Can you learn about the soul of a place by listening to people who are from there tell jokes? Not so much.
This year, Bridgetown's Best of the Midwest show stocked Analog Theater with comics who grew up, were born or spent a significant part of their lives in the same geographic region. Question is: Does that give them a unified identity? It is the contention of this writer, and non-Midwesterner, that being from the Midwest is not enough of a commonality to tie together a disparate group of funny people. That is not to say that Thursday's comics didn't share a lot of ideas.
Chief among the themes: Midwestern dining is sub-par. Ohioan Curtis Cook and Iowan Brooks Wheelan both mentioned Olive Garden and Red Lobster by name. Growing up in the Midwest led them to believe that these restaurants were fine dining. Realizing the truth was a formative experience for both men.

The cities are empty and the geography is lame. Jesse Popp, who hails from Michigan, brought up The D, a Detroit-themed Las Vegas casino that is so authentic that there are forty thousand abandoned slot machines. Janelle James, who says she "spent time" in Illinois, referred to the Midwest as a hellscape.
Finally, the politics: "It's tough to find out someone you love is a stupid idiot," says Brooks Wheelan of discovering that his own mother is a Trump supporter.
It is unfair to expect a group representing such a large percentage of these United States to have a whole lot in common. Beyond just being really funny, we can't expect these specific comics to somehow embody a Midwestern ethos.
Never was the fact that Midwestern comedy runs the gamut more obvious than in the evening's final two performers.
Veteran Chicago comic Bill Dwyer anchored the lineup. His Borscht Belt style was a ninety-degree pivot from the rest of the acts on the bill. In a room full of jokesters from Middle America, only the most seasoned comic had a bit about gorillas at the Cincinnati Zoo. Though some of his jokes didn't play super great to the modest Analog crowd, his set was the most polished start to finish and a reminder of why the Midwest is still a comedy powerhouse, and probably always will be.
But Brooks Wheelan stole the show. Performing second to last, Wheelan defied Dwyer's later claim that Midwesterners learn at a young age to hide their feelings deep inside. After a few minutes of jokes, the Saturday Day Night Live alum explained why he loves Bridgetown—it is the kind of festival where he can get drunk backstage, look at the Instagram feed of his ex-fiancée who cheated on him a month before their wedding, and then get on stage to talk about it.
Whether or not it was a put-on, it certainly didn't seem to be. Watching a visibly distraught Wheelan drunkenly rant about his ex to a crowd of maybe thirty kind-of-nervous, kind-of-sympathetic comedy fans is exactly what Bridgetown was built for. Even if the whole thing lacked classic Midwestern decorum.
Willamette Week