Cleveland comedian and radio personality Bill Squire isn’t a stranger to talking about tough topics. From his time as a Mormon missionary to his sister’s anorexia to his relationship with his trans son, Squire shies away from nothing—unless he’s keeping it clean for FM radio.
By day, Squire is the co-host of Cleveland staple The Alan Cox Show on iHeartRadio’s 100.7 WMMS. By night, Squire is talking movies, comedy, relationships, and whatever else he feels like with his The Bill Squire Show podcast co-hosts and fellow Clevelanders Tommi LC and stand-up AJ DiCosimo.
On November 22, Squire released his second special of the year, Pure BS, on YouTube and was kind enough to sit down with Paste not once but twice (I messed up recording the first time) to discuss the special, Midwest comedians, and what’s next on his comic itinerary.
Paste Magazine: Let’s start here: This is your second special in the last year, right? Bam Bam came out nine months ago?
Bill Squire: Technically, it was recorded in May of 2021 and released as an audio album first, then we made a video special out of it for my YouTube channel, which is done pretty well. That was a clean special—and this new one is not. I just wanted to kind of have that juxtaposition where I can do clean, I can do dark, dirty. I like being able to check a lot of boxes.
Paste: Can you tell me a little bit about how you structured Pure BS, moving from the traditional joke setup to more story-based, and your reasoning behind it?
Squire: Yeah, I started with real dark, real punchline-heavy jokes, because I wanted to come out, really grab attention, and just kind of keep everybody on their toes—not really anticipate what they’re going to hear come out of my mouth. There’s a lot of people that really enjoy that aspect. But then there has been a little pushback from people not liking some of the subject matter because it deals with sudden infant death syndrome, and I talk about abortion and some of these things. Even when it’s obviously dark humor, there’s still people that it just does not go over with.
The idea is, if you watch the first two minutes of the special and you don’t like any of those jokes, I don’t want you here for the rest of it—I don’t think you deserve the rest of the material. Find something else; there’s so many options. Because it goes from a very jokey, dark special to something that’s pretty open and heartfelt at times. And we get to a point where I’m opening up about myself.
Paste: You have a very progressive stance on things a lot of people don’t think that Midwest comics, and the Midwest in general, would have. Could you compare and contrast the Cleveland scene and other Midwest comics you associate with to comics on the coasts?
Squire: Well, the comics on the coasts, a lot of the stuff that they’re doing, they’re preaching to the choir—a lot of the people in the audience believe very similar things to them. You know, they’re a little more insulated, and I’m performing for a lot of people that have very different opinions when it comes to things like abortion, or trans people, or trans kids. And they don’t necessarily want to talk about it—but I’m going to talk about it.
I’m going to talk about it in a way that I think is funny and constructive, not taking cheap shots. When it comes to talking about abortion, like, that’s not my business, but I do my business making jokes. So I’m gonna make jokes about it by saying something’s not really my business. And that’s kind of the point of the joke. I like to write the jokes that I write to, somehow, sneak behind people that disagree with what I’m saying and get them to think like, “Oh, I never thought of it like that.” I like that aspect of my joke-telling.
Paste: It seems like when those people are in the room with you, they’re on board—like, you get them on your side, you win them over. It’s only, maybe, online that you seem to get those keyboard warriors suddenly there?
Squire: Yeah, nobody says anything. Also, I’m a big guy—I know how to command a room. So like, I don’t get heckled. When I bring up these topics, no one has come up to me after a show and said the stuff that they say in the comments [online] when they’re talking about my son being trans or anything like that. It’s all cowardly people online.
Paste: The audiences in Cleveland that you’ve talked about your trans son to, they’ve all been pretty open to it, right? You’re not getting any, like, heckling about that, specifically?
Squire: No one’s heckling. Everyone’s laughing and they seem to be on board with it. And that’s why I get confused when people are so adamantly against it on YouTube and TikTok. And it’s part of what I’m doing, though, so I’m happy to at least get in their brain and they have to reconcile that they’re not right. They might never get it, but I hope that there are a lot of people that hear my jokes and understand, like, “Oh, this is something that’s real.”
I think, being a bigger [cis]male comedian, I’m not the one you’re expecting to go up there and stand up for trans people. But I do. The way Dave [Chappelle] did it…I thought it was lazy. That was just a really lazy stance that he took, I think there was some nuance that he thought was coming across, in a different way, but then there’s also the damaging part of it—calling himself a TERF (trans-exclusionary radical feminist). And his…not really understanding the science behind people that are trans. Genitals aren’t who you are as a person.
I think it was really disrespectful, the way he just tried to boil it down to a binary equation when it’s not. We have so much knowledge now and have so much to learn. And I think he completely missed the mark, on showing empathy to this really maligned group that is being taken down by—like, there’s so much anti-trans legislation that’s being put out into the world. A comedian going on stage and trying to stand with those bigots and be like, “Oh, they’re just jokes” doesn’t sit right with me. It felt real shitty.
Paste: Kind of in the same vein, you talk about Caitlyn Jenner, who has come out as anti-trans herself, but you have a joke—I don’t want to spoil it for anybody—but I thought you did such a good job of saying like, “Okay, well, this is her stance and why she’s famous. And it’s basically just being honest. So I’m gonna be honest with you all.” And it comes at the end, after you’ve done that joke-setup section, and we’re rewarded with this great story.
Squire: Yeah, I appreciate that you enjoyed that so much. Because it’s one of those things where—talk about being in Ohio—I talk about some things not everybody’s comfortable with. And I’ve definitely had that story fall flat and that feels real weird when you get to that point. Luckily for the tapings, everybody was great.
Paste: You’ve spoken about the Cleveland comedy scene, and how there’s a lot of people supporting each other. Can talk to you a little bit about that dynamic?
Squire: Yeah, the Cleveland scene is great because there’s such a broad spectrum of comedians, and it’s smaller. You’re all rooting for each other. And an example of this is Marcello Hernandez, who was part of the scene, and now he’s one of the newest cast members on SNL. And so when he got that, it felt really cool. Even though he’s been in New York for a couple years, he cut his teeth in Cleveland, and we’re just all super pumped for him.
I’ve accomplished quite a bit in my career, but I still do stand-up with someone that’s only been doing it for a few weeks, or maybe a few years, and they can learn from me, but I can also learn from them. Having that connection to the newer people is a good thing—it keeps me grounded and keeps me hungry. I see someone that’s new and really good, and that makes me really excited, because I go, “Oh, yeah, I gotta make sure I’m still stepping on the gas. So I can keep up with these newer people that are showing up and are really funny.”
Paste: You’ve mentioned before that you essentially talk for a living, between being on a radio show and a podcast and then doing stand up. Can you tell us a little bit about the radio show and the podcast?
Squire: I’d say my main gig is the radio show, just because we’re on for four and a half hours every day, from 2 to 6:30 in the evening.That’s The Alan Cox Show on 100.7 WMMS: The Buzzard in Cleveland, which is a legendary radio station across the country. It’s basically like four and a half hours of being in a writers room where Alan, me, Mary Santora, and Poundcake, who’s our phone screener, are all throwing ideas around and having fun.
And then my podcast, I get more specific on certain topics that I enjoy, which ends up being a lot of movies, or maybe, you know, Tommi, who’s on my podcast, is in the ethical non-monogamy community and so we talk about relationships and sex and things like that. We can get dirty there because on the FM radio, you have to keep things clean.
Paste:What’s coming up? What’s next for you?
Squire: I did this project in 2014, where I wrote 10 new minutes of comedy every month for a year. And now I’m going back through that and mining the jokes that I enjoyed and expanding on them for my new hour.
And on December 16th, we’re having Christmakwanzakah at the Agora Theatre in Cleveland, an amazing, historic theater. We did it in 2018 and 2019, then had to take a couple years off because of the pandemic, and now we’re back for the first time in two years. We’ve got a great lineup with Cleveland favorites like Mike Polk Jr., Mary Santora, John Bruton, and Jasmyn Carter. So it’s nice to have everybody around—we’re gonna do an awesome show.
Be sure to check out Pure BS on YouTube.
Brooke Knisley is a freelance journalist and comedy writer. She has balance issues. Let her harass you on Twitter @BrookeKnisley.