Brooks Wheelan live @ City Winery, Boston, MA [03-31-25]

Did you see Brooks Wheelan’s special Alive in Alaska? You did? Good for you! Then you know it’s one of the best (THE best?) comedy special to come out last year. You might not know this, but he’s also a very cool guy. Wheelan has always been funny and with his new special continues to do so. I can’t remember the last time he was in Boston, but I think it was a Laugh Boston or something like that. Does that place still exist? Was Wheelan funny then? You bet! Surprisingly, he was the headliner at the first date of the Boston Comedy Festival. Was I gonna be there? You bet!

The venue is City Winery, and I get chills when I think about that place. Attending the show, I felt like I was returning to the scene of a crime, because last time I was there, it was for Mike Hanford. He was great, but my body was not. I felt a little off that night, which then turned into a week-long fever because it turned out I had pneumonia. I’m not blaming Mike Hanford for that, but then again, I don’t think his comedy has been scientifically analyzed for pathogens. It could be dangerous! But it was a good show, and I caught the City Winery at a special time, because shortly after that, they instilled the dreaded $25 minimum policy. For all shows, even if you go see a folk act, you better buy some sliders or have two beers and tip generously. I don’t think anyone is a fan of that, so there I was patronizing this place anyway, hoping that at least the performing acts would get a bigger cut of the money. Brooks, I did it for you!

The place was packed (yay for the performing comics!), which made me a little too hesitant to awkwardly come to the front and sit with strangers to see a comedy set. After all, I didn’t want to ruin the wedding venue vibe the City Winery had going, and the Shai-Hulud-esque rumblings you would hear on occasion (from the subway nearby) were enough of a disturbance, so that’s the best picture I could take. Wheelan performed for about an hour, with fresh material, and was, pleasantly, still in top form. He covered topics like family, politics, family politics and the significance of having a “family computer room” when you’re in your teens. I wasn’t just laughing, I was crying. And it wasn’t just me, looking around I could see others as well with their heads in their hands, holding back their tears. Wheelan is just one of those comics that can connect with audiences and tell stories in such a way that are both relatable and hilarious. He’s one of us!

I hope to see him again soon, and you better HOPE he comes to your town. If you do, make sure to tell him we sent you!

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