Olivia Dean turned her Lollapalooza debut into one of the festival’s most heartfelt moments on Saturday night (Aug. 1), headlining Chicago’s T-Mobile Stage with an emotionally rich performance that blended soulful vocals, intimate storytelling and festival-sized singalongs. Despite rainy conditions across Grant Park, the British singer-songwriter drew a massive crowd.
Opening with the shimmering “Nice To Each Other,” Dean immediately established the warm atmosphere that defined the set. Her performance leaned heavily on 2025’s acclaimed sophomore album The Art of Loving, featuring songs including “Lady Lady,” “So Easy (To Fall In Love),” “Close Up,” and “Let Alone The One You Love.” Earlier favorites such as “Messy,” “Dive,” “Ladies Room,” “Carmen,” and “The Hardest Part” were woven seamlessly throughout the evening.
Between songs, Olivia Dean repeatedly reflected on how dramatically her career has changed over the past year. Addressing the crowd, she shared an emotional message about the album that has defined her latest chapter.
“This album, The Art of Loving, completely changed my life. It’s been a healing process for me, and I’m so proud of it as a body of work. I’m also incredibly proud of this tour, of everything we’ve experienced and the way we’ve managed to connect with so many people. It’s been a truly amazing experience.”
Earlier in the night, she also revealed she had been crying throughout the day while thinking about the journey from performing for roughly 1,500 people in Chicago just a year earlier to now headlining one of the city’s biggest festivals.
The performance reached another high point when Dean welcomed Sam Fender to the stage for their chart-topping collaboration “Rein Me In” before Dean closed with the anthemic “Man I Need.”
Olivia Dean arrived at Lollapalooza during the North American leg of her sold-out The Art of Loving Live Tour, supporting the album released in September 2025. Since then, she has collected the 2026 Grammy Award for Best New Artist while continuing her rapid ascent with hits including “Man I Need,” “Nice To Each Other,” and “Rein Me In.”
Olivia Dean Lollapalooza 2026 Setlist
Nice To Each Other
The Art of Loving (2025)
Lady Lady
The Art of Loving (2025)
So Easy (To Fall In Love)
The Art of Loving (2025)
Close Up
The Art of Loving (2025)
Let Alone The One You Love
The Art of Loving (2025)
Messy
Messy (2023)
Carmen
Messy (2023)
Echo
What Am I Gonna Do On Sundays? EP (2020)
Time
(2024)
A Couple Minutes
The Art of Loving (2025)
The Hardest Part
Messy (2023)
Baby Steps
The Art of Loving (2025)
Ladies Room
Messy (2023)
Move On Up (Cover)
Cover of Curtis Mayfield (originally from Curtis, 1970)
Ok Love You Bye
OK Love You Bye EP (2019)
It Isn’t Perfect But It Might Be
Bridget Jones: Mad About the Boy Original Motion Picture Soundtrack (2025)
Dive
Messy (2023)
Rein Me In (with Sam Fender)
People Watching (Deluxe) – Sam Fender (2025)
Man I Need
The Art of Loving (2025)
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