Alyssa Allgood/Photo: Adrien H. Tillmann
In the glory days of jazz and big bands, a singer who could scat, bend notes, jump octaves and interpret lyrics would have been placed before a band, given arrangements and a microphone and told to sing. Alyssa Allgood can certainly scat, bend notes, jump octaves and interpret lyrics. But in a sign of a changing world, she also composes music, arranges compositions and often chooses the songs that she performs.
Allgood has also performed at such notable venues as Jazz at Lincoln Center’s Dizzy’s Club, Blues Alley and the Birdland Jazz Club. In Chicago, she’s a regular performer at both the Green Mill and Winter’s Jazz Club. She was heralded as a Rising Star Female Vocalist in the 2024 and 2025 “Downbeat Magazine Critics Poll,” and won the inaugural Ella Fitzgerald Jazz Voice Competition.
But in today’s narrowing jazz marketplace, added skills and talents can make the difference between a career and a hobby. Creating a musical vision—penciling in staves and half notes on scores and lead sheets—has been another venue that has vaulted her career. Allgood’s compositions were selected as finalists in the jazz category at the 2023 John Lennon Songwriting Contest, and in the International Songwriting Competition that same year. While there are, of course, many composers and instrumentalists who write their own music, the list of singer-composers in the field of jazz is much shorter.
“Even though I am a vocalist, I have always been drawn to the instrumental side of jazz,” Allgood says. “I wanted to experience that music not only as a vocalist, but to see it from the point of view of the person on the bandstand. So for me,” Allgood continues, “that turned into being able to write and arrange my own music, and present something that is very much my own thing.”
A native of Westmont, Illinois, Allgood was encouraged to pursue music by her mother, who was a music therapist, and her father, who loved blues. Her interest in jazz began at the age of twelve, when she attended a vocal jazz camp and started singing in a jazz choir in the sixth grade.
“At that time, there were a lot of things going on like Norah Jones’ ‘Don’t Know Why,'” Allgood says. “Then I was singing ‘Skylark’ and a lot of beautiful songs, which gave me a sort of formative experience. As time went on I discovered there was, at least for me, a greater musical and emotional depth in jazz. Then there is improvising which, even at a young age, I found exciting—that I could sing something that would never be the same again.”
Like many jazz singers, Allgood began singing the Great American Songbook, featuring songs by tunesmiths like Cole Porter, Richard Rodgers and Lorenz Hart. Her compositions strayed from these standards, and Allgood initially questioned whether her songs could combine her own individual expressions and still fit into the genre. Not to mention the question all artists of any kind ask themselves: “Am I really good enough?”
Alyssa Allgood/Photo: Dominic Guanzon
This question was perfectly asked and answered in the first cut on Allgood’s new, appropriately named EP, “Leap.” Although she possesses a master’s in music and jazz studies from DePaul University, Allgood’s use of simile and her ability to turn introspection into verse express the keen pen of a poet.
The song begins softly, with lyrics like, “Safely building on dry land, she can hear the ocean’s song… but she’s afraid to sing along.”
Yet as the tempo rises, Allgood expresses her own found confidence, singing “If not now, then when… leap into the sea, can’t you see that you belong in the sea.”
This theme continues with her composition, “Little Bird, Fly,” which relies on a more common metaphor for freedom, as does the song “In My Way.” Like the old Supremes/Vanilla Fudge song, “You Keep Me Hangin’ On,” it speaks to how people can be held back. Instead of a gaslighting partner, it is Allgood’s bonds of inner self-doubt that need to be broken.
Allgood also displays her arranging skills on the new EP. In covers of standards like “I’m Old Fashioned” and “Devil May Care,” changing time sequences blend with interspersing piano fills by Julius Tucker, brief but powerful, and the soaring trumpet and flugelhorn of Victor Garcia.
On vocals, Allgood possesses the power to punch through the ceiling on choruses and taglines, turning heads and opening eyes. On “Devil May Care,” she scats for almost the entire length of the song. First, small, short bursts of notes dart in and out like a mouse in a maze. Then Allgood’s vocals begin to reach higher, beeping, bopping—still in 1/16 time, but speaking jazz. Bit, bop, du-wop; small, fast, then rising higher; scaling one, two octaves while holding the same note, then dipping down again like a shooting star darting. Then disappearing across the sky.
“When I grew up going to that camp, I was so afraid, but over the years I have studied and studied, transcribing from instrumentalists, and those transcriptions force you to develop your range because they are playing in higher notes,” says Allgood, who also teaches jazz vocals at Loyola University. “I also studied classical music, which allowed me to reach a higher register, which I use mostly when I am improvising. I have also been so influenced by the great female vocalists. Right now in my office, I am looking at a picture of the great Sarah Vaughan, who could sing three octaves in a two-measure frame. These artists had complete freedom and also control of their instrument. That is my ultimate goal—one that I will continue to strive for.”
As the former winner of the John Lennon Songwriting Contest, Alyssa Allgood will be celebrating the music of Lennon and McCartney at Winter’s Jazz Club on March 1.
“Mad-Good—Salutes the Beatles: Celebrating the Songwriting of John Lennon & Paul McCartney” is at Winter’s Jazz Club, 465 North McClurg Court, on March 1. Sets at 5:30pm and 7:30pm. Tickets are $30-$35, available at wintersjazzclub.com.
