Lollapalooza Continues With Olivia Rodrigo, Weezer, T-Pain, Flipturn
Olivia Rodrigo performs on stage on day two at Lollapalooza. Friday, August 1, 2025 at Grant Park in Chicago, IL
Photo by Barry Brechisen
“Lollapalooza, are we ready to have a good f–ing time?” shouted pop star Olivia Rodrigo on stage Friday night during a headlining performance at Lollapalooza. “There’s so many incredible artists tonight. Thank you so much for coming. Thank you so much for having me.”
Rodrigo tore through her set Friday on the festival’s south end, continuing to flex a bit of a rock muscle alongside seminal alt rockers Weezer, who worked up their 1994 hit “Buddy Holly” during a guest spot with Rodrigo on the Lollapalooza T-Mobile main stage.
Temperatures were cool and rain free for the second consecutive day in Chicago, optimal festival going conditions and a rare respite from an otherwise sweltering Windy City summer.
Olivia Rodrigo performs on stage on day two at Lollapalooza. Friday, August 1, 2025 at Grant Park in Chicago, IL
Photo by Barry Brechisen
“I feel like it’s not too hot. As a ginger, these are the things I must think about,” said Irish singer songwriter Orla Gartland with a chuckle following a 45 minute performance amongst the trees on the Grove stage, long a favorite of concertgoers for the shaded break it provides in a section of Grant Park immediately adjacent to the Art Institute in downtown Chicago. “People were starting to scare me. They were like, ‘You’re gonna melt!’ But it was breezy and beautiful. And the crowd was amazing,” she said. “It’s really fun to get to do a festival and an aftershow in the same day. I feel very taken by my Lolla experience.”
Gartland got started as a YouTuber, busking as a teen in Dublin. Following a series of EP releases since 2011, Gartland released her sophomore full-length studio effort Everybody Needs a Hero.
In an industry constantly in search of the next big thing, often rendering the idea of artistry disposable, Gartland has thrived, carving out an identity while honing her craft methodically over time, building a sustainable and career.
Orla Gartland poses backstage following a performance at Lollapalooza. Friday August 1, 2025 at Grant Park in Chicago, IL
Photo by Barry Brechisen
“Those are really the moments where I think, ‘Yeah – it’s been a marathon not a sprint,’” said Gartland looking back. “It’s been a long time – but this is the only job I’ve ever done in my adult life. It’s been a slow and steady climb. But I feel really, really good,” she said. “This is the best festival, you know? And to get to play it? I’m definitely having a lot of those moments lately.”
Heading into Lollapalooza, Gartland performed on stage at Glastonbury earlier this summer, one of the most trendsetting festivals in Europe.
Arriving in Chicago, Gartland was taken by Lollapalooza’s unparalleled urban backdrop, a festival along the lakefront that takes over the downtown area of the country’s third largest media market, an immense footprint.
“It’s different. A lot of the festivals in the U.K. – not a lot of the big ones are in cities like this. This feels like it’s interacting with the city – we’re really in amongst the skyline,” she said. “It feels like the festival was built around an existing beast – not just put up in a field. It’s really, really cool. Watching the other stage and seeing the skyline, it’s very special.”
Orla Gartland performs on stage during a Lollapalooza aftershow at Bottom Lounge. Friday, August 1, 2025 in Chicago, IL
Photo by Ethan Chivari
Gartland shouted out Stranger Things star Joe Keery who performed in his guise as Djo for one hour on the festival’s south main stage Friday, recalling the way in which his 2022 hit “End of Beginning” – one now closing in on two billion streams on Spotify alone – lyrically references the city. “And when I’m back in Chicago, I feel it,” sings Keery, who spent time on the city’s north side as a student at DePaul University.
Florida-born indie rockers Flipturn pondered the idea of aging and growth, similarly referencing Lollapalooza’s midwest home on their 2017 debut EP Heavy Colors.
“Being able to play our song named ‘Chicago’ in Chicago at a Chicago festival – that was cool. That was a fun time,” said Flipturn multi-instrumentalist Mitch Fountain prior to the group’s sixty minute Lollapalooza set.
Flipturn performed on the Lolla stage Friday, sticking around for a Saturday night aftershow, giving them the rare luxury to experience the festival a bit and check out some other acts.
“Rüfüs Du Sol is one of my favorite bands ever. So, I’m very excited to see them,” said Fountain of the Australian alternative dance group who will headline Lollapalooza Saturday night. “I’m also looking forward to seeing Djo right after our set today,” added singer Dillon Basse. “I am really excited to see Olivia Rodrigo crush a festival set,” said bassist Madeline Jarman. “I want to see Junior Varsity tomorrow very badly,” added drummer Devon VonBalson.
Flipturn pose backstage following a performance at Lollapalooza. Friday August 1, 2025 at Grant Park in Chicago, IL
Photo by Barry Brechisen
Earlier this year, Flipturn released their latest studio album Burnout Daysdemonstrating a growth in songwriting while avoiding the sophomore slump.
“The songwriting process has always been pretty similar. We’ve always come up with a riff or some sort of chord progression and brought it to the band – build a structure, build a feel, you know? And then usually we’ll put lyrics to it once there’s a feel already there,” explained Basse. “But, really, what was different about this album was, I think, our demoing process – and our focus on tones and really honing in on a sound in the studio.”
New Jersey-born singer songwriter Gigi Perez has experienced viral success via TikTok, with her “Sailor Song” amassing over one billion streams on Spotify to go along with another 46 million views on YouTube.
Gigi Perez performs on stage on day two at Lollapalooza. Friday, August 1, 2025 at Grant Park in Chicago, IL
Photo by Barry Brechisen
Releasing her debut full length studio album At the Beach, in Every Life this past spring, Perez offered up a 55 minute early afternoon set on the T-Mobile main stage Friday.
“Lollapalooza! How y’all doin’?” said Perez, taking the stage armed with an acoustic guitar for opener “Please Be Rude.”
Backed by a tight three piece group, percussion drove the opener with Perez moving to electric guitar, rocking things up a notch during “When She Smiles.”
Dueling acoustic guitars drove “Sleeping” while Perez’s vocal shined throughout “Fable,” with Perez opting to let the music do the talking while keeping banter to a minimum during a rewarding early Friday set on the Lollapalooza stage.
Star Bandz poses backstage prior to a performance at Lollapalooza. Friday August 1, 2025 at Grant Park in Chicago, IL
Photo by Barry Brechisen
Maintaining a trend which began Thursday via the inclusion of Chicago-based acts like Ratboys and BJ the Chicago Kid, 17 year old Chicago rapper Star Bandz threw down a 40 minute stage closing performance Friday at Lollapalooza on the BMI stage.
“This is my first time coming. But I know that Chicago do show love to their artists. They do,” said Star Bandz backstage prior to her Lolla debut. “It means a lot. I’m so excited. And I’m so grateful for the opportunity to be here,” she said. “I am very excited and grateful.”
Appearing on the viral Sugarhill Ddot single “My Baby” in 2023, Star Bandz dropped her studio debut Estrella last year, taking a confident approach to her Lollapalooza performance Friday night.
“I just know that if I do what I gotta do today on the stage? It’s a big opportunity,” she said. “That’s all I can say.”
T-Pain performs on stage on day two at Lollapalooza. Friday, August 1, 2025 at Grant Park in Chicago, IL
Photo by Barry Brechisen
Rapper T-Pain performed to an immense crowd late Friday afternoon on the north end of the festival, with an overflow crowd cheering and screaming along over the course of a beautifully choreographed, energetic, engaging and extremely entertaining hour on the Bud Light main stage.
“What the f–k goin’ on?” asked T-Pain rhetorically from the Lollapalooza stage. “Ladies and gentlemen, my name is T-Pain! Welcome!”
T-Pain took the stage to the victorious sounds of Super Mario Brothers, maintaining a gaming theme on stage while working in some Pac-Man effects as he moved from “Up Down (Do This All Day)” to “Cyclone.”
Clad in fluorescents and backed by a tight dance troupe, T-Pain ran through one of Friday’s most memorable sets. Revisiting Michael Jackson’s “P.Y.T. (Pretty Young Thing),” he moved deftly into “The Good Life,” a Kanye West track he’s featured on which builds largely from a slowed down sample of the 1983 Thriller hit.
Bo Staloch poses backstage following a performance at Lollapalooza. Friday August 1, 2025 at Grant Park in Chicago, IL
Photo by Barry Brechisen
In an afternoon driven by throwback rock, pop and raucous rap, Nashville-based singer songwriter Bo Staloch took a more introspective approach to the festival setting.
“It’s a dream. A complete dream. It’s unbelievable,” said Staloch, pondering a Wednesday night after -show set alongside Alex Warren and a Thursday afternoon performance on stage at Lollapalooza. “We’re here this whole weekend which is pretty awesome. I feel very lucky. Last night, we saw Royel Otis. And they’re unbelievable. Some of my favorite songs. So, that was a lot of fun,” he said. “And I got to see some buddies – Winyah and Hey Nothing. And we performed the new single yesterday.”
Staloch’s forthcoming single “Born To” drills down on a simple but crucial concept during tumultuous times which often seem sadly bereft of love.
“I think it’s just a big old declaration of love – and I think I wrote it kind of in the romantic lens,” he explained. “But I think it can kind of transform into friendship or family – whatever kind of love you want to be declaring.”
Driven by honesty, Staloch’s authenticity was on full display during a pair of Lolla sets.
“Whenever I write, it’s all just subconscious thought. I don’t really try to write something in particular, it kind of just flows out of me,” he explained backstage at Lollapalooza. “And after I’m done writing the song, it’s like ‘Oh. That’s what I was feeling. That’s what was going on in my head.’ It’s like free therapy.”
