Over Labor Day weekend, the Bean hosted a surprise daily ritual. In the late afternoon, tourists gazing at the sculpture would be pulled away from their selfies by the raucous sound of a second-line band. The Windy City Ramblers — led by the bouncy trumpeter Mario Abney and, sometimes, his two pint-sized kids — would then process into Pritzker Pavilion. Throngs would follow them, like jerseyed Pied Pipers. Don’t be shy, the procession seemed to say. This is where you should be.
Welcome to the Chicago Jazz Festival, on locals’ calendars but often a happy discovery for the many holiday-weekend visitors who descend on our city. Those who stuck around Pritzker Pavilion got a primer in jazz and its many strains: its early days, embodied by reedist Natalie Scharf, stride pianist and singer Paul Asaro, and four pairs of swing dancers (Sunday); more New Orleans greatness, via trumpeter Kermit Ruffins and his Barbecue Swingers (Saturday); and otherworldly vocal talent, like operatic countertenor-turned-jazz-singer G. Thomas Allen (Sunday).
On a very autumnal weekend, the festival also transported listeners to the sunny Caribbean. I can think of only one other musician who is as young at heart as Jamaican pianist Monty Alexander, 81: Herbie Hancock, who himself turned 80 this year. Alexander pulled out a baby-blue melodica to lay down a filthy ska rhythm for his band. As he had during 2023’s Ramsey Lewis tribute, Alexander paid homage to fellow countrymen Bob Marley and Harry Belafonte, sneaking in snippets of “Day-O” all set long. Later, he ignited the crowd when he brought out Weather Report drummer Bobby Thomas Jr. as a special guest.
Between Irakere at Ravinia and the Buena Vista Social Club’s Eliades Ochoa as a festival closer, it’s been a great summer for Cuban jazz. Like danceable sendoffs of yesterday, Ochoa brought the audience to its feet for Buena Vista classics like “Chan Chan” and “El Cuarto de Tula.” But he also included a heap of originals from his 2023 album “Guajiro,” starting with “Vamos a alegrar el mundo.” That they did.
If you want to be in Ochoa’s band, you’d better be at the top of your instrumental game and be able to sing. Bassist and singer-songwriter Esperanza Spalding must share that prerequisite. The members of her crack band — multi-instrumentalist Morgan Guerin, drummer Eric Doob, and guitarist Matthew Stevens — backed her voice with lush three-part harmony.
What a voice it is, and has been. Like the rocket-ship earrings she wore on Thursday, Spalding can blast off into the stratosphere, whether for ornamental effect in “Thang (Hips)” or to literally scream, as in her space-age riff on “I Want It Now” from the 1971 “Willie Wonka and the Chocolate Factory.” (And kudos to Spalding for using her last moments on the Chicago Jazz Fest mic to shout out the 60th anniversary of the Association for the Advancement of Creative Musicians — oddly muted in this year’s celebrations, save Pavilion slots for saxophonists Ari Brown and Ernest Dawkins.)
Spalding’s output sounds like music to come. But she foregrounded her skepticism of our screen-happy present in “Dancing the Animal (Mind),” off 2018’s “12 Little Spells. “Have you prayed to your phone today?” asks the central refrain.
Singer-songwriter and pianist Patricia Barber was singing about that same technoskepticism while Spalding was still in high school. “Company,” off her breakthrough 1998 album, got a suave and sophisticated redux on Friday, Barber preparing the Pavilion Steinway to sound like a hollow banjo and Jon Deitemyer holding down the skittering rimshot groove.
No one on the Chicago scene writes music remotely like Barber’s. Who else could reference Hockney, Hopper, Goya and Picasso without eliciting eyerolls (from 2002’s “If I Were Blue”), or “Do you think of me like salt? / Do you taste me in your tears?” (from 2008’s “Snow”)? Or smuggle progressive jazz — those lancelet-sharp lyrics, on a canvas of fuzzed-out guitar and progressive harmony — in lounge-listening sheep’s clothing?
And yet: Barber has not played the Chicago Jazz Festival since 1992, near the very start of her local career. When she did, she said, she was warned by a member of the festival committee not to play any originals.
But on Friday? “I just played a set of all original music,” Barber said, to raucous applause.
Her thoughtful colleagues helped those subtleties sing. Like Barber’s music itself, guitarist Neal Algers subtly bucks expectation, from his harmonic slipperiness to étude-like efficiency in his solo passagework off Santana’s “Black Magic Woman.” And bassist Emma Dayhuff has been a high point of every ensemble I’ve heard her in, urging bandmates and audience alike to think deeper, listen deeper. In her first solo, Dayhuff hushed her sound over the course of the solo; the others onstage followed her. The entire Pavilion seemed lean in, hanging off her every note.
Barber wasn’t the only Chicago regular with a shocking festival snub. Saxophonist Ernest Dawkins, the motor powering the Englewood Jazz Festival—which just tacked on an extra two days to include a coveted Roscoe Mitchell booking on Sept. 16 — made his first festival appearance since 2014 on Saturday. He was flanked by a reboot of his New Horizons band, mostly featuring alumni of his Young Masters program: bassists Ethan Philion and Micah Collier, drummers Isaiah Spencer and Frank Morrison, trumpeters Marquis Hill and Jamal Damien, tenorist Kevin King, and guitarist Senya Rogers-Kaufman. Before kicking off with “Zulu Alchemy,” a Dawkins original, the musicians began by devotionally facing east, easing in with tiny chimes and smoky figurations.
As bandleader-slash-sensei, Dawkins’ leadership was relaxed — at times perhaps too relaxed, his young, alert colleagues scrambling to keep up with several surprises. Or was it intentional, one more smirking test of mettle by their longtime mentor?
Either way, the young guns blazed through the trials. King commanding the stage with inventive conflagrations, fleet unison fingerwork by Collier and Philion, Rogers-Kaufman offering solos both cerebral and thrilling, and Damien winging through long features with the agility of a sparrow.
Some of Barber and Dawkins’ standout sidemen got their own spotlights on Sunday: King with his shredding Kevin King Regime trio (also behind one of the most gripping local releases of the year, “Call to Action!”), Algers with a smoothly coasting quintet set, and Morrison with his FM trio, also including Collier on bass.
Another musician who didn’t ask for your attention but demanded it: Maddie Vogler, bopping around the festival on Saturday as both a bandleader and ensemble member. The young alto player convened a sextet of young powerhouses at the WDCB stage before linking up with trumpeter Victor Garcia’s septet at the Von Freeman stage later in the afternoon. There, her features flashed with high-beam brilliance, whether sitting in the solo hot seat or interlacing with Garcia in a duet.
Even younger talent to keep an eye on? The student musicians invited to play at the Harris Theater Rooftop stage. Every year, the festival invites groups from the region’s top jazz programs. This summer, I caught a big band from Whitney Young, the hyper-selective magnet school in West Loop. Among the featured performers were trumpeter Silas Moody, off to Stanford University later this month; Titobi “Tito” Olusanya, a freshman whose tenor sound is already the envy of much more experienced players, and Raffaella “Raffi” Lawson, a bubbly 16-year-old guitarist who also outed herself as a precocious contralto when she stepped up to sing Ella Fitzgerald’s “I Like the Sunrise.”
All three were swarmed by adoring fans after the set. But Olusanya — deep-voiced, serious and already dead-set on pursuing a music career — told me that the main thing on his mind, post-performance, was how to get even better.
“I think I can say that I did a decent job trying to incorporate everything I wanted to,” he says. “But it’s a challenging piece that I think that I could still work on.”
Spoken like a true musician.
Hannah Edgar is a freelance critic.
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