Olivia Dean reached a major career milestone when she headlined Lollapalooza Chicago on August 1. After the performance, the Grammy winner revealed she had spent the entire day crying as she tried to process the moment.
Olivia Dean Admitted She Spent the Day Crying While Processing Her Biggest Career Milestone Yet
Olivia Dean had previously performed in Austin during 2025, but this was her first time closing out Lollapalooza in Chicago, especially in front of a massive crowd of 97,000 people.
Dean described the performance as a full-circle moment after nearly a decade in the music industry. Dean shared on Instagram that she had spent the day crying while trying to process the milestone.
Olivia wrote, “My first time headlining a festival in America – 97,000 of you!! Truthfully I had been crying all day beforehand trying to process how we even got to this point. Thank you for sharing your love with me and thank you to everyone on my team who makes it possible for us to shine up there!!!!!”
“Love always!!!” Dean concluded
Dean’s emotional post also drew supportive comments from fellow musician Sam Fender and the official Lollapalooza account. Fender simply wrote, “Legend,” while Lollapalooza commented, “you are a STAR. Thank you for giving us EVERYTHING.”
Sam also joined Olivia Dean on stage, and the duo made fans happy with an incredible duet performance of the UK chart-topping song Rein Me In.
Olivia Dean’s schedule remains packed with upcoming performances. She will take the stage in Toronto, Canada, on August 4 and 5 before heading to Montreal for a show on August 7.
She will return to the USA on August 10 for a performance in Boston, and the rest of her schedule also looks packed in August.
TELL US – WHAT DID YOU THINK OF OLIVIA DEAN’S EMOTIONAL MESSAGE AFTER HER LOLLAPALOOZA PERFORMANCE?
