I have achieved a new level of comedy nerddom. I saw Tim Dillon headline twice in one weekend (Thursday and Saturday early shows) during his run at the Chicago Improv in lovely Schaumburg, Illinois. I have seen comics twice and even three times over one weekend but always in a showcase style show where they only do 20 minutes. This was my first time seeing the same comic headline twice in one weekend. I know I am an obsessive so my opinion only goes so far but I really enjoyed the experience.

I am sure the big question on your mind (other than why the hell would someone do this) is “was the material the exact same both nights?” The answer is “no”!

Here are aspects of the material that differed between the two nights:

• Dillon came out in a ridiculous outfit on Thursday, blaming an airline losing his bag for the loud getup

• Dillon allocates time to crowd work so on Thursday, he talked with an airline baggage handler and a realtor and made fun of the baggage handler for having that job and being a white guy with that job. On Saturday, he talked to two dietitians and ended up roasting the entire dietitian profession for well over five minutes. Somehow these interactions felt both spontaneous and sharply observant.

• On Saturday, he delved more into his Lizzo material and fat people, telling a story about venturing far to get ice cream with a member of the Chicago improv staff

• On Thursday, he started the set with his Ukraine war material and did at least five minutes more on the Ukraine war than he did during his Saturday set

Dillon’s material is a lot like his podcast. He takes political stances to a hyperbolic extreme and finds hilarity in ridiculous stances. But I have seen comics who have been touring a long time and they are clearly disconnected from the material, just rattling off the hour they have been doing for months in different cities to collect their paycheck. Dillon isn’t doing that. He is present with the audience, noticing and interacting with audience members, moving between prepared bits but clearly still working on the cadence, wording, and tags for his material. You feel like you are watching the creative process unfold on stage.

Watching Dillon live is an imitable experience because he has little moments where he shows he is noticing the audience. Near the end of the show on Thursday, Dillon said to a woman in the front row, “She’s been looking at me in disgust the entire show like SOMEONE PUT THIS GUY in a cage” and on Saturday, “I am all about these two blond ladies in the front row.”

Watching him do crowd work, I felt like I saw a nascent bit come into existence. The best material of the two shows was when Dillon roasted the two dietitians in the front row. He compared the profession to a drug counselor, riffing on the uselessness of both professions. I felt like I really got to see his mind work and I believe it when he says he doesn’t prepare for the podcast all that much. He just sees a news story and says what comes to his mind about it. I got to see him do that in real time, watching his eyes light up when he heard the word “dietitian” as he knew he was going to be able to go to town. If you want to see Tim Dillon’s mind at work, there is no substitute for seeing him live, ideally as close as possible.

As far as the material itself, it won’t surprise you if you’re a podcast diehard. He talks about Lizzo’s reality show, the war in Ukraine, trans kids and buying his daughter a premium dick, and other Tim Dillony things. But seeing it live takes it to the next level. There is no substitute for live comedy and watching a comedy genius do his thing in real time.

Beyond the laughter and an enjoyable night, there was a sense of privilege in witnessing a comic of Dillon’s caliber and fame perform in an intimate venue. Dillon just sold out Carnegie Hall and I got to see him in a 400-person club. I think part of the reason it was so easy for me to want to see him twice over the weekend was that I think these smaller-club days for Dillon have to be numbered. I felt really lucky to have the experience.

My review on seeing Tim Dillon headline twice in one weekend: worth it. He is connected to the audience and the material and you get to see the mind of a comedic genius at work. This isn’t fake business.