Sinisterhood in Chicago: Comedy comes to creepy curses

Sinisterhood in Chicago: Comedy comes to creepy curses
Sinisterhood's Heather McKinney and Christie Wallace

No one does Creepiness, Comedy and Camaraderie like Sinisterhood! A Q&A with Christie Wallace and Heather McKinney

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Heather McKinney first saw Christie Wallace in 2017 at an improv show at the Dallas Comedy House. In her lyrical Texas drawl, Heather told me, “I remember spotting Christie. She was a teacher. She was on all the best troupes. Seeing her perform, you’d go, “Man, I would love to perform with her. I’ll never get that chance!”

Heather is a University of Illinois/Chicago grad and honed her talent training and performing at Second City, iO, and the Annoyance. It turned out, Christie admired her back. She invited Heather to join her troupe and share the stage. But it would be months before they really cemented their friendship.

Fast forward to a spring day in 2018 when Christie created a Facebook post that would change both their lives. She was home with a newborn, binging TV shows. “One of them was The Keepers,” Christie recalled. “I was really taken with that series because they were solving cold cases. They were two older women who didn’t have any kind of training, but it was personal to them.” She wondered aloud to her husband Tommy whether book clubs existed where instead of reading, you sat around and talked “true crime, cults and creepy stuff.”

“I don’t know,” he replied, “but you should start that.”

Christie posted on the Dallas Comedy House Facebook page. Was anyone interested? “I’m definitely down,” wrote Heather. As Christie remembers, “We didn’t even know if there was going to be a podcast at first. We just met up. Heather happened to have a microphone and some recording stuff, and we recorded just in case.” The two continued to talk, get together and tape on a regular basis. Their conversations became the hit podcast Sinisterhood.  

Seven months after its inception, Sinisterhood broke into the iTunes Top 10 Comedy Podcasts and appeared as a Spotify Featured Podcast. A mere three months after that, the podcast hit one million downloads.  Appropriately, Christie and Heather believe they hit their stride in their thirteenth episode. It’s been an avalanche of downloads ever since – over 24 million and counting. The show has been featured in Marie Claire, Vulture, AV Club and Women’s Health and consistently appears on the Apple Podcasts Top Comedy chart.

On Wednesday, June 29 and Thursday June 30, Christie and Heather will bring Sinisterhood to Zanies for two unique Chicago-centric shows. On Wednesday, they pull back the curtain on Resurrection Mary, Chicago’s most oft-seen ghost. On Thursday, they will explore the legend of Cap Streeter, the renegade rapscallion who defied city politicians and police to create Streeterville literally from garbage. Both nights will be a celebration of the Chicago spirit in every sense of the word.

Christie and Heather are unique among podcasters. It’s not just that they’re star improvisers, though they are. Christie, in addition to being a life-long aficionado of true crime and the paranormal, is a mom and also pet parent to two dogs, five fish, one snail, and a “very sassy pig” named Petal who is known to make cameos during Sinisterhood’s live Q&As.

Heather brings a rare perspective as a licensed attorney who has performed pro bono work for the Innocence Project and represented victims of crime. She is passionate about making thorny legal issues easy to understand. They both love to solve mysteries and bring attention to injustice and the importance of changing local policies and voting.

Also unique, is the community that’s sprung up among Sinisterhood fans. Christie told me, “We’re most proud of the listener base that we’ve created. We hear all the time about how it’s the most supportive listenership of all the true crime podcasts. We’re very sensitive to the victims, their stories and their families. All of our listeners are very respectful of one another. We started the community, but our listeners built it. We’re there for our listenership. That’s definitely something that’s increased tenfold with the pandemic. We’re on tour right now and we hear, “You guys are my best friends. You just don’t know it.” And we’re like, “We think that you’re our friends, too!”

Christie and Heather kindly spoke with me by phone about their upcoming Chicago shows and how their friendship became a phenomenon.

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SINISTERHOOD’S ROOTS

Teme: What draws you to paranormal and true crime stories?

Heather: Growing up, I watched Unsolved Mysteries and I loved Beyond Belief: Fact or Fiction. Christie and I both like solving puzzles and trying to make sense of what we’re looking at. If we could be the ones to find the answer, that’s great. But even if not, we love the community and all our listeners. Like this past Friday, we had a story about a really weird situation. We put out a call to action and we’ve gotten a lot of possible answers.

Christie: I got a lot of my interest from my dad. He was very into creepy stuff like X-Files and aliens. I remember doing a book report in elementary school on the Bermuda Triangle, which was a book that we just had at our house. I was exposed to a lot of that and true crime. I think for me, the more I know about it, the more I can try and prevent that from happening to me, which is why I think women especially are into true crime. You feel like you have a leg up if you have seen other people’s stories and you can place yourself in those situations.  

Teme: What makes comedy a good partner for true crime and paranormal topics?

Heather: Well, we’re both comedians. That’s our background. From day one of the show, we’ve had a mix of topics between mystery, cults and true crime because we know that we’re going to have to ebb and flow with the comedy aspect of it.

For instance, when we did our three-part episodes on Ted Bundy, there’s zero comedy in that. But right after that, we did an episode on the weird clown spotting that happened in 2016 because that was really funny to us. We’re able to give ourselves and our listeners an emotional and mental break when we are covering tough cases so that they’re not getting burnt out week after week.

I also think learning how to laugh at yourself is part of self-care. We’re both really vulnerable on the show, and I think that’s why everybody relates – especially episode thirteen. Christie was extremely generous telling a story that most people would never tell anyone. Finding humor in what happens to us is a good tension release and the vulnerability makes people feel less alone which goes back to the community aspect.

We’re not ever making fun of anything to do with someone’s worst day. We’re really serious on those episodes. It’s like how you go to your friend with a really serious story that happened to you and also go to your friends with the most ridiculous, embarrassing story.

The mix makes the show a safe space. People may learn something. They may get really mad and upset and want to change a law in their town. They may cry because the story is so sad. Then in another episode or even later in the same episode, they may laugh at something very silly that one of us did. Like recently I called poison control because I thought I took too much anti-diarrheal medicine and was poisoned.

Christie: At the core of it, we’re storytellers and comedians. It would be really challenging for us to do a podcast where comedy didn’t come into it. So we found a way to intertwine the two while still being respectful and considerate.

HOW TO CHOOSE A STORY

Teme: How do you choose the stories you cover?

Christie: People can submit topics on our website. Heather created a very nice database by topic, so it’s very easy for us to say, okay, we did a true crime and it’s time for a mystery or an alien-type subject. Then we go and look at what’s there.

But first and foremost, we only choose subjects that we find interesting. If we’re really interested and we’re excited to talk about it, then we know it’ll come across, and others will be excited to listen. We don’t cover things just because it’s the hot topic right then. If we’re not interested or if we feel like it’s been exhausted and there’s not really anything to bring to the table, then we won’t.

We like to cover cases, especially true crime, where there is a call to action, where there might be some  law reform or perhaps it’s a missing person, and we’ll give out numbers to call if anyone knows anything to help solve the crime. Our goal is, one day, to solve a cold case. That’s why I wanted to start the whole thing in the first place.

A LIFE-CHANGING PODCAST

Teme: How has the podcast impacted your life?

Christie Wallace

Christie: This has been my passion for decades and to be able to do comedy and also legitimately help people feel better and bring attention to cases – that’s the dream. When we were on tour recently in Nashville, we were drinking Bushwhackers in a bar across from the Ryman Auditorium listening to a band sing Shania Twain at two in the afternoon, and Heather and I are just like, “We’re here doing research right now. How is this our job?”

Heather: We get messages from people all the time that say, “I really learn something when I listen to your show.” It’s a perfect thing if our work can teach us something and we can give [this knowledge] to our listeners. In return, we get this amazing community. Someone taught me how to use my inhaler over Instagram DMs because they were a listener of the show. I was so excited when I got to meet her in Raleigh at the “Meet and Greet.”  

Christie: Heather, you changed some beliefs, specifically one belief quite a bit.

Heather: That’s true. [The podcast] has made me a much more empathetic person. I used to be pro-death penalty. After we covered the Menendez case, I changed my mind. The more we get into the criminal justice system and the nature of human beings, we, and hopefully our listeners, try to look at everything with empathy. That’s something I learned from Christie. She’s got the biggest, best heart I’ve ever known. It’s not our place to forgive because we aren’t the victims, but we try to keep an eye on where somebody is coming from, and how did they get to the point that they’re committing this crime? And then is their life completely over based on the worst thing that they’ve ever done?

A WORLD-CHANGING PODCAST

Christie: Something that sets our show apart and has also changed my life and our listeners’ lives is that as a lawyer, Heather is able to explain all the legal aspects in layman’s terms so we all understand. She explains trials, or why one person was arrested and another was not. One of our listeners told us, “I learn more from your podcast than I did in law school.” We’re bringing awareness to cases and to what you can do to change things in your own hometown if you don’t like the way things are going. We’re always talking about how important it is to vote, especially in your local elections and to know who’s in charge.

Heather McKinney

Heather: A lot of times, topics interest us because an unjust thing happened. We have the opportunity to tell that story and talk about policy reform. We just did a three-part series on the murder of Betty Gore. Everybody is really mad at the outcome of that case. We can explain how the law was and how it evolved. If you think it’s unjust, who are you electing? A lot of this stuff is at the state level, and that’s the elections that people pay attention to the least. We’ll say, “This pissed us off. If it also pissed you off, you don’t have to just sit around and feel, well, we’re all screwed.” You can say, “How did we get here?” And then, “How can we change it?” That’s another way we choose cases. We see an unjust outcome and say what can we all do as a society to change that?

MANAGING HARD EMOTIONS

Teme: Sometimes when I’m reading a true crime story, I feel so sad. How do you deal with those emotions?

Christie: There have been several episodes where we’ve openly cried. That’s another reason that we don’t do only true crime. We need that mental break. The one that was hardest for me was the White Rock Machete Murder. After that one, we did a couple that were more light-hearted because we needed a mental cleanse after that.

Heather: Having a variety of topics helps us. We’ve both texted each other late after midnight like, “I can’t sleep because I’m looking at these photos” or “I’m reading these reports.” So I applaud anyone who can do this alone because I know I couldn’t do it without Christie.

Christie: Very much same.

Teme: Heather, you’ve described yourself as “easily startled and overly jumpy.” That’s me, too! What is your advice for just forging ahead with that constitution?

Heather: Improv really helped. I think the best lesson in improv is that someone has always got your back and Christie always has my back. If I’m going to do something scary, I jokingly tell her I have a little Christie on my shoulder. Something happened at my wedding where I needed to point out something that was not correct. I was like, “Oh, I’m afraid.” And then I just heard Christie like, “There’s nothing wrong with telling them what you wanted and being respectful and telling them how you feel.” And I thought, “I can do this!” The whole thing in improv is “Got your back!” We always say that before every live show and every improv show. So get a good crew, a good bestie and have somebody to look up to.

Christie: We’re both easily startled in the sense that people walking into a room can cause us to scream. My husband is constantly not doing anything wrong, just walking into a room, and I’m like, “Aghhh!” I think I’ve gotten more jumpy after the podcast probably because I read so much about these things. Tommy always asks, “Do I need to wear a bell?” That would help.

PARANORMAL VISITORS

Teme: Have you ever seen a ghost or had a paranormal experience?

Heather: Yes. I’ve talked about it on the air. In high school I saw what now I think was the “Hat Man.” The “Hat Man” is a ghostly apparition that people all around the world see. When I was eighteen, I was at my high school boyfriend’s house. A tall man in a kind of pilgrim’s hat or top hat walked up to the door and turned around and walked off. I thought maybe it was his stepdad up in the night to go to the bathroom. The next morning I asked the family, “Hey, was one of y’all standing outside the door, and were you wearing a hat?” They said to the younger sister, “Go get the photo.” She ran and got this Polaroid. It was a photo in that same doorway. A friend of theirs was standing in the doorway and over his right shoulder, it looked like a man in a hat. It could just have been the Polaroid was smudged or developed wrong. But they said that when they moved into that house, they had a lot of issues with the sound of bouncing balls and children’s laughter and some orbs coming out of the closet. They had a priest come and bless the bedrooms. Christie later asked me, “Why didn’t he bless the whole house?” Because this apparition seemed to walk freely in the hallways!

Also, my mom doesn’t like me to say this because she still lives there, but in my childhood home I would see a repeat apparition in the hall. It was like a person running down the hallway.  My dad before he passed actually mentioned, “Sometimes when I’m up late, I see that, too.” The previous owner of the home actually died in the home in a tragic accident. We couldn’t tell if it was his spirit or maybe his wife’s spirit because they were running towards where it happened. My dad just said that he felt like the person was in a rush. And I said, “Yeah, I felt that too.” I have always been open to talking about these things. I think that’s why listeners are happy to write in with their own experiences.

Teme: Have you ever received signs from a pet who has passed?

Christie: We have received several submissions where listeners have had cats after they’ve passed knocking things off the table or they feel like their dog’s sitting on their feet even though they’ve passed on. So it seems to be pretty common.

WELL, I TRIED TO FIND OUT!

Teme: If you could commit the perfect crime, what would it be?

Heather: We would never say on the record what it would be because we would get caught! Say it and forget it … write it and regret it! This is going to be written. So…

Teme: Good point.

Christie: Do not tell a journalist what our crime would be, probably.

Heather: Leave no trace.

Christie: Yes, exactly.

CHICAGO LORE: “SURELY, THAT’S IMPOSSIBLE!”

Teme: How did you decide on Cap Streeter and Resurrection Mary as the topics of your Chicago shows?

Heather: I was a tour guide at Sea Dog on Navy Pier, and those were two of the cases that we mentioned on the haunted tour. Of course, Chicago’s got a huge long history and a ton of legends and true crime. When we go on the tour, though, we usually only cover cases that are urban legend, maybe a haunting, because if we’re at a club called Zanies, we’re not going to talk about the worst day of someone’s life.

Cap Streeter is a whimsical, wild character. When you hear the story, you think, “Surely that’s impossible!” Actually, it’s very documented. It was a very wild case. It intersects with legend because he allegedly cursed the area. Then you bring in the “Hancock Tower Curse.” Then you also have the actual true crime aspect because he was breaking the law at the time and the police were coming in, trying to oust him.

Resurrection Mary is a quintessential Chicago ghost story. We love to choose topics where we can actually go and visit. We’ll go to the area where the legendary hitchhiking ghost has been seen and possibly to the bar where they leave the bloody mary at the end of the bar. I mean, it’ll be a really huge burden for us to go hang out in Streeterville and have a drink at the Hancock Tower, but we’re willing to do it for the show, I promise!

Teme:  What do these stories say about Chicagoans?

Heather: Chicagoans have a deep respect for history and tradition. Putting out a bloody mary for a ghost may seem silly, but better safe than sorry, right? And Christie is our bloody mary expert and aficionado.

Christie: I love bloody marys. I’m very excited. I’m going to ask them to make me one exactly how they make it for the ghost.

Heather: The Cap Streeter legend says, I think, that Chicagoans love to forge their own path and blaze their own trails and say, “This is how my neighborhood’s going to be!” I love Chicago’s different defined neighborhoods. Both legends are indicative of who Chicagoans are, and it’s no secret that it’s one of my absolute favorite cities, if not my favorite city. Don’t tell Dallas!

Christie: I did not go to school in Chicago, but I’ve spent a lot of time and it’s also one of my favorite cities. So I’m very excited to go back and spend some time there, see some friends and do some fun shows.

Teme: What can you tell us about these two stories now without giving too much away?

Heather: The fun part of our show is that we really research the history, but our show is improvised. So we don’t know the jokes yet because we’re going to improvise based on our experience in the city and what happens. That’s the magic for audiences going to both shows. We’re doing two completely different nights. You’ll hear two different stories and two different sets of jokes. The magic of a live show is being there and interacting with the crowd. We love to get local input. So you just have to be there.

PERSONAL CHICAGO CONNECTIONS

Teme: Heather, what is your most Chicago memory from the time you lived here?  

Heather: When I worked at Seadog, I’d get there early in the morning and have breakfast from the Goat at the end of the pier, then sell tickets all day or ride on the front of the boat doing a 75-minute architectural tour. I would do the 11:15, 1:15, 3:15, 5:15 and 7:15 tours. Talking on the mic back to back to back, improvising with the crowd, and interweaving history and humor together, has been really helpful in my current career path. Getting to teach about history and sometimes creepy stuff, but also making people laugh – that was my favorite. Even after having a drink at The Goat, hanging out with the folks afterwards, and going home, you’d go to bed and your body is still rocking back and forth because you were on a boat all day.

Taking in so much history and being able to tell the stories of a city that I really loved during the most beautiful summers is my most Chicago memory. I hope Chicago summers are as wonderful as I remember because I remember them as the absolute best. It’s 100 degrees here. I miss the boat life! And just eating all the wonderful Chicago food, which I love very much and cannot wait to get back to.

TWO EXCLUSIVE NIGHTS OF ORIGINAL WINDY CITY CONTENT!

Teme: Absolutely anything else that we should add?

Heather: Come out to the shows at Zanies! Come to both of them because they’re about two quintessential Chicago stories, and both nights are going to be different. So if you got tickets to one already, grab tickets to the other one. They’re both going to be a lot of fun because Christie and I both have such a deep love for this city. I think it’s really going to shine through when we tell these stories. We would love to have everybody there hooting and hollering at us in person.

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Christie Wallace and Heather McKinney bring Sinisterhood to Zanies, 1548 N. Wells, Chicago, June 29-30, 2022. Tickets start at $30.00, VIP (including meet & greet) start at $75.00, 21+ 

Wednesday, June 29, 8:00 p.m. Sinisterhood presents Chicago’s Most Famous Ghost: Resurrection Mary TICKETS HERE

Thursday, June 30, 8:00 p.m. Sinisterhood presents The Curse of Cap Streeter TICKETS HERE

Learn more and stay up to date with Sinisterhood at: sinisterhood.com and on Facebook, Instagram, and Twitter.

Listen to Sinisterhood on Apple Podcasts, Spotify, Stitcher, iHeart

Stay up to date with Christie on Instagram and Twitter.

Stay up to date with Heather at heathervstheworld.com, Instagram and Twitter.

Filed under: Entertainment, Interviews

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