A GoPride Interview

John Hill

John Hill slides into The Den for a Silk-y set

Sun. August 16, 2026  by Jerry Nunn

People are so nice to me in Chicago and the audiences are great.
John Hill

john hill

photo credit // the den theatre

John Hill selects Chicago for Silk and Loose!

The multitalented performer John Arthur Hill just touched down in Chicago with his new show, John Hill: Silk and Loose! While he has performed at The Den Theatre on Milwaukee Avenue in the past, August 16 marks the first time he’s on the Heath Mainstage.

Hill has a background on Broadway with The Boy from Oz and playing Fender in the original cast of Hairspray.

He served as producer for Watch What Happens Live, Project Runway and Top Chef among others.

Hill currently co-hosts Andy Cohen Live on SiriusXM’s RadioAndy channel 102 every week and he’s based in Los Angeles.

He left La La Land behind to tell his stories and sing songs on the road. After flying into the Windy City, Hill met up at The Den Theatre in Wicker Park to talk about his latest endeavor, Silk and Loose!

JN: (Jerry Nunn) The Den Theatre is such a historic space. I saw Jeff Hiller play here not too long ago.

JH: (John Hill) He’s from San Antonio, Texas, like I am.

JN: He was also gay and raised in the church too. I was also, but in Tennessee.

JH: What denomination?

JN: Southern Baptist and it was very strict.

JH: We were Church of Christ and it was worse. We weren’t allowed to have musical instruments.

JN: That’s such a shame because church music is the best part of religion in my opinion.

JH: They sing a cappella, but some of the independent congregations allow music now.

JN: When did you come out of the closet?

JH: I was 19 years old and a freshman in college. My parents found out, so I didn’t get to come out. They found an email about my very first boyfriend, which I talk about in the show.

JN: How did your parents handle the news?

JH: They struggled with it for a pretty long time, but they came around.

JN: San Antonio has an annual River Walk Pride Parade that I have attended several times.

JH: I haven’t been yet. I moved away from Texas for college, so I didn’t live there when I was out.

JN: Are you in Chicago a day early to rehearse the show?

JH: I don’t like to arrive the day of the show because of unexpected delays. I sat on the tarmac for two hours today.

I am happy to be here early and I have my dog, Pete, with me. People are so nice to me in Chicago and the audiences are great.

JN: For Silk and Loose! is there a lot of crowd work?

JH: No, not with this show. For the past three years, I did a solo show where there were fragments of this one and I saw what the audience would respond to.

I wanted to write a show that had a start, middle and ending.

Sometimes in the past I would do crowd work the whole time, so I wanted to do something that was written and rehearsed. That was my challenge in creating this show.

JN: Performing unpredictable improvisation in front of a crowd is easier than writing out a set?

JH: For some reason it’s easier for me to do that. If I have weeks before a show, it’s not on my mind to sit down and write something in the middle of the day.

I had to learn to plan ahead.

JN: On social media, standup comedians will post snippets of their sets, but in person they struggle with a longer set.

JH: I have noticed that. Even in high school, I would cram before a test because I didn’t like to study. I didn’t apply myself, so I hope this show is me applying myself.

JN: Who are your heroes in the world of comedy?

JH: Sandra Bernhard is the main one that I work with now. She really affected me as a teenager when I lived in San Antonio. I got a bootleg of Without You I’m Nothing when I was 15 years old. I remember listening to it and Tori Amos played on the acoustic piano. I knew at the time that I related to it and I wanted to do something like it one day.

Sandra and I ended up being co-workers at SiriusXM, which is crazy to think about.

Once I started doing solo shows, it was very Sandra-inspired and then I saw cabaret shows, which inspired me even more, so I started doing that.

JN: You could just tell celebrity stories as an act after meeting so many over the years.

JH: People sometimes expect the tea to be spilled, but I don’t usually write about that. I meet so many people at my job that I don’t think about it afterward. I don’t get starstruck often.

JN: If there were more queer people like Orville Peck singing in country music, do you think you would have stuck with it as a career?

JH: If I hadn’t moved away for college in LA, then I would have gone to Austin to be a singer/songrwriter. I was a little scared of traditional country, but I would have loved to pursue country music as a career.

JN: What is your all-time favorite musical?

JH: Sweeney Todd. It’s a fun show to be in and that music is really special.

JN: What are your plans for Silk and Loose?

JH: I just wrote the show and I am changing things every time I perform it. I have performed it in New York, Provincetown and LA. The shows have all gone great and I have learned a lot. I didn’t book too many dates to see how audiences respond and hear feedback.

I am performing the show in San Francisco and at the Catskills Comedy Festival, both in October. I am trying to get a Joe’s Pub date and then we will see…

JN: Chicago is a strong city for comedy, so playing here was a good choice.

JH: Boston and Chicago are my favorite audiences. People here were so supportive last time and they laughed at the right things. Some people don’t know when they can laugh at my shows at first, then they settle in and enjoy it.

JN: Is it tough being in a comedy as a sober person?

JH: Well, I got a lot of it out of my system when I was partying hard. I was a pill popper, so I would take opioids and tranquilizers.

It has been over five years since I stopped. I think my addiction was based on unresolved religious trauma from the church. At the time, I didn’t know how to cope and I didn’t have the life skills that I have now.

JN: How many podcasts are you currently on?

JH: I used to be on Discretion Advised with Marc MacNamara and that lasted for four seasons. When I signed on at Sirius, I wasn’t allowed to do other podcasts.

Andy Cohen and I are live on the radio from Monday through Thursday. The team packages our best moments of the week for the final podcast every Friday.

I am grateful for people who have listened every day for the past 10 years. I talk about very gay things from my perspective, so I am always surprised that there are so many female listeners.

JN: HBO series Heated Rivalry did very well with straight women.

JH: With this current standup show, it leans into being graphic and I wonder if some of the audience understand what I am talking about. I can be raunchy, but I am not trying to turn people on or be provocative. It is just normal to me.

JN: Are you filming the show?

JH: I am. This Silk and Loose is inspired by Jacqueline Novak’s show Get on Your Knees. Her one show was relentless and rapid fire about a blowjob where she barely took a breath. She performed the show here at The Den Theatre.

JN: I interviewed Guy Branum backstage here and he used slides during his set.

JH: I use slides too. I made one show that used like 80 slides, but this one uses just a few.

JN: Do you have music?

JH: I sing one song that I wrote for the show, but I might swap it out.

JN: This tour sounds like a work in progress.

JH: Yes and I want the show to be as good as possible, so I am open to trying different things while on tour. I hope everyone comes to see me in Chicago!

Keep up with the current tour at johnhill.online and follow his radio work on SiriusXM.

 

Interviewed by Jerry Nunn. Jerry Nunn is a contributing writer to the GoPride Network. His work is also featured in Windy City Times, Nightspots Magazine and syndicated nationally.

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