Wander into Otto’s Restaurant & Bar on Madison’s west side any summer Wednesday between 5:30 and 7:30 p.m. and you will hear the dulcet tones of jazz singer Gerri DiMaggio and her trio performing on the restaurant’s outdoor terrace.
The night we visited, the four musicians — which included DiMaggio’s husband Bob Pesselman on guitar, Paul Hastil on keyboards, and John Mesoloras on bass — had just finished Chet Baker’s “Let’s Get Lost” and were launching into a surprisingly mellow version of Dizzy Gillespie’s “A Night in Tunisia.” Other standards from Wes Montgomery, Duke Ellington, Charlie Parker and Dinah Washington would soon follow.
DiMaggio fronted the band, adding light percussion to the mix and building a bridge between the musicians and the 20 or so diners on the terrace with her mellifluous alto. After 18 years of playing Otto’s, there was nothing routine about Dimaggio’s performance — she demonstrates formidable talent and enthusiasm.
“I am a vocalist drawn to storytelling,” says DiMaggio. “Singers can perform the same song, but each of us does so differently, using different phrasing or playing off the melody in a different way. To me, jazz is simply poetry.”
A Madison native, DiMaggio considers herself lucky to have been born into a musical household, with a mother who played the music of Tony Bennett, Billy Eckstine and others. But it was an impromptu concert by fellow Madisonian Tracy Nelson, who went on to form the band Mother Earth, that helped DiMaggio find her calling.
“Tracy showed up for seventh period at the old Madison Central High School with her guitar and started playing and singing folk music,” says DiMaggio, who was a student at the time. “I thought, ‘That’s what I want to do when I grow up.’”
When she was 19, DiMaggio’s path veered to Aspen, Colorado, where she lived the life of a ski bum, singing country blues and managing a specialty store in nearby Snowmass. Thanks to new friends from New Orleans and Aspen’s sophisticated music scene, DiMaggio’s appetite for jazz kept growing. When she returned to Madison, she nurtured that passion by studying music and vocal performance at UW-Madison with renowned jazz bassist Richard Davis.
She opened DiMaggio’s Euro Design, which sold upscale home furnishings, and pursued her jazz career at night.
“I operated the store for 25 years and it was a great experience,” she says. “I do a lot of booking for the band and the business experience helped.”
She closed the store in 2010 to concentrate on her music, diving in to further study famous female jazz vocalists, including Billie Holiday.
“Billie was a very delicate singer, and I was blown away by her,” DiMaggio says. “My records are almost worn out because of how much I played them.
“I like a lot of sad songs, and that’s why I am drawn to Billie Holiday, who had a sadness and quiet emotion in her singing. I don’t have a big voice and I need to take a more subtle approach to music.
“Carmen McRae, on the other hand, had a tougher, more intense vocal approach,” she adds. “Sarah Vaughan had amazing skills, and Ella Fitzgerald was upbeat, light, bright and could sail on a song. They got me started on the road to jazz.”
DiMaggio is also greatly influenced by Brazilian music, including vocalist Flora Purim, who performed with jazz-fusion artists Chick Corea and Stanley Clarke.
“Miles Davis’ favorite singer was Shirley Horn, who had a very subtle approach,” she adds. “It’s a lot about how you deal with space and time in musical performance that determines your approach as a singer. As I’ve progressed in my musical career, I’ve come to better understand those principles.”
DiMaggio strives always to connect — as a songwriter and interpreter — with her appreciative audiences. “My music is a reflection of how I look at my life,” DiMaggio says. “Music centers you. You have to be in the moment as you go from one phrase to the next. It’s very meditative.”
Gerri DiMaggio World Jazz Unit will perform at the Memorial Union Terrace on Aug. 2 from 5-7 pm.
