Chicago a cappella. Image by Kate Scott Photography
Chicago a cappella. Image by Kate Scott Photography


For decades, Chicago a cappella has entertained audiences with its ensemble singing, as the 10-member group blends entrancing voices with engaging personalities. On May 28, the group puts on its annual “Cabaret Night” a fundraiser supporting the organization’s artistic and educational programs.


Chicago a cappella Executive Director Matt Greenberg. Photo by Jeannie Liautaud Maul
Chicago a cappella Executive Director Matt Greenberg. Photo by Jeannie Liautaud Maul

Executive Director Matt Greenberg recently talked with Windy City Times about several aspects of the organization, including harmonizing and auditioning. However, he also talked about the show, his dream guest artist and what it means to be part of the LGBTQ+ community.

NOTE: This conversation was edited for clarity and length.

Windy City Times: I was in high-school choir for a few years and that’s it regarding my musical background. What’s your musical background?

Matt Greenberg: Yep high-school choir rings a bell. I started taking piano lessons when I was a much younger kid, and got into choirs and never stopped. I went to college to study music and became a professional singer once I moved to Chicago after college. I then sang all over the place the Chicago Symphony Chorus, the Grant Park Chorus, musical theater. 

And when the founder of Chicago a cappella started the group, I became one of the singers; at that point, it was a group of nine. I sang with the group for many years, but only a few years after the group started, the founder looked for someone to help with the administrative side. So I came on and, pretty soon, I was being called executive director and here we are 30 years later.

WCT: I’m curious: Since you have such an extensive background in voice, are there misconceptions about singing? I’ve heard things like to avoid dairy products and to rest your voice if you’re performing later in the day.

MG: I think those things are probably true. Unlike instrumentalists and other musicians, singers are using an internal organ their larynx to make their music. So some singers have a reputation for being a little quirky in that way. They have their phobias and things they do or not do before a performance. Most of it is based on reality; people have different physiologies, but there are some things that are not just as healthy.

WCT: Please tell our readers about Chicago a cappella. I know that people are becoming increasingly aware of them, whether they’re nationally known groups like Pentatonix, or local ones like Straight No Chaser.

MG: We’re a group of 10 singers (men and women) who perform with no instruments and no conductor. And unlike what most people think of a cappella music popular groups like Pentatonix and the movies like Pitch Perfect we certainly delve into pop music, but all of our singers are classically trained. Many of them can be seen at all the big concert venues around town, so they’re the top professional singers in the city.

But what sets us apart is that we come together and sing all styles of music, and we try to do those in a respectable and authentic way. So we really don’t want to sound like a bunch of opera singers who sing an Elton John or Beatles song. We sing vocal jazz music. We sing everything, and it’s that variety that keeps audiences interested and coming back. Generally, our concerts are programmed around some kind of theme and we often have guest artists, dancers or storytellers.

WCT: And the joy of ensemble singing is for everyone, as your website says. However, the talent for ensemble singing isn’t with everyone. [Greenberg smiles.] What’s the audition process like?

MG: It takes a special combination of talents, I would say. We do auditions every year; we want to hear new singers and our current singers have to sing for us every other year. It’s a pretty high-pressure situation and it’s like singing without a net. They need to not only have great vocal ability, but they also have to have great musical ability. They have to be able to read music fluently and sight-read very well, so they can learn the music very fast. They have to be able to hold their own voice, obviously. And they have to have a real understanding of styles and languages, although some of that can be taught. Also, listening is probably the greatest skill our singers can bring. 

They have to be able to be wonderful solo artists. But they have to be able to be interested and attuned to that ensemble feeling and that’s not for everyone. There are some singers who enjoy the spotlight to such an extent that they’re not interested in blending in. Our singers enjoy doing both.

WCT: And this is more about harmonizing than singing in unison, correct?

MG: It is although unison singing is sometimes more difficult, especially if you have two people in a part. Having one person or three or more people can be easier. We’re generally not singing in unison but, when you do, it sounds easier than it is.

WCT: And what can people look forward to with “Cabaret Night?” What artists will be covered?

MG: It’s totally unlike anything else we do, because this is the one night of the year when it’s not so much about ensemble singing. It’s a fun free-for-all in which our singers come together and show off their solo chops. Our audiences feel they get to know our singers, who bring their own selections to this. It’s kind of self-curated in that way.

I was just looking at the [song] list. Let’s see: We’ve got a Sara Bareilles song from Waitress; something from Stephen Sondheim’s Merrily We Roll Along; a song from Wicked; a song from one of my favorite musicals, The Drowsy Chaperone; the Billie Eilish song from the Barbie movie that’s sung by a man; a Fleetwood Mac song; a 1930s tune by The Ink Spots; and something from the TV show The Family Guy. So as you can see, it’s all over the place. 

It’s going to be a blast. I’m getting more excited just talking about it.

WCT: If you could choose any singer to be an 11th member, who would you select?

MG: I certainly have a lot of singers who I love, but I’m not sure I’d want them in Chicago a cappella. Maybe Rufus Wainwright could be a guest artist. Or let’s think big: How about having Barbra Streisand come in and sing?

WCT: For you, what is it like to be part of the LGBTQ+ community in today’s America?

MG: That’s a deep one, Andrew.

My initial feeling is that I’m pretty lucky. I grew up in a time, of course, when it was not very easy to be gay but by the time I was 30, things were starting to change. I never dreamed that I’d be able to get married; the thought never crossed my mind. Now I’ve been happily married for so many years, and have been open and comfortable. Granted, I live in a city with other like-minded people, and I feel like I live in a bubble sometimes.

But I’m from a small town and my family still lives in a small town, so it’s not like I’m not aware of it. And my husband is from a small town in Indiana, and I’ve been going there for Christmas for 30 years. I feel very lucky.

People have a lot of challenges that I didn’t have but I think I had challenges they didn’t have. I never had to deal with some of the economic and backlash discrimination that’s happening now. I feel that I have this comfortable, privileged, easy life that I didn’t expect to have but I don’t think that’s the experience of most people, especially in the LGBTQ+ community.

Chicago a cappella’s “Cabaret Night 2024” will take place Tuesday, May 28, at 8 p.m. at the Berwyn venue Fitzgerald’s, 6615 Roosevelt Rd. For more information or to purchase tickets, visit this link.