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Updated: Nov 3, 2018

For the past couple of years vocalist Alyssa Allgood has been very busy and it doesn't seem to be slowing down anytime soon.

She kicked off 2016 with the release of her critically acclaimed debut recording Out of the Blue which landed her a performance spot at the 38th annual Chicago Jazz Festival. The next year she won the prestigious Ella Fitzgerald Jazz Vocal Competition and continued building her name on the jazz scene both locally and nationally through club and festival performances and now in 2018 she has released her sophomore debut recording Exactly Like You on Cellar Records, finished a tour of the Midwest and has performances coming up at the legendary Green Mill Jazz Club November 9th & 10th.

We caught up with Alyssa to talk about how she got started in music, her influences, the new recording and what she has coming up for 2019.

1 When you were growing up tell us about how you were first drawn to music? Did you grow up in a musical home?

I’m not sure what initially drew me to music, but I have been involved in it ever since I can remember. I started singing in elementary school and received my first big break (kidding of course) with a solo in third grade. I continued participating in my school music program through high school and sang with the jazz band, participated in musicals and several choirs. I’m grateful for the early opportunities to explore my voice and possibilities with music.

My parents have always been supportive of my involvement in music and big music lovers themselves. My dad is a big blues fan and I have memories of us singing and dancing to Aretha Franklin when I was a kid. My mom was a jazz fan and I remember listening to jazz recordings with her in the car and going with her to see Kurt Elling perform.

2 Was there a person or experience that drew you to start singing?

I mentioned my involvement with my school’s music program at a young age and I think that really instilled a deep sense of love for music and performing early on. I began singing with the jazz band in junior high and had many opportunities to sing as a soloist. I continued singing with the jazz band at the high school level. My teachers’ support and encouragement was really invaluable to my development as a student and person and inspired me to continue on a path of music.

3 What college did you attend and what was the reason for your choice?

I went to North Central College in Naperville. I started attending Janice Borla’s Vocal Jazz Camp when I was 12 years old and I attended it for many summers following. I learned a lot from her and Jack Mouse during that time and wanted to continue studying with them in college. My experience was very centered around vocalists learning and performing like instrumentalists and that helped me have an understanding of what it takes to be as prepared as anyone else on the bandstand. I’m certainly grateful for that message and think it has made a big impact on me as a professional singer.

As you were honing your craft here in Chicago, was there any specific musicians that influenced you and helped you develop your sound?

I have been influenced by many of Chicago’s great jazz musicians and take away something new each time I hear someone perform. My ultimate goal as a jazz singer is to communicate an authentic and honest version of myself in song and I pay close attention to how other musicians do that. I am inspired by observing a musician’s stage presence, what kind of repertoire they choose, what kind of stories they might tell, and how all of that makes me feel as a listener. I take those observations and bring them into my own practice. I spend a lot of time shaping and developing these elements from my own perspective and story.


Over the years you have competed and placed in the Sarah Vaughan International Jazz Vocal Competition, the Luminarts Cultural Foundation, Mid-Atlantic Jazz Voice Competition, Ella Fitzgerald Jazz Vocal Competition, Shure Montreux Jazz Voice Competition and in 2017 you won the prestigious Sarah Vaughan International Jazz Vocal Competition. All incredible accomplishments. How did performing, placing and winning in these competitions help you with your musical career?

I am incredibly grateful for each of these opportunities and think they have helped me grow tremendously as an artist and performer. To me, a competition is like a hyper-concentrated performance setting. You have a very small amount of time to establish a connection with your audience and the judges and to show who you are and what you can do. These competitions helped me learn what I want to show about myself and how to prepare for a high-pressure situation. This is invaluable in terms of learning to channel nervous energy on stage, and continuing to figure out who I am as an artist and how I want to communicate that to an audience. These competitions all offer a varying level of financial prizes, which has helped me fund projects, including my debut album, “Out of the Blue”. An additional part of my prize for the Ella Fitzgerald Competition was an opportunity to sing with the Four Generations of Miles Davis Band at the Blues Alley in Washington D.C. I performed with Mike Stern, Jimmy Cobb, Buster Williams and Sonny Fortune to a sold-out crowd. Talk about needing to channel nervous energy and show yourself to an audience…it was a total blast and a performance I will remember for a lifetime!

6 You have headlined at many of Chicago’s premiere jazz clubs and it seems as if your schedule is constantly keeping you busy. What is it about the Chicago Jazz Scene that has kept a vocalist of your caliber in town and not moving to New York?

I have found a great sense of community in the Chicago Jazz Scene. I was met with a lot of support and encouragement when I first came on the scene and I continue to feel that today. There have been many people who have helped me navigate various aspects of the business, who have encouraged me to seek out performance opportunities, and who challenge me to continue to grow. I am friends with many great jazz musicians who I look up to and respect musically and I think that is very special.

7 Your new release entitled "Exactly Like You" is coming out two years after your debut recording "Out of the Blue". What was your motivation for this recording and what was the process you went through to select the tunes?

I was motivated to record this new album after meeting Cory Weeds and talking with him about the possibility of releasing an album on his label, Cellar Live. Cory is a great jazz musician and impresario based in Canada. I met him when he was in Chicago acting as a tour guide for about 30 people who were attending a number of jazz performances throughout the city.

I then started looking closely at what tunes I currently had in my repertoire that I felt drawn to record and explored new tunes that could round out the record. I recently started performing Charlie Parker’s “Yardbird Suite” as a ballad because I think the lyrics really lend themselves to that setting. I love singing it like this and have received a lot of great feedback from audiences so I felt like I had to include it. I saw Stevie Wonder perform a few years ago and was brought to tears when he performed “If It’s Magic” and I decided in that moment that I needed to record that one too. Each song on the album has moved me in some way or been an important part of my performances up to this point,

My debut album was a themed project and celebrated the classic Blue Note Records era. I chose not to do a theme this time so the songs come from many different songbooks. My goal with this record is to show many different sides of myself both musically and personally and I think the variety of repertoire reflects that. We have arrangements of vocal standards, instrumental standards, pop classics and originals.

8 As a vocalist, it is very important to work with musicians who understand your sound and what you are trying to create. Who are the musicians on the new release and are these all musicians who have worked with you regularly?

The new release features Dan Chase on Hammond B-3 organ, Greg Artry on drums and Kyle Asche on guitar. I have been singing with an organ group for a few years now and I absolutely love the energy, groove, and grittiness that is possible in this musical setting. I think it opens me up to explore different possibilities with my voice and expression.

Dan and I have been together for a little over 5 years and I think there is something very special about sharing music with your partner. We do a lot of playing and arranging together and spent a lot of time working on the music for this new record. The band is rounded out by Greg Artry and Kyle Asche, who are both incredible musicians. I had heard them both play in different settings and really loved their playing so I thought they would make a terrific band. We started working together to prepare this material and I am really happy to have them involved. The trio not only supports me as a singer, but plays with feeling and allows the music to develop in the moment.

9 Tell us about your upcoming performance at the Green Mill on November 9th & 10th. What can people expect to hear that evening?

I will have the band from the record with me at the Green Mill. We have had a lot of performances this fall so I’m feeling like we are extra polished on the material for the upcoming weekend! We will be performing all of the music from the new record, which is a mix of arranged standards, pop classics and original songs. The record includes music by Thelonious Monk, Lee Morgan, Stevie Wonder, Jimmy Van Heusen and more. Our group is rooted in the classic jazz tradition and brings a modern flair to the music with original arrangements and high energy performances. Our arrangements help tie all of these seemingly different songbooks together as we present them with new hits, grooves and feeling. People can expect to hear fun, swinging and heartfelt music.

10 What do you have coming up after your performance at the Green Mill?

I will be at Winter’s Jazz Club Thanksgiving Weekend (Friday, November 23rd and Saturday, November 24th) as the special guest with Chris Madsen’s Quartet. For our fifth collaboration at Winter’s we will be performing the music of Duke Ellington and Billy Strayhorn with an incredible rhythm section featuring Reggie Thomas, Dennis Carroll and Dana Hall.

I will be back at Winter’s Thursday, December 20th for a holiday concert with my good friends Rose Colella and Elaine Dame.

On Wednesday, January 2nd I will be presenting a New Year’s Concert at a beautiful new venue in Arlington Heights called Hey Nonny. And a little later down the road I’ll be performing Sarah Vaughan’s classic album, “Swingin’ Easy” at the Jazz Record Art Collective on Wednesday, February 6th. I’m already working on transcribing all of Sarah’s incredible scat solos from this album!

Visit for new on upcoming performances and recordings

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