Pop icon Sabrina Carpenter was the last, but certainly not least, artist to headline the T-Mobile stage at Lollapalooza 2025. She put on quite a performance with an elaborate set, an outfit change, a clear theme, and, of course, her exemplary vocal styling.
The first view festivalgoers had of Carpenter was a prerecorded video that played as if she were a retro nightly news anchor.
“We’re back reporting live from Chicago,” Carpenter said in the video. “Well, folks, we’ve reached the end of our news program, and it’s been another sweet day in Chicago. So stick around, we’ve got a great evening of television lined up for you. For now, we say, ‘goodbye, Chicago!’”
Sticking to her retro aesthetic, Carpenter’s set and the backup dancer costumes all looked like they came straight out of “Hairspray.” After the intro video built quite the anticipation for Carpenter herself, she opened with “Busy Woman.”
“Chicago, the first time I played here was for a room of 300 people,” Carpenter said. “And when I wrote that last song, I could hardly picture anyone singing it, let alone so f—ing many of you, wow.”
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Carpenter noted how far she’s come since her last Lollapalooza appearance in 2023. That year, she made her appearance at 5:45 p.m. on Friday at the Lakeshore stage, which was previously denoted as Coinbase. She credited her ability to now headline on T-Mobile to her fanbase and thanked the crowd for their support.
Keeping energy high moving into the middle of her set, Carpenter pulled a surprise out of her back pocket.
“Does anyone want to dance tonight?” Carpenter asked. “I had this idea, let’s see how you feel about it. I guess I just thought it would be really, really fun if I could bring out some friends for you guys and we could just let loose, right? We could just groove.”
As Carpenter was giving her introduction, the beginning chords to “Let’s Groove” by Earth, Wind & Fire started to play just as she announced they would be joining her on stage. The band flooded the stage and, together with Carpenter, continued their hit song.
Following “Let’s Groove,” Carpenter requested one more collaboration and performed “September” with the band. During this takeover, the crowd was seen moving and grooving to the funky beat that still fit in with Carpenter’s overall retro theme.
Carpenter’s music stands for itself, earning her two Grammy awards and several other accolades. Her performance remained mostly upbeat with songs like “Man Child,” “Nonsense” and “Feather,” but Carpenter took time to slow things down with emotional ballads like “Sharpest Tool” and “because i liked a boy.”
However, what made Carpenter’s Lollapalooza performance stand out was not her ability to sing a good song — although that certainly helps — but rather her ability to put on a show.
During almost every song, Carpenter was dancing around the stage to rehearsed choreography, backed up by a team of equally talented dancers who constantly gave the audience something to watch.
Additionally, she kept her themes of retro television programming alive throughout the entire set with “commercials” that would help introduce songs or allow her time to complete a costume change. There was never a dull moment during her hour-and-a-half show, which is not an easy feat.
Carpenter geared up for her big finale with a mix of old and new, popular and niche. While performing “Juno” off her most recent album, “Short n’ Sweet,” Carpenter added a nod towards Chicago’s bean landmark and tossed a miniature version into the crowd. Moving swiftly into “Please, Please, Please,” Carpenter had practically the entire audience singing along to the addictive tune that has taken over many radio stations in the past year since its release.
During her performance “Don’t Smile,” Carpenter left the main stage and appeared on a lift in the middle of the crowd, allowing those further back to catch a glimpse of the artist. As she wrapped up her headline set with “Espresso,” fireworks shot out the back of the T-Mobile stage, signifying both the end of her appearance but also the end of Lollapalooza 2025.
As audience members streamed out, the tracklist for Carpenter’s new album, “Man’s Best Friend,” flashed across the screen, leaving the audience with something to look forward to.
Carpenter has certainly earned her spot as a headliner and has come a long way since her evening time slot two years prior. As she continues to release music, she will most definitely be an artist to keep an eye out for.
