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Olivia Rodrigo and Sabrina Carpenter have been announced as headliners for the upcoming Lollapalooza music festival in Chicago, which will run from July 31 to August 3. The festival, known for its impressive lineup, will also feature stars like Tyler, the Creator, A$AP Rocky, Doechii, and Luke Combs. The news has generated a buzz online, especially among fans who are still speculating about the past connections between Olivia and Sabrina, both of whom were rumored to have been linked to their mutual ex, Joshua Bassett.
The mention of their names together at such a high-profile event has reignited chatter on social media. Fans quickly referenced the alleged tension between Olivia and Sabrina over Joshua Bassett, with one fan humorously noting, “Joshua Bassett is crashing out right now,” and another jokingly stating, “In my head Olivia Rodrigo and Sabrina Carpenter are still beefing over Joshua Bassett.”
Both Olivia and Sabrina shared their excitement on social media about the Lollapalooza performance. Sabrina posted an enthusiastic reaction on her Instagram Story, while Olivia expressed her excitement on Instagram with a joyful “Wohoo!!!” accompanied by pink heart and flower emojis.
The timing of this announcement is significant as Olivia is currently on her GUTS world tour, which began in February 2024 and runs until July 2025. Sabrina, on the other hand, is also on her own tour, the Short N’ Sweet tour, having performed in cities like Birmingham, Glasgow, Manchester, and Paris.
Olivia and Joshua were rumored to have dated while working on High School Musical: The Musical: The Series, leading to much speculation around the release of Olivia’s breakout hit Driver’s License in January 2021, which many believed to be about their breakup. Sabrina, who was linked to Bassett shortly after, was also mentioned in the song’s lyrics by some fans, especially the line about a ‘blonde girl.’
Currently, Olivia is dating actor Louis Partridge, while Sabrina was in a relationship with actor Barry Keoghan in 2024. Despite the past drama, both singers continue to shine in their individual careers and are set to deliver unforgettable performances at Lollapalooza.