Jazz singer Alyssa Allgood shares lessons about self-love, vulnerability

Alyssa Allgood sings alongside saxophonist Chris Madsen
Alyssa Allgood sings alongside saxophonist Chris Madsen at Winter’s Jazz Club on January 8, 2023. (Antonia Mufarech/MEDILL)

By Antonia Mufarech
Medill Reports

It’s 7:30 p.m. on a Saturday at Winter’s Jazz Club in Streeterville. 

The lights dim as audience members sip a martini or glass of red wine. Tonight, saxophonist Chris Madsen joins vocalist Alyssa Allgood to celebrate the 1960s American jazz duo of Nancy Wilson and Cannonball Adderley.

Allgood walks toward the stage wearing all black. Her brown hair reaches her shoulders. Her rhombus-shaped golden earrings do too. Framing her face are turtle glasses with red temples that match her lips. She holds the microphone with her right hand and opens the show with Wilson’s “On The Street Where You Lived.” 


The 30-year-old’s scat singing comes naturally, with control over her vibrato that earns critical acclaim. As DownBeat magazine wrote in 2021, “she sings with a depth beyond her years.”

Like most jazz singers, Allgood croons about all things romance. But she also believes in self-compassion and understanding, which will play a prominent role in her upcoming fourth album. 

The lyrics are ready, and she is hoping to release the record on Spotify and other streaming platforms by the end of the year.


Allgood performs Nancy Wilson’s “On The Street Where You Lived.” (Photo Courtesy of Antonia Mufarech)
Alyssa Allgood performs Nancy Wilson’s “On The Street Where You Lived.” (Antonia Mufarech/MEDILL)


“Sometimes in jazz music, there’s this tradition of singers just singing standards, of redoing a lot of songs that other people have done, and that can be fun,” said Jon Deitemyer, Allgood’s friend and band drummer. “But I appreciate that Alyssa is writing music, that she’s challenging herself to actually take some risks. I think that’s actually more rare than people realize.”

Other than singing (with her piano or a quartet) at Chicago staples such as Green Mill Jazz Club and Winter’s Jazz Club, Allgood is pursuing her master’s degree in jazz studies at DePaul University, where she is also a graduate assistant. 

She teaches private voice lessons through her Allgood Jazz Studio and presents master classes at different institutions including the University of Chicago, Drake University and the Valley Vocal Jazz Summit. 

Allgood has released three albums (both self-published and through Cellar Music), which are available on all streaming platforms. Her most popular song on Spotify, “There Are Such Things,” has over 50,000 streams.

Deitemyer, who has known Allgood for about a decade, said she has the heart of an instrumentalist. 

“There are a lot of singers that prioritize the lyrics or the story of a song, but they’re not necessarily thinking about how it feels musically or how the band feels, you know?” Deitemyer said. “As a drummer, when there’s a singer that can really swing hard and tries to feel and sing like a musician, that’s just so engaging to play with. And Alyssa does that really well.”


Madsen and Allgood celebrate the 1960s American jazz duo of Nancy Wilson and Cannonball Adderley. (Photo Courtesy of Antonia Mufarech)
Chris Madsen and Alyssa Allgood celebrate the 1960s American jazz duo of Nancy Wilson and Cannonball Adderley. (Antonia Mufarech/MEDILL)


 Allgood’s passion for jazz grew stronger as her legs grew taller. While being raised in Westmont, Illinois, she was involved in her elementary school’s music program. When she was in sixth grade, Allgood started singing with the jazz band.

“I did everything: I sang with the jazz band through high school, went to a jazz camp every summer since I was 12 and even did musicals, which is hard to believe because it’s very different to what I do now,” Allgood said. 

As an undergraduate student at North Central College in Naperville, Allgood studied music and sang with several ensembles.

 Throughout this process, Allgood said she always received support – and tunes – from her family and teachers. Other than having parents (and an older brother) who would listen to jazz and blues, Allgood’s mother, a former music therapist, worked at a school for children with autism, teaching them how to process, feel and learn through songs. Although Allgood’s father doesn’t play an instrument, lyrics filled every space of the house. Music was all Allgood heard – and saw – growing up.

 “Back when I was younger and I started singing with the jazz band, from a shallower perspective as a kid, that was a chance I got to sing as a soloist,” she said. “There was something that seemed like a little bit more to it than pop music. I liked the messages I was singing, and I really liked getting to sing with a live band, as I think that in some other genres you could just sing with backing tracks.”

 Allgood tries to give her students at Allgood Jazz Studio the sense of support and community she received growing up because a career in music isn’t the easiest. 

“As a singer, our instrument is who we are. It’s in our body,” Allgood said. “There’s really a level of vulnerability and risk-taking that you must have. So, I think that’s a really beautiful and daring thing that singers do – and my main goal is to help people feel confident that they can use music to express themselves.”

 But other than teaching vulnerability, Allgood embraces it herself, as creating original music involves constant exposure to the public (and therefore room for criticism). To Allgood, sharing herself is beautiful – but totally scary. 

 “As jazz singers, we don’t only have to sing pretty songs about love or heartbreak – those songs are so beautiful, and I still feel love and heartbreak, of course,” she said. “But I think that we can say so much more. And that’s what I’m figuring out: What is it that I want to say? And I think that self-love is something I certainly need a reminder of all the time, and I know that other people do so too. So now, I’m writing those things out – and feeling sort of brave enough to share.”

This year, as she works through her fourth album and aims to seal a deal with a record company, Allgood said she must constantly remind herself to prioritize her own well-being, which she hopes to transmit through her music. 

For now, she will continue teaching, studying, performing original songs and honoring some of her favorite singers, such as Nancy Wilson, like she did on a snowy night at Winter’s Jazz Club.

“People stop and stare, they don’t bother me

For there’s nowhere else on earth that I would rather be …”


Antonia Mufarech is a Magazine graduate student at Medill. You can follow her on Twitter @antomufarech.