Susan Messing onstage with her husband, Michael Clayton McCarthy. Credit: Jerry A. Schulman

Susan Messing will always remember the opening night of her weekly show Messing With a Friend: that same evening Jack Farrell, a student in an improv class she taught, almost died from a ruptured aorta. As her student was rushed to the hospital, she took to the stage for her two-person, anything-goes improv show. “That’s how the real show opened up that night,” Messing says. “That’s how I remember when we started doing the show, because he almost died.”

Today that student is alive and well and working at Second City, and Messing With a Friend is celebrating its tenth anniversary. During the past decade the self-described “joyful, uncensored, and improvised romp through hell” has featured guests like Ike Barinholtz, Andy Dick (for a special one-off called Messing With a Dick), Aidy Bryant, TJ Jagodowski, and Rachael Mason. They take a single suggestion and create an hour-long, entirely improvised show. What ensues is a master class in improv: the performers play multiple characters and glide through scenes with such ease that it feels like the material must’ve been written ahead of time.

The tenth anniversary event will feature Jagodowski as the guest, with part of the proceeds from the ticket sales going toward the Nick Wieme Improv Scholarship, named after the improv comedian who died in the smokestack of the InterContinental Hotel in 2012. Jagodowski and Messing, who frequently collaborate together, have an objective they bring to every show they do: Jagodowski always tries to kill Messing, and Messing always tries to kiss Jagodowski.

“I bet she’s going to try to kiss TJ during the tenth anniversary, and I bet he won’t let her,” Mason says. “There’s a running over- under on how many times she tries to kiss him and how many times he tries to kill her. We all sort of bet on it—it’s riveting to watch.”

Messing, a staple of the Chicago improv community, came up with the idea of a weekly two-person event in 2006, when she decided to cut back from 11 performances a week to just one. “I got married and had a baby and thought, ‘If at most you could do one show a week, what would you want to do?’ ” Messing says. “I would want to work with people I had never gotten an opportunity to work with or I miss desperately.”

Messing With a Friend had short runs at Second City and iO before eventually finding a permanent home at the Annoyance Theatre—it’s now the venue’s longest-running show. The Annoyance’s executive director, Jennifer Estlin, came up in the local comedy scene with Messing: they first met in college at Northwestern University and were both cast during the Annoyance’s very first auditions. Despite their long shared history, Estlin was nervous the one time she performed alongside Messing as a “friend.”

“It was slightly terrifying, just because the last thing you want is to be the person who goes up with Susan and blows it,” Estlin says. “But she’s so wonderful about it. Her whole approach to it is, ‘If you’re not having fun, then you’re the asshole.’ It was a breeze—it was over before I knew it, and I had a really great time.”

Mason, who was a student in Messing’s improv class, likewise remembers feeling anxious before taking the stage with Messing for the first time. “TJ Jagodowski stumbled upon me,” Mason says. “He goes, ‘Don’t be nervous. Playing with Susan is like playing with a broken fast-pitch machine: you don’t know what speed or direction it’s coming from.’ And it’s still true.”

Since then, Mason has earned the title of the “friend” who has performed with Messing the most. The pair also make up the improv duo the Boys, and they’ve traveled the world together. The experience has taught Mason a lot. Messing “is a grown woman who still does bits in Customs,” she says. “You don’t do bits in Customs.”

The situation is indicative of what may have kept the show alive for so long: Messing lives and breathes what she does and enjoys doing it. She’ll run a bit into the ground if it delights her enough, and she says she’ll keep performing Messing With a Friend until she gets yanked off the stage.

“There is nothing better than to recognize that people have put down the joint, stopped tweeting or swiping right or left, and actually kind of share in what could be potentially magic or shit fire,” Messing says. “And they did it with me.” v