On Nov. 11-15, openly gay comedian Todd Glass will perform at The Den Theatre, 1331 N. Milwaukee Ave., with his show, Todd Glass: The Event of a Lifetime.
Described as one of comedy’s most original voices and celebrated by the late comic Norm Macdonald as “the comedian’s comedian’s comedian,” Glass has built a storied career. From a childhood in Philadelphia navigating undiagnosed dyslexia and severe ADHD to opening for legends like Patti LaBelle, Aretha Franklin and Diana Ross by age 18, Glass has appeared on everything from The Tonight Show to Stand Out: An LGBTQ Comedy Celebration.
Glass’ current show is a mix of stand-up, personal stories and original songs performed alongside a five-piece band of distinguished musicians and improvisors. Recently, Glass and the band sold out his three-show, one-night-only run at the 2026 Netflix Is A Joke Festival in Los Angeles.
Note: This conversation was edited for clarity and length.
Windy City Times: What are your thoughts about performing in Chicago?
Todd Glass: Everybody loves Chicago, and I haven’t been there in a long time. When I found out about The Den, my manager said, “This is right up your alley.” Gary Goldman and John Mulaney had really said great things about it. And so I’m in the smaller room; it’s Theater 2A. I’ve been doing lots of shows in smaller rooms, like at the New York Comedy Festival; the room held 60, and we did 13 shows.
WCT: In researching you, I saw one show from some years back in which you talked about a 12-year-old girl who had her arm bitten off by a shark. You added that you didn’t want to sound like a jerk, but you would basically rather have arms than courage.
TG: Can I tell you something? I’m glad you brought that up because you know sometimes you have old jokes, and I always tell people they don’t even have to be socially wrong. Comedians and people. I don’t think it means I was a bad person back then, but there are words you shouldn’t and don’t want to use. I hate that joke because I tried to sell it really well—but, you know, this is an amazing girl.
I could do whatever I want, but I don’t want to. I’ve changed, as a person. Maybe I have more empathy. Maybe I’m more sentimental.
But, yeah, I do remember that joke—and, truth be told, it wasn’t even my joke. My friend Bobby gave it to me.
WCT: But is there anything in comedy that’s off limits now? Or are people too sensitive? Because Joan Rivers, for example, was someone who didn’t seem to care and approached just about any subject.
TG: You know, we talk about this all the time. And I’ve been trying, in the last two years, to make my thoughts cleaner.
I think people have pushed back but, if anything, you can say more than you could ever say, if you do the research and rephrase. But think about what you could do. On The Tonight Show, comedians like Joan Rivers couldn’t say as much if they wanted to be mainstream.
Look at the sitcoms. You couldn’t say “toilet.” But Joan Rivers [eventually] broke down walls like a motherfucker. They were interviewing Norman Lear, who [produced] All in the Family. And he was asked, “You couldn’t do All in the Family today, could you?” They expected Norman Lear to go, “No.” But he said, “Good. It did its job.”
So maybe you couldn’t do what Joan Rivers does today—but maybe that’s all right. And that doesn’t mean she was bad for doing it. We move on, we change. But no matter what era you go to, there’s going to be brilliant comedy and, right next to it, shitty comedy.
And diversity is a favor to comedy. Whenever I go to clubs and I see all types of people, the crowds are always better because they’re representing the real world. But I think you can do more now than you ever could do in the history of comedy. There are more platforms and the landscape has changed—but I think comedy is in a good place today with younger comedians.
WCT: You mentioned diversity. To that end, do you think any comedian can deliver humor that’s racist?
TG: Oh, of course. You know that as well as I do. I know from being gay that I was homophobic. People can also be sexist.
I tell people, just to get a baseline, to name one thing in the last year that they thought was dripping in racism, sexism or homophobia. They’re not going to be able to. You know why? Most people don’t even know what racism is, for example. Someone might say, “How can I be racist? My CEO at my company just promoted a Black guy.”
I think it’s almost a fact that you can be in any group and be racist, sexist or homophobic. But Maya Angelou spoke on this; she probably isn’t right all the time, but I’m gonna bet Maya Angelou was right most of the time. [Note: According to A-Z Quotes, Angelou said, “There’s racism and sexism and ageism and all sorts of idiocies. But bad news is not news. We’ve had bad news as a species for a long time. We’ve had slavery and human sacrifice and the holocaust and brutalities of such measure.”]
WCT: We’ve been talking about the power of words. I asked a question on my Facebook page recently about how people felt about the word “queer.” I’m kind of curious about your take on that word.
TG: That’s such a great question because it conjured some things in me when people started to use that word. I don’t want to sound like Jerry Seinfeld, who’s always telling everybody what they should do. So I try to go out of my way to say that there are some things that you might want to take; if you don’t, then that’s what’s great about comedy.
I had a hard time with the word “gay” when I came out but I don’t now. I don’t want to be called queer, but I certainly don’t hate people who use that word. … The verbiage changes but I’m okay with it, at the end of the day.
WCT: I know you’ve talked a little about what the audiences can expect at your show, but give me a synopsis of what people can expect.
TG: Well, even though I have the band and it’s a big part of the show. I always go out of my way to say this: The guts of this show is stand-up comedy. The show has a lot of jokes per minute and it’s fun and rewarding.
It’s a very tight, polished show from the second you get in there. You’ll get into the room and you’ll look around; it will be dripping in swank and sexiness.
WCT: And it’s called “The Event of a Lifetime.” When I first saw that, I thought, “Wow—this is one confident person. But then I thought maybe you were going for irony.
TG: Well, I’ve always heard that term—”the event of a lifetime”—even when I was 19 and I’d open for Diana Ross, Patti LaBelle, George Jones, Aretha Franklin and Luther Vandross.
WCT: And how do you end up opening for all of these incredible musical acts? I never knew of a time when a comedian opened for a singer.
TG: I lived in Valley Forge, Pennsylvania, and there was a place called the Valley Forge Music Fair, which is now the Westbury Music Fair. It has 3,000 seats in the round. Sometimes they would call down to the comedy club that was in Philly—one of the biggest in the city. The owner would recommend comedians for certain acts.
My parents came to a Patti LaBelle show. She, in the middle of every show, would sing a song called “There’s a Winner in You.” She dedicated it to me and asked, “Where’s Todd’s parents?” It gets me choked up even now.
WCT: Is there anything you wanted to say in conclusion about your show or anything else we’ve discussed?
TG: [For more insight,] you can always go look at my Netflix special or maybe go look at my Instagram. There are a lot of sketches on there and you can get a vibe for what I do. But this show—I don’t take it lightly. This show is tight.
Todd Glass will perform at The Den Theatre, 1331 N. Milwaukee Ave., on Nov. 11-15. Tickets are here.