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“Are you ready to hear the story of my life?” When the person asking that question is Madonna, you don’t dare answer in the negative. Especially when the storytelling involves decades of groundbreaking pop, a squadron of talented dancers and a seven-act presentation that doubles as fashion week on steroids.

Performing Thursday at the first of a two-night stand at the United Center, the cultural icon revealed another side of herself we’ve never fully seen: Madonna as an artist looking back. Primarily leaving the politics, psychoanalysis and aspirational theater of prior outings behind, the 65-year-old singer known for staring ahead entertained the pull of nostalgia for the first time on a tour.

Though nearly all of her generational contemporaries slipped into the equivalent of Las Vegas mode long ago, Madonna fought to remain modern and relevant — and stay on the cutting edge. As should be expected of the aptly named Celebration Tour, the vocalist’s idea of reflecting on her own history went far beyond a standard greatest-hits program.

Ambitious, sexy, inclusive, buoyant, vibrant, defiant and, on occasion, messy, awkward, and overly busy: The 135-minute spectacle mirrored the very traits that define Madonna’s career. On a larger scale, it underlined how her immeasurable influence transcends music and carries over to style, sexuality, imagery, free speech, feminism and the LGBTQ community.

Announced in January 2023 via a star-studded promo, the trek hasn’t entirely gone as planned. The initial North American dates — including two shows here last August — were postponed after the singer suffered a near-death health scare in late June. After being discovered unconscious in her home by her Kabbalah teacher, Madonna spent several days hospitalized in intensive care and underwent an induced coma to treat a severe bacterial infection. The re-routed trek kicked off in mid-October in London and debuted in the States in mid-December.

At opening night at Barclays Center in Brooklyn, New York, Madonna hit the stage more than two hours past the posted start time. Longtime followers won’t find the tardiness surprising; the singer has a reputation for forcing audiences to endure long waits. (She went on right before 10 p.m. in Chicago on Thursday and finished shortly after midnight.) Though most fans turn to social media to vent frustrations, two New York ticketholders took their grievances to a new level by filing a class-action lawsuit alleging “unconscionable, unfair, and/or deceptive trade practices” as well as “a wanton exercise in false advertising.”

Madonna and her tour promoter, Live Nation, pledge to vigorously defend themselves against the accusations. Besides, this isn’t Madonna’s first rodeo with such legal threats. A pair of similar lawsuits connected to her 2019 Madame X Tour were voluntarily dismissed.

Did these challengers happen to forget who they’re targeting? “Bitch, I’m Madonna” she triumphantly declared Thursday as members of her ensemble marched about wearing recreations of vintage costumes forever tied to the singer: material girl, bride, Egyptian goddess, spy, athlete, wild child, gypsy and haute-couture model among them.

Working in conjunction with the personality-positive message and mindless fun of the electronic-based song, the visual parade stood as one of the show’s savviest moves — and made far more sense than the bizarre appearances by a masked mannequin-like character that, per the vocalist, allegedly represented a doppelganger of a 20-something Madonna.

Keeping tabs on the real Madonna often proved enough of a challenge. She soared above the crowd in a mobile “time machine” that resembled an illuminated elevator car; camouflaged herself with black veils and thick robes; perched behind drop-down video screens; and ascended and descended through trap doors located in an extensive network of runways. Six interludes provided her brief opportunities to disappear and allow her cast to take charge. Kudos to Bob the Drag Queen for embracing the role of hype diva with charm and panache.

Madonna attempted to strike her own balances between joyful and sorrowful, humorous and serious, extroverted and intimate, simple and complex. Several aims missed their mark. Though short, the handful of transitional skits seemed stiff and amateurish. The bigger mistake related to the decision to use pre-recorded backing tracks rather than a live band. Though it allowed Madonna to blur the lines between actual singing, Auto-Tune assistance and potential lip synching, the sound was thin and synthetic. Imagine listening to Madonna on a twin-cassette boombox — likely not the intended effect, but given the retro flair, somewhat ironic.

The singer’s choreographed interactions with ensemble personnel during songs felt more natural, substantive and meaningful. A dark reading of “Like a Prayer” witnessed the vocalist engage with masked, topless dancers hanging from a revolving carousel that looked like a giant wheel rim turned on its side. “Erotica” placed Madonna with glitter-gloved pugilists and around boxing rings roped off with light beams. The cast let loose on “Vogue,” which peaked with a dance contest, lighthearted judging and simulated sex acts. For “Open Your Heart,” the superstar expanded on the risque dancing and chair prop tied to the original video for the 1986 hit.

Subtle and obvious, references to signature Madonna iconography and moments peppered the set. She paid homage to her Blond Ambition Tour and its controversies with a replica of the famous velvet bed and the presence of a woman who channeled 1990 Madonna down to the gold outfit and ponytail. Remember the three-layer wedding cake from her pioneering 1984 appearance on the MTV Video Music Awards? It informed the triple-tier stage and its turntable platform. A salute to Michael Jackson also connected to that period.

Ditto a montage of video and audio clips that highlighted the countless barriers Madonna tore down since emerging as a public figure. Just as the innocuous beats of the disco-etched “Everybody” and bounding “Into the Groove” harkened back to an more buttoned-down era guided by conservative taboos, so did flashing news reports and tabloid headlines that hinted at the extent to which Madonna helped change social mores and empower disenfranchised groups — and how many forms of expression, behaviors, attitudes and communities are now more widely accepted. A somber “Live to Tell,” augmented with banners and pictures of important figures who died from AIDS, emphasized the awakening transformations that have occurred.

Of course, championing the past tends to acknowledge certain truths about the present. Madonna covered decades of work but almost exclusively focused on the ’80s and ’90s. She played just two songs from her last five albums, which stretch back to 2005.

To her credit, none of the selections came across as forced, artificial or dated. She drew on country, reggaeton, R&B, EDM, new wave, classical and more. Several songs received infusions via club remix updates. And she ran out of room to accommodate everything. A truckload of smashes — “True Blue,” “Papa Don’t Preach,” “Like a Virgin,” “Lucky Star,” “Borderline,” “Material Girl,” “Dress You Up,” “Music” — were not included in her setlist.

Thankfully, Madonna’s second single, released in March ‘83, “Burning Up,” made the cut. Strumming an overdriven electric guitar after guzzling from a Budweiser bottle, she dug into the gritty, punk-leaning ethos that always lurked in the song’s background and reframed it as a trashy rock ‘n’ roll number. The vocalist struck a similarly direct chord with “Express Yourself,” radically revamped via a stripped-down arrangement underpinned by Madonna’s acoustic guitar. A collaboration with her daughter, pianist Mercy James, on the ballad “Bad Girl” also moved the needle in ways that escape large-scale productions.

Modesty isn’t usually the leading compliment that springs to mind with Madonna. Yet, for all the flaws, she seemed genuinely grateful, surprised even, to still be alive and able to fill a huge arena on back-to-back evenings at this juncture in her career. Whether the throwback show stands as a self-knowing recognition of achievements, apology for previous offenses, memo to younger peers, victory-lap farewell, trip down memory lane — or combination of any of those possibilities — one certainty persists. Madonna did it her way.

Bob Gendron is a freelance critic.

Setlist from the United Center Feb. 1:
“Nothing Really Matters”
“Everybody”
“Into the Groove”
“Burning Up”
“Open Your Heart”
“Holiday”
“Live to Tell”
“Like a Prayer”
“Erotica”
“Justify My Love”
“Hung Up”
“Bad Girl”
“Vogue”
“Human Nature”
“Crazy for You”
“Die Another Day”
“Don’t Tell Me”
“Mother and Father”
“Express Yourself”
“La Isla Bonita” / “Don’t Cry for Me Argentina” (Andrew Lloyd Webber-Tim Rice cover)
“Bedtime Story”
“Ray of Light”
“Rain”
“Bitch I’m Madonna”
“Celebration”