Thinking small pays off big at Thomas Middleditch, Ben Schwartz improv show

How did just two improvisers, Thomas Middleditch and Ben Schwartz, manage to command a sold-out Chicago Theatre crowd of 3,600 people? By performing on a small scale.

On Saturday night, the pair took the stage for an improv set, an intimate performance format straying from the theater’s traditionally high-profile comedy bookings. Last December Amy Schumer performed a two-night run and taped the sets for her new Netflix stand-up special. Big names Eddie Izzard and Bill Maher are slated for May.

The two certainly boast their own pedigree. Middleditch stars on HBO’s “Silicon Valley” as Richard Hendricks, a socially awkward tech geek who rockets to rock-star status when he codes a revolutionary file compression software program. Schwartz portrayed Jean-Ralphio Saperstein on “Parks and Recreation,” an aspiring social media influencer who reeked of desperation. He also had a role on the Showtime show “House of Lies,” which ran from 2012-2016.

For Middleditch, the show was a grand return to the town where “I cut my teeth,” as he said at the top. While in Chicago, Middleditch could be found at Second City and iO, spending time in training center shows and on a Norwegian Cruise Line for the former and as a staple of Improvised Shakespeare Company at the latter. He was capable of delivering witty one-liners, often referencing cartoons from the 1990s, while utilizing his slender and lanky physicality to roll around on the ground and imbue performances with kinetic energy.

Improv comedy rarely requires a background set, props or costumes (the three are traditionally big no-nos), and the stage on Saturday night reflected the form’s simplicity. The pair had no set to play with, only two thin black chairs standing center-stage. They wore headset microphones and dressed down; Middleditch wore a long-sleeved gray shirt and Schwartz had on a red-checkered button-down.

The mismatched scale of the show was not lost on the performers. “This is either going to be a great night or a story of Icarus flying too close to the sun,” Middleditch said.

The makeup of the audience afforded them some confidence. Schwartz expressed relief that they didn’t have to explain what long-form improvisation is, seeing as Chicago audiences are hip to the concept via the teachings of the late Del Close.

Though the crowd was spread across the main floor and far up into the nosebleed seats, the duo kicked off the show on an intimate and emotional note. The suggestion that would guide their improv took the form of a 15-minute conversation with a couple expecting a child in three weeks. Schwartz took the lead, expressing curiosity for the husband and wife’s feelings on becoming parents. The father worried he would not be a great role model and the mother expressed a desire to raise a child who was “not an ass—.”

Middleditch and Schwartz were afforded free rein of the stage but performed as if in a tight cabaret space, crafting situations that limited their movement. Most of their half-hour set took place inside a car, a husband picking up his pregnant wife from work as an unexpected kind gesture, masking the fact that he probably had cheated on her, or worse. Their inevitable fight took place on the shoulder of a highway, meaning they weren’t able to stray much past the car for fear of oncoming traffic. Later they parked on the side of a cliff, requiring they closely shimmy around the car to avoid plummeting off.

The duo deeply explored these close confines, free from the requirement to flesh out 50+ feet of unused stage. Middleditch gifted the car with a CD player and windows requiring a hand crank to roll down, even though the automobile boasted modern amenities like push-button start. Their set consisted of a single scene, meaning they had plenty of time to cut to the emotional core of their characters, like when the husband’s unnamed past transgression had the wife wondering if he had the capacity to be a steady and loving father.

Middleditch and Schwartz leaned into the improv savviness of the audience. They repeatedly switched roles, evident only by a small cross on stage or a hand atop a mimed pregnant belly. The speech pattern and inflection of each character was roughly the same, offering no hints as to which comic was playing which role.

The show further tested the audience’s attention to detail by including many callbacks, such as one based on a simple misunderstanding during the audience suggestion portion. The married couple had said they were recently back from a “baby-moon,” a version of a honeymoon for parents-to-be to engage in last-minute (relative) debauchery, but Schwartz had heard “baby moon,” as in a tiny lunar object. This small goof became a centerpiece for the show’s conclusion, and though the idea of a moon child is outrageous, Middleditch and Schwartz cradled the moon baby as they would a human.

The massive scale of the Chicago Theatre did not deter the duo from remaining grounded in intimate emotional moments.

Steve Heisler is a Chicago freelance writer.