Chi-Town Comedy Chat: Deanna Ortiz 'Crushes' It With Conversational Comedy

Deanna Ortiz

Deanna Ortiz has been performing comedy in and around Chicago since she was 18. Her disarming ability to obliterate barriers between artist and audience has garnered her big laughs on stages across the city, including at The Lincoln Lodge, where she has been a cast member for the past four years.

“If I can have a connection with the audience, that’s what I really love about stand-up. When it’s like we’re all just hanging out together here in this theater, that’s the best. We’ve got some drinks, so let’s just shoot the shit and laugh,” said Ortiz of her approach.

In its 20-year history, the Lincoln Lodge has featured a pretty impressive list of alumni – Cameron Esposito, Kyle Kinane, Kumail Nanjiani to name a few – and 2020 finds the comedy showcase reaching new heights with a 12-member cast performing in a new venue on Milwaukee Avenue. Ortiz is thrilled with the many ways Lincoln Lodge’s new home will help to nurture even more comedic talent in Chicago.

“We just opened at the end of January. We’re just starting to see what the potential is now that we’ve had about a month of shows. I’m really excited for it because we went from the back room of a pancake house to a rock bar to a theater in Wrigleyville. Now we have our own space and we’ll be able to do exactly what we want to do with it,” said Ortiz. “It has three theaters, so we can be doing three different shows at once. We have more classes available on top of Stand Up Seminary and Fem Com [Feminine Comique]. We have sketch writing classes and topical issue classes and a bunch of stuff. We’re able to branch out much more.”

As a teacher at Lincoln Lodge, Ortiz enjoys making the comedy world more accessible for newcomers.

“It can be daunting, especially in a big city like Chicago, to find a good open mic and go up. These classes give you a sense of community. They give you those first couple of steps to let you know that you can do it and how to get started because that’s always the scariest part,” said Ortiz. Her participants add to her enthusiasm towards the craft. “Teaching kind of reminded me, ‘Oh yeah, this is fun.’ When people take a stand-up class they’re excited to learn. Comedy is so fun, and it’s not just people complaining in the back of a bar at 2 a.m. It’s been really great. I really like teaching.”

Any time she can connect genuinely with people, Ortiz is happy. Her comedy is often seasoned with pop culture references – fun for everyone – and personal stories told in a way that makes you feel like each joke was written just for you.

“My stand-up is very narrative, and I like that I’m able to talk about my life and see who I can connect to with that,” said Ortiz. “The biggest advice that I have for other comedians – that other comedians have given me when I’m feeling kind of stagnant in my writing – is to go and do other things. Go to an open mic. Go to a show. Go see a play. Go hang out with friends and experience things outside of the back room of a bar. Do what everyone else is doing, that way you can relate to your audience more.”

Right now, Ortiz’s favorite way to juice up her creativity is by exploring everyday puppy love and celebrity infatuations on her podcast, Crushes! With Deanna Ortiz. The show features Ortiz and her guests dishing about everything from celebrity gossip to “the barista at your local coffee shop that remembers your name and your order,” but her favorite Crushes! segment is a game called “Hot or Just Tall.” “Hot” meaning hot and “Just Tall” meaning not necessarily hot, but very talented in one way or another.

For example, Ortiz explained that Dax Shepard was “just tall” because he just has a great wife, and Adam Sandler is “just tall” because he’s just funny.

“We play ‘Hot or Just Tall’ on Instagram, so it’s very interactive and what I love, love, love and I totally didn’t expect from this is no one has ever gotten only ‘Just Tall’ and no one has ever gotten only ‘Hot.’ Nobody has ever gotten 100 percent. Everyone’s opinions are different,” said Ortiz. “What I love about it is that every single person has a crush on somebody that you wouldn’t normally have a crush on. Everybody has a crush and everybody wants to be crushed on is kind of the slogan phrase of the podcast, and it’s so great to celebrate all the crushes that we have on everybody.”

Final Five Questions with Deanna Ortiz

What makes you laugh?

Right now the standard stand-up that makes me laugh is Lisa Traeger or Matteo Lane. They will always make me laugh. They are both so so funny.

Everyday things that make me laugh are just dogs in the wild. If you’re walking down the street and you see a dog pop his head into the window it’s just so surprising. Even a dog carrying a big stick is just so silly to me and that’s really making me laugh right now.

Whenever I see a dog like that I like to think about what I would want him to be saying and that’s just funny to me.

Do you have a favorite joke either that you do or you love from another comedian?

I really love Matteo Lane. During his late night set on Kimmel, I think, he talks about going to Starbucks and having them write his name on a cup. He gets the cup back and it says “Potato.” He goes into this whole thing where he’s like, “At what point do you say, I’m sorry but what is your name. This is the fifth Potato today.”

I’m butchering this joke, but it’s so funny. He’s a gay man and at the end of it he talks about how if there’s one gay man working at a Starbucks everything gets done, but if there’s two gay men working at Starbucks nothing gets done (Laughs). His accents are so funny. He really makes me laugh. I can watch that clip a hundred times and I have.

What establishments or landmarks would you recommend for someone to visit in Chicago?

Absolutely go to the Green Mill. On the weekend, go to Paper Machete at the Green Mill. It’s a great comedy show, but it’s not like a stand-up show. It’s in the middle of the day and it’s super fun. I think it’s one of the best run shows in Chicago. I think The Green Mill is a cool space to get a drink or listen to live music. There’s a bunch of late night taco places around there, love that.

Also the Woolly Mammoth up in Andersonville. That place is really cool. It’s a bunch of taxidermied animals and Chicago history. It’s a cozy little “if you blink you miss it” type spot. I really like that place.

I always encourage everyone to check out the other neighborhoods outside of downtown. Downtown technically is Chicago, but it’s not. Come up north. Go to Logan Square. Go to Bucktown. Do something else.

Do you have any comedy recommendations to share with the world?

Besides the Lincoln Lodge, Chicago Underground Comedy on Tuesday nights is a great show in the city that is consistently great. I think that was Kumail Nanjiani’s show when he first started stand-up in Chicago. There’s the big shows in Chicago like Comedians You Should Know, Lincoln Lodge, Zanies and Laugh Factory and a lot of people seem to forget Chicago Underground Comedy in that list. I think it’s a great show and it showcases a lot of newer and independent alternative comedians.

What makes you Rebellious?

People telling me what I cannot do. That makes me very, very rebellious. I just think of when I was young and my parents wanted me to go to college. At first I wanted to go to culinary school and then I backed out of that and my parents were like, “You have to go to a university.” I said, “I don’t want to do that. I’m going to do this.”

I think the older I get, the more I’m like’ OK I can’t listen to anybody else.’ Or I don’t want to, maybe that’s the thing (Laughs).

(Photo by Trainman Photography courtesy of Deanna Ortiz)

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Laurie Fanelli is a Chicago-based writer and photographer who specializes in live entertainment coverage. She is at home at major music festivals like Coachella, Bonnaroo and, of course, Lollapalooza and Riot Fest. She loves chatting with hilarious comedians and has interviewed the likes of Maria Bamford, Paula Poundstone and Tracy Morgan, to name a few. She has photographed tons of great bands/musicians – from every genre – including Rob Zombie, Florence and the Machine, Alabama Shakes, Neil Young, Shania Twain, Pitbull, Pierce the Veil, Kendrick Lamar, Patti Smith and many, many more. When not writing or shooting shows, Laurie loves to spend her free time training for marathons and exploring the city of Chicago. She is a longtime vegetarian and animal advocate who likes to cook healthy, delicious meals that everyone can enjoy. For more information or to contact Laurie, head over to