Sabrina Carpenter is joined by Earth, Wind & Fire while performing at the T-Mobile stage on the last day of Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
Our pool of genuinely funny music performers has never been large. Musicians get timid about humor, with reason. Audiences take earnest artists seriously and let time and taste catch up to anyone who takes their own importance with a grain of salt. That’s one of the reasons why Sabrina Carpenter played so exuberantly in Grant Park on Sunday night. She closed Lollapalooza with real effervescent wit, even joy. Imagine! Looking goofy on stage! We had the introspection of Tyler, The Creator; the gated-community angst of Gracie Abrams; and the sunny rebellion of Olivia Rodrigo.
But god, Sabrina Carpenter is fun.
Her stage, festooned with a huge curling “SC” traced in stage lights, not only paid homage to Chicago as the original home of “Soul Train,” she and her dancers threw in their own version of a “Soul Train” line dance. By the end of the first song, she was in a conga line. Within a few songs, she’d settled into a sort of samba twang for “Slim Pickins,” with its great chorus: “Since the good ones are deceased or taken / I’ll just keep on moanin’ and bitchin.’”
Midway through, nodding to Chicago cool again, she brought out Earth, Wind & Fire, along with its entire horn section, for an inspired bop through “Let’s Groove” and “September.”
I was not expecting chills in August, yet here we are.
Carpenter — whose act fits nicely into the contemporary wave of ubiquitous young woman pop singers, though works subversively, even subtly, against the mold — loaded her set with the winks, bumps, put-downs and self-deprecations that dance across her albums. She’s such a knowing throwback to ‘70s variety shows that her stage even mimicked TV studios, bundling the stage cameras into the kind of large swiveling stands associated with the days of live TV. In another life, Carpenter could have been Carol Burnett. Or Carole Lombard. Or maybe a Looney Tunes rabbit. But definitely a character.
Sabrina Carpenter, at least on stage, her Lolla set confirmed, is a role, albeit with a heart. You could argue that of Rodrigo, Abrams, Taylor Swift, Chappell Roan, Charlie XCX, the wave of woman superstars that get lumped colloquially as “the pop girlies.” But among this group, the Super Friends of Pop, only Carpenter reminds you she is a confection. A former Disney Channel star (of course), her playful nods to showbiz convention and cliche feel second nature — not unlike the way, say, Martin Short feels born to the stage. When she closed with the inevitable “Espresso” — last year’s song of the summer — and its nonsensical “That morning coffee, I brewed for ya / one touch and I brand-newed it for ya,” a teenager beside me, singing, threw in the song’s quiet aside:
“Stupid.”
It’s there, in the studio version of “Expresso,” a sardonic meta-quip from Carpenter about own writing, which can get so tangled in heated knots, it’s just shy of camp in places, only to turn clever again. This might be Carpenter’s finest quality, her ability to surprise without underlining any effort. At the lip of the stage, accompanied by an acoustic guitar, she managed to be intimate despite playing to the population of a small city: “I know you’re not the sharpest tool in the shed,” then plainly added: “We had sex, I met your best friends.” Her knack for detail met noir-laced burlesque in “because i liked a boy,” which opens, “I said I wanted Thin Mints and you said you knew a guy,” only to rage, “Now I’’m a homewrecker, I’m a (expletive) / I got death threats filling up semi-trucks.”
A beat later, she’s working those Groucho Marx eyebrows, singing: “Where art thou? / Why not uponeth me?”
Carpenter is camp the way that Dolly Parton is camp, fully in charge of the tone without sacrificing brains. You take her seriously because she’s funny, and shrewdly provocative. On her previous tour, she sang a song while seated on a toilet seat, which — and this is the best part — she would wipe down before she sat.
For Lolla, she framed the show as “SC News Chicago,” incorporating satiric commercials between songs, a parody of 1-900 chat line ads for “Bed Chem,” a commercial for “Manchild Spray” before her recent hit, “Manchild,” the song of this summer: “And how survive the Earth so long? / If I’m not there, it won’t get done / I choose to blame your mom.” The men in her songs are basically Wile E. Coyote, and she is the Roadrunner, addicted to the chase. She’s not above declaring herself horny.
But then going broad works at Lollapalooza.
A$AP Rocky performs at the Bud Light stage during Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
A$AP Rocky performs at the Bud Light stage during Lollapalooza in Chicago’s Butler Field, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
Sabrina Carpenter performs at the T-Mobile stage before a large crowd during Lollapalooza in Chicago's Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
A crowd member sings along to A$AP Rocky’s performance at the Bud Light stage during Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
Sabrina Carpenter performs with Earth, Wind & Fire perform at the T-Mobile stage during Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
María Zardoy, lead singer of The Marias, performs at the Bud Light stage during Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
People cheer for The Marias during their performance at Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
María Zardoy, lead singer of The Marias, performs at the Bud Light stage during Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
Finneas performs at the Lakeshore stage during Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
Finneas performs at the Lakeshore stage during Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
A shark mascot dances in front of a crowd during Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
Estefano Libelli, of Florida, helps Maisy McDermott, of Massachusetts, with her cowboy boot during Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
Kaia Pierce, of Lakeview, dances while Rebecca Black performs at Perry’s stage during Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
Rebecca Black performs at Perry’s stage during Lollapalooza in Chicago’s Grant Park Sunday, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
Rüfüs Du Sol performs on the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Rüfüs Du Sol performs on the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
People dance as Rüfüs Du Sol performs on the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Rüfüs Du Sol performs on the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Rüfüs Du Sol performs on the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Rüfüs Du Sol performs on the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Doechii performs on the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Doechii performs on the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Doechii performs on the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
A fan cries as Doechii performs on the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Doechii performs on the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Chance the Rapper performs on the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Chance the Rapper performs during the third day of Lollapalooza at Grant Park on Saturday, Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Daisy Cervantes cheers for Ca7riel and Paco Amoroso during the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
From left, Taylor Fruetel, Avery Ranshau and Joy Vanlaarhoven, smile for their friends in matching outfits during the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Arturo Trevino, center, dances as Chance the Rapper performs during the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Liam Goyal, left, and Shalin Desai eat nachos during the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Victoria Gonzalez, 8, of St. Louis, Mo., smiles among bubbles during the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
People dance to Layz during the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
People jump and dance to Layz during the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
People dance to Layz during the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Jackie Garland, holds her daughter, Goldie Garland, 1, while listening to Daniel Allan during the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Zaineb Bahrainwala, left, and Haleema Gurmani show their accessories during the third day of Lollapalooza at Grant Park on Saturday, Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
The Winnetka Bowling League following their performance during the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Jasmine Louie dances to Ca7riel and Paco Amoroso during the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Thousands attend the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Thousands attend the third day of Lollapalooza at Grant Park on Aug. 2, 2025. (Audrey Richardson/for the baiduhai)
Olivia Rodrigo performs at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Festival attendees sing along as Olivia Rodrigo performs at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Olivia Rodrigo plays guitar while performing at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
The setting sun illuminates festival attendees at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
T-Pain, center, performs at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Festival attendees watch T-Pain perform at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Amaarae performs at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Festival attendees watch Amaarae perform at Lollapalooza , Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
A festival attendee holds a Mandalorian helmet and a can of beer while watching Foster the People perform at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Star Bandz performs at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
A festival attendee holds a drink cup with her teeth to use both hands for her phone camera while watching Star Bandz perform at Lollapalooza Friday, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Star Bandz performs at Lollapalooza Friday, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Festival attendees take pictures in front of an inflatable Lollapalooza sign, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Festival attendees walk on South Columbus Drive at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Daniel Oberman, left, and Samantha Arellano dance as Isabel LaRosa performs on the Lakeshore stage during Lollapalooza in Grant Park on Aug. 1, 2025. (Eileen T. Meslar/baiduhai)
Gigi Perez performs on the T-Mobile stage during Lollapalooza in Grant Park on Aug. 1, 2025. (Eileen T. Meslar/baiduhai)
Festival attendees take pictures in front of a mirror installation at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Festival attendees dressed dressed as corn watch a deejay performance at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Festival attendees dressed in rainbow-themed outfits watch a deejay performance at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Isabel LaRosa performs on the Lakeshore stage during Lollapalooza in Grant Park on Friday, Aug. 1, 2025. (Eileen T. Meslar/baiduhai)
Festival attendees receive free hair styling touchups at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Chicago police officers in a helicopter survey the grounds above Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
A festival attendee holds a film camera strap with her teeth while walking on South Columbus Drive at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Festival attendees take pictures with an inflatable mascot at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Festival attendees walk from one stage to another at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
A festival attendee dances to music from a nearby stage while walking at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Festival attendees rest under tree shade near food vendors at Lollapalooza, Aug. 1, 2025, in Chicago. (John J. Kim/baiduhai)
Fans sing along to Luke Combs’ performance at the Bud Light stage at Lollapalooza in Chicago’s Grant Park on July 31, 2025. (Dominic Di Palermo/baiduhai)
Luke Combs performs at the Bud Light stage at Lollapalooza in Chicago’s Butler Field Thursday, July 31, 2025. (Dominic Di Palermo/baiduhai)
Luke Combs shotguns a beer while performing at the Bud Light stage at Lollapalooza in Chicago’s Grant Park on July 31, 2025. (Dominic Di Palermo/baiduhai)
Cage the Elephant guitarist Brad Shultz performs at the Bud Light stage at Lollapalooza in Chicago’s Grant Park on July 31, 2025. (Dominic Di Palermo/baiduhai)
A crowd listens to Tyler the Creator’s performance at the T-Mobile stage at Lollapalooza in Chicago’s Grant Park on July 31, 2025. (Dominic Di Palermo/baiduhai)
Gracie Abrams performs for a packed T-Mobile audience on the first day of Lollapalooza in Grant Park in Chicago on July 31, 2025.
(Dominic Di Palermo/baiduhai)
Cage the Elephant lead singer Matt Shultz performs at the Bud Light stage at Lollapalooza in Chicago’s Grant Park on July 31, 2025. (Dominic Di Palermo/baiduhai)
Dylan Carney of Batavia and Andrew Hager of Elburn relax on the grass while Sierra Ferrell performed at the Bud Light stage during Lollapalooza in Chicago’s Grant Park on July 31, 2025. (Dominic Di Palermo/baiduhai)
Cage the Elephant lead singer Matt Shultz performs at the Bud Light stage at Lollapalooza in Chicago’s Butler Field Thursday, July 31, 2025. (Dominic Di Palermo/baiduhai)
From left: Jennifer Puente, Lindsey Puente, and Janine Alaniz, all of Texas, take a selfie at Lollapalooza in Chicago’s Grant Park Thursday, July 31, 2025. (Dominic Di Palermo/baiduhai)
Kenzie Shultz, of Girl Tones, performs on the BMI stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
People dance while Azzecca performs at Perry’s stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
Dominick Hernandez dances as The Blessed Madonna performs on the Perry’s stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
Azzecca performs at Perry’s stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
Alexis Felt uses a bubble gun while Azzecca performs at Perry’s stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
People dance to Azzecca at Perry’s stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
Kenzie Shultz, of Girl Tones, performs on the BMI stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
Macy Liddy dances as The Blessed Madonna performs on the Perry’s stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
Kenzie Shultz, of Girl Tones, performs on the BMI stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
Rachel Town, left, and Allison Ruff dance to Ratboys at the Bud Light stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
Laila Crowe, of Girl Tones, performs on the BMI stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
Julia Steiner, of Ratboys, performs at the Bud Light stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
Julia Steiner, of Ratboys, performs at the Bud Light stage during Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
Air pollution shrouds the skyline while people attend Lollapalooza in Grant Park on July 31, 2025. (Eileen T. Meslar/baiduhai)
Music fans are let into Grant Park on opening day of Lollapalooza, July 31, 2025. (Eileen T. Meslar/baiduhai)
Attendees wait in line to be let into Grant Park on opening day of Lollapalooza, July 31, 2025. (Eileen T. Meslar/baiduhai)
People walk with suitcases outside the Congress Plaza hotel before the first day of Lollapalooza Wednesday July 30, 2025, in Chicago. (Armando L. Sanchez/baiduhai)
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A$AP Rocky performs at the Bud Light stage during Lollapalooza in Chicago’s Grant Park, Aug. 3, 2025. (Dominic Di Palermo/baiduhai)
In fact, it may be the only way to perform here now — if only because Grant Park becomes so overcrowded during headliners like Carpenter that unless you’re up front somewhere near the stage, you’re watching this on screens the entire time or you’ll have to wait for a clip on TikTok or Instagram to spot anything sly or understated. Once again, Carpenter understands the assignment. She asks “It’s 10 p.m., do you know where your girlfriend is?” then moments later notes how “grateful” she is. She sends-up the corny tropes of a generation of hitmakers with a comforting bit of heart. She’s all off balance, sincere but sincerely silly. She looked out on Lollapalooza Sunday — which, by day four, is basically “Lord of the Flies” — surveyed the mess and laughed.