If Charli xcx’s headlining set was a moody arthouse film, fellow Brit Olivia Dean’s Lollapalooza moment was the feel-good classic you screen on a cozy rainy day — except on Saturday, fans waded in a Grant Park swamp to sing, get emotional and share space with the beloved crooner.
The night was Dean’s first headlining a festival in the U.S., an occasion she welcomed with soul-baring singalongs, bits of wisdom and candor between songs, and a fireworks show that brought a level of connectedness to a mud-covered crowd.
She reflected on having first played Lollapalooza two years ago, telling fans she’d been in tears all day processing her place as Saturday’s headliner.
“To be headlining this year is just crazy and truthfully I’ve been crying all day because I feel so privileged to do this,” Dean confided to the massive crowd that blanketed the field in front of the T-Mobile stage.
The London native’s bright smile and honeyed, slightly raspy, pitch-perfect vocals felt like a balm at the end of a rainy, chilly day. She glided across the main stage in two different silver dresses as her voice floated over her immaculate seven-piece band, rounded out by a horn section and two angelic background singers. Bordering the platforms on the stage were large petals, with Dean often at the center, like a bright blossom.
It has been a whirlwind year for Dean, 27, since releasing her sophomore album, “The Art of Loving,” last September. The record “changed her life,” she said, sending her career on a nonstop upward trajectory, with viral fame, No. 1 singles and a Grammy Award for Best New Artist.
Among those accolades is achieving the longest-running United Kingdom No. 1 single in history with Sam Fender, thanks to their “Rein Me In” collaboration, which has reportedly spent a whopping 19 weeks at the top. For the show’s penultimate song, she brought Fender onstage to perform the folk-rock megahit, their voices melding smoothly as he plucked away on a Jazzmaster.
The song was part of a 19-track setlist of nostalgic R&B, pop and soul devoted to the act of opening oneself up to love and all of the joys, pains and lessons learned along the way.
An early set highlight came when Dean and her background singers layered flawless harmonies for “Lady Lady,” her singers keeping time with shakers, adding texture to an already well-rounded full-band sound.
Just about every song came with an introduction from Dean, who would share its meaning or root. “The Art of Loving” was inspired by reading bell hooks’ “All About Love,” she said.
“The truest way to really love someone in your life is to want them to be the best version of themselves,” she explained, paraphrasing hooks. “Everyone here deserves to be loved that way, and I deserve that too.”
On “Let Alone the One You Love,” she sang a scorned lover’s waltz while the audience rocked back and forth, many with eyes closed and brows furrowed with feeling. “Who would do that to a friend? Let alone the one you love?” she sang, face pained, arms open.
Dean’s live band Saturday also breathed new life into the singer’s earlier material, including “Ladies Room” and “Carmen,” from her 2023 debut “Messy.” Dean said the latter ballad was about her grandmother, who immigrated to the U.K. from Guyana at just 18. Dean declared the song a celebration of her grandmother’s life and dedicated it to all grandmothers and immigrants.
“I don’t understand why we’ve all become so fearful of each other — we’re all just people,” she said before her grandmother’s voice played over the speakers to start the song, recounting her journey.
Another standout moment came during her performance of “A Couple of Minutes,” during which her band interpolated chords from the underrated 1970s soul gem “We Had True Love” by Hot Chocolate. Asking if anyone had been through a breakup recently, Dean said the song is about forgiveness, acceptance and remembering that “just because something didn’t last forever that doesn’t mean it was a waste of your time … anytime you get to fall in love, that was time well spent.”
“F— my ex!” one crowdgoer yelled to a friend before belting out the song’s chorus with seemingly everyone else in the crowd.
Dean fortified the night’s ’70s soul connections with a cover of Curtis Mayfield’s masterpiece “Move on Up” — a bold move in the legend’s hometown. But Dean stuck the landing, also using the song to introduce her band while she jumped and twirled in the reflective light of a disco ball spinning from above the stage.
It all led up to the night’s closer, “Man I Need.” Dean leapt exuberantly as she sang, sending the fringes of her sparkling dress swaying. Amplified by additional horn arrangements and a singalong, the number was a kind of joyful denouement after a set’s worth of emotions.
As fireworks burst above, fans lifted their voices in what felt like the cathartic ending scene of a feel-good rom-com. Dean’s words, from earlier in the night, suddenly clicked in: “If you take anything from this show, it’s go and give the love you feel you deserve.”
Set list
Nice to Each Other
Lady Lady
So Easy (To Fall in Love)
Close Up
Let Alone the One You Love
Messy
Carmen
Echo
Time
A Couple Minutes
The Hardest Part
Baby Steps
Ladies Room
Move on Up (Curtis Mayfield cover)
OK Love You Bye
It Isn’t Perfect But It Might Be
Dive
Rein Me In (with Sam Fender)
Man I Need