Singing Since She Can Remember

Jazz singer Tracye Eileen on her unusual career path

Tracye Eileen is living her dream. At eight years old, too shy to act in the school play, her teacher asked her to perform one of the play’s songs. From there, she caught the singing bug. Fast forward to today: Tracye has a label, Honey Crystal Records, and a residency at Buddy Guy’s Legends in the Loop, where she performs monthly jazz and blues sets. And last Sunday, she celebrated the release of her newest album, WHY DID I SAY YES. The Weekly sat down with Tracye Eileen to talk about her new music and career. This interview has been edited for length and clarity.

Listen to the full version of this interview that aired on the May 15 episode of #SSWRadio, the Weekly’s radio hour on WHPK:

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Are you from Chicago?

I am indeed from Chicago. Grew up in Chatham, and while in Chatham I attended [John T. Pirie Fine Arts and Academic Center], and that’s when I had my first performance at eight years old.

And what did you perform? 

I sang “Somewhere Over the Rainbow.” I auditioned for the role of Dorothy, [but] I was just too shy, I just couldn’t make myself sound loud enough to get that part—but when I sang, it was just, you know, the faculty was just floored. And so ultimately what they decided to do is rewrite the play and have Dorothy go to sleep, and then I’d come in as a fairy godmother and sing “Somewhere Over the Rainbow.” That was my first performance, but I’ve been singing ever since I can remember.

And how old were you?


From there, how did your musical career grow?

I went on to perform in the jazz band in high school, and then I went to Jackson State University [in Mississippi]. I was with the jazz band, the JSU Singers, and my plan was—some of my classmates went to California and did very well [in the music industry]—but I decided I would would go and get my MBA and go work for finance, and get discovered somehow by working at [a] recording company. But I got sidetracked, and I didn’t do that, and I continued to have a corporate career—but I always continued to sing. I sang in the women’s chorus at Trinity [United Church of Christ in Washington Heights] for over thirty years. I sang in gospel groups, sang at weddings, funerals. And I actually got to do a ten-city gospel tour [in Switzerland] as a soloist with Trinity’s women’s chorus as well. So it’s always been about that.

In 2009, I got divorced, and so I decided I would pursue what I really wanted to do, which was to sing. I studied jazz, going from an amateur to professional at the Bloom School of Jazz in a little over a year. And then the owner of the school helped me get started, and he put together a band, most of which are still with me today. They’re very accomplished Chicago-based musicians, they’re awesome. And then my first gig was at the Hollywood Casino in Joliet. And we’ve been going strong and growing ever since. 

The first songs that you sang were basically cover songs, correct?

Yeah. We do some traditional jazz tunes but, [along with] some of the R&B things that we do or contemporary jazz songs, they all are uniquely arranged, and so they all have that smooth jazz kind of feel to them. The first CD was all covers, and this CD, my second one, [the first single is] one of the songs I wrote. 

What’s the name of that song?

The name of that song is “Why Did I Say Yes?” It’s just kind of when I decided I needed to write, and along these years I’ve always looked for help and people that can advise me or give me some information, as well as doing my own independent research and figuring things out. One of the things I needed to know was how money is actually made in the industry, and how it’s actually made is you have to write. Otherwise you’ll be singing for your supper, pretty much. I want to do this until I can’t anymore, so I knew I was gonna have to write. In making the decision to write, I knew I would have to be self-revealing, so I had to make a decision that I would be okay if people knew my business. That’s where “Why Did I Say Yes?” came from, a love relationship that didn’t turn out so well. I love love, so a lot of my tunes are about love that’s gone well, or not so well, or just the different facets of it.

Since 2009 when you started this journey, what challenges did you have to overcome? 

The most challenging [thing] for me has been balancing my day job and the music. And, you know, it’s like I’m right at a point where they both are like one hundred percent, and it takes 200 percent of my time, so I don’t really have room in my life for anything else right now. It’s a difficult business. I think had I done this at a much younger age, [it wouldn’t] have been a good thing for me. It takes a lot of resources, and I’ve been blessed enough to be able to finance my dream. A while ago I downshifted in my cost of living so that I could just pour as much of my resources and myself into my music as possible, and it’s paid off.

Have you had your big break yet? 

I think I’ve had some nice smaller breaks along the way. Some of them were opening up for Babyface, Mary Wilson, Chanté Moore, the Stylistics—those were all amazing opportunities, but probably the most significant one would be playing at Buddy Guy’s. That’s a stage that’s desired by musicians all over the world, very famous musicians and [non-famous]. I was actually discovered by the booking manager, who’s now my talent agent, Mark Maddox. He heard me on LinkedIn, found me on LinkedIn. How unusual is that? My ultimate goal is to be an internationally recognized jazz and soulful R&B artist, and so far, things are on track.

Tracye Eileen performs monthly at Buddy Guy’s Legends, 700 S. Wabash Ave. (312) 427-1190. She will also appear at the 57th Street Art Fair, between Dorchester and Kimbark Avenues, from 4:15pm–7pm on June 2.

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Bridget Vaughn is a producer for SSW Radio. She last contributed a series of interviews from the 2018 Women’s March in January.

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