends at Upstairs Gallery.

It was just one of those unexpectedly perfect Chicago evenings. Inhospitable weather to remind all of us out on Andersonville's stretch of Clark Street that here we make our own magic and don't need any help from the sun, thank you very much. It was the buzzing liminal time where some of us are wrapping up our days and others are cracking open the night. I love to walk alone on the street at this time. There are a million possibilities. And I can tell you that it doesn't feel this way in the Target parking lot in Central Michigan where I come from -- where I might be on this same night if I hadn't followed the inexplicable pull of this place on my heartstrings. "I love you, Chicago."

I arrived at Upstairs Gallery, buzzed and warm after an impromptu stop at Vincent to kill a little time (and a couple of Briar's perfect cocktails). Upstairs Gallery has certain slap-dash perfection in spades. A love-worn warmth that radiates from the sticky beer-pockmarked floor and the foam peeking out of cracked black pleather chairs. It feels like being in exactly the right place at exactly the right time; like luck. It feels like the fulfillment of that pull that drew me to Chicago.

And so in this buzzy blissed-out state, tucked in the bright, warm room, the show began and along with the rest of the audience, I met Wes Perry. I was dazzled, first of all, by his glittering lips, but he decidedly won me over forever when he delivered a charmingly deadpan monologue on global warming (complete with projection of inane but properly cherished screen images of blog comments), and then sang a truly beautiful rendition of "Stormy Weather." I heard the old standard anew. There are few things more reassuring to this audience member than a relaxed and capable host whose excitement to share a lineup of curated performers is infectious. And in this role, it doesn't get much better for me than Wes Perry.

Performer after performer came forward, sharing short pieces that masterfully blended comedy, theater, performance art, and that special shine and sharpness of Windy City teeth. A few standouts included Matt Leyes as the meticulously comported "Phyllis" negotiating with a spotlight, and Darling Shear, who promptly transformed the space into a church meeting and proceeded to bring the spirit of one Ms. Mariah Carey among us through wild and compelling lip synching and movement.

My favorite performer of the evening (in addition to Perry himself) was Irene Marquette, who wove public and private narratives to explore women's visibility in documented history. The piece began as a sort of hybrid letter/lecture with medieval literature as it's jumping off point, and culminated in a live song-and-dance-spectacular performance of Billy Joel's "We Didn't Start the Fire." Throughout, tallies were amassed of how many women were mentioned in the song as compared to men. Spoiler alert: not a lot of ladies, heaps of dudes. At the climactic lyric, "what else do I have to say?" Marquette stood resolved while pointing with outstretched arms at the literal writing on the wall. It was profound and uproariously funny. Laughing and crying, I soaked in the wonderful feeling of the room; of a group of strangers and friends, warm in the glow of great, honest work. "I love you, Chicago."

This really is a place where we make our own magic. Together, with whatever's handy, and most of all with a special brand of fearlessness that this audience member will always be grateful to live so near, we make great work, Chicago. If you're looking for an evening to confirm that you're in the right place at the right time, with warmth, smarts, teeth, and the jumbled perfection of laughing together, it's on Clark Street for the taking every third Wednesday of the Month, when Making Out with Wes Perry and Friends sets up shop at Upstairs Gallery.

If you're anything like me, the evening will leave you hopeful, with fresh gut-churning resolve to fling yourself into making your own contributions to your community, nurtured by the insightful and uproariously fun work of your neighbors. And as you walk the short distance back to your apartment, radiating that deeply fed feeling, you might find yourself whispering each visible breath into the bitterly cold snow, watching it dissipate, reaching it's warm, fluid fingers out, out, out as you renew your vow. "I love you, Chicago."