Artists To Watch At Lollapalooza 2025!

With so many great artists joining Lollapalooza's lineup this year, it's hard hard to keep up. WERS makes it easy. Check out this list of our favorite artists performing this year, and remember: if you donate to WERS today, you and a friend could win a trip to Lollapalooza! Just click here to donate!

Clairo

A constant on my playlist is indie-pop’s favorite it girl, Clairo. I first discovered Clairo through Mellow Fellow’s song, “Best Friend,” which name-drops Claire Cottrill (otherwise known as “Clairo”), and their later collaboration in the song, “How Was Your Day?” Having known Clairo before her rise to fame through TikTok audios soundtracking monthly photo dumps and Brooklyn male manipulator fit checks, I’ve enjoyed watching her artistic evolution from lo-fi bedroom pop to the more refined, introspective sound of her recent albums. 

My favorite songs from her include “4EVER,” “Impossible,” “Just For Today,” “Terrapin,” and most importantly, “Bags- Recorded At Electric Lady Studios.” Songs like these showcases Clairo’s talent for blending vulnerability with catchy, lo-fi melodies, further creating a sound that feels intimate yet universally relatable. Her collaborations with other indie-pop artists are just as compelling. Tracks like “Drown” with Cuco, “After Midnight” with Phoenix, and most famously, “Glue Song” with beabadoobee, showcases her versatility with different styles while leaving her distinct, emotive imprint on each piece.

With Clairo set to grace the stage at the upcoming Lollapalooza, her continued musical evolution only promises to further solidify her status as one of indie-pop’s most captivating and dynamic voices.

- Kelly Cheng, Staff Writer

 

Olivia Rodrigo

From Disney Channel to beloved festival headliner, Olivia Rodrigo has become one of the most prominent pop princesses in the last few years. I’m proud to say that I’ve been a fan since her days starring as the lead of an American Girl doll movie, but her music is certainly what I’m more passionate about. Her vocals and songwriting pulled me in when I heard her original song “All I Want,” which was used in High School Musical: The Musical: The Series. She’s everywhere, inescapable at award shows, on social media, and on my playlists. Rodrigo had breaking hits with her debut single “driver’s license” and its follow-up “deja vu,” and repeated the same success with singles from her sophomore album, guts, including “vampire” and “obsessed.” 

The interesting thing about Olivia Rodrigo’s music is that it grows with her as she ages. Sour is full of innocent ballads about first loves and teenage woes, where guts follow Olivia’s blossom into young adulthood and away from adolescence. She’s no “stranger” to writing about the darker side of femininity. If you’re into ballads and feeling your feelings, some of my favorites include “favorite crime” and “lacy.” Her standalone single for The Hunger Games: The Ballad of Songbirds and Snakes, “Can’t Catch Me Now,” is another example of how purely beautiful her songwriting is. 

As she continues her festival run and is gearing up for her next album release, Olivia has been blending influences from pop punk and riot grrl into her sets. A lot of her music, like songs “good 4 u” and “ballad of a homeschool girl,” already have promising roots in heavy guitars and grungy production, and she usually incorporates covers of No Doubt, Lily Allen, and Carly Simon into her sets. I’m personally excited to see what classic indie song she covers at Lollapalooza this summer!

- Ren Gibson, Staff Writer

 

Cage the Elephant

When I got my first car, the first thing I did was put Cage the Elephant’s Melophobia into the CD player. They have been a staple in my rotation for years, and I was so excited to see that they will be playing Lollapalooza this summer. With a career spanning two decades and a six album discography, Cage the Elephant have become an iconic alternative band — and for good reason. This will be the band’s fifth time performing at Lollapalooza, and their first time since 2017. 

Over the course of their six albums, Cage the Elephant have released songs that have shaped alternative music. From “Ain’t No Rest for the Wicked” from their first album, to “Shake Me Down,” “Come A Little Closer,” “Trouble,” “Ready to Let Go,” and beyond, the band has made genre-defining hits with each album, and their most recent release, “Neon Pill,” does not disappoint. 

Last summer, I had the opportunity to see Cage the Elephant on their Neon Pill tour. It was one of the best concerts I’ve ever been to! The band’s characteristic sound combined with their captivating stage presence created a show like no other. Frontman Matt Shultz is a true performer, giving his all to every moment, and every performance. 

Filled with hits like “Cigarette Daydreams,” new songs like “Metaverse,” and deep cuts that get the fans excited, their shows are filled with electric and memorable moments, from funny conversation to stunningly designed production elements. Cage the Elephant’s set is definitely one to see this year at Lollapalooza!

- Ahni Brown Harbin, Staff Writer

 

2hollis

I've gone from being a 2hollis hater to an unapologetic fan over the past year, and what marked this change was recognizing the authenticity in his artistry. 2hollis rose to fame through TikTok and Instagram reels, often soundtracking niche memes or grungy clips of indie sleaze aesthetic teenagers. His newest song, “style,” launched him into the broader experimental hip-hop and hyperpop soundscape. 

I’ve come to appreciate 2hollis’ music through his 2023 EP, whiplash / cliche. The two songs, “whiplash” and “cliche,” are, in my opinion, the best representations of 2hollis’ eccentric style in both character and sound. He masterfully blends underground rap, grunge garage rock, pop elements, and his own breathy, distinctive voice into tracks that emotionally resonate with listeners through his unapologetic intensity. At the young age of 21, 2hollis has built a discography of incredible successes with notable hits like “jeans,” “trauma,” and “crush.” 

Sure, some of his songs may be silly and nonsensical, and while his music videos are often highly stimulating and raunchy, 2hollis is undoubtedly pushing boundaries with his innovative, cutting-edge style. His bold fusion of aesthetics has cultivated a devoted cult following (including myself) drawn to both his chaotic creativity and raw emotionality. With his upcoming performance at Lollapalooza, 2hollis is poised to reach new heights, proving that his experimental approach is not just a passing trend but a defining force in the hyperpop landscape.

- Kelly Cheng, Staff Writer

 

Magdalena Bay

What brought me into synth-pop was discovering Magdalena Bay, and it was the best thing that has happened to me. Known for hits like “Killshot” and “Image,” Magdalena Bay is a synth-pop duo that I believe is one of the most creative and dynamic acts in contemporary pop music that deserves all the recognition and praise. Their most recent album, Imaginal Disk, took over my Spotify Wrapped and soundtracks the majority of my days. This album left me with happy tears and an intense variety of emotions, as there is so much to unpack— ultimately, it is a phenomenal masterpiece that brings me hope for pop music’s future.

Magdalena Bay’s innovative sound is rooted in their meticulous production techniques, blending lush analog synths, punchy syncopation, and glitchy, futuristic effects that feel both nostalgic and inventive. My favorite tracks are “Death & Romance,” “Fear, Sex” and “Cry For Me,” With Mica Tenenbaum’s ethereal vocals cutting through Matthew Lewin’s rich, textured instrumentals, Imaginal Disk proves Magdalena Bay’s commitment to pushing the boundaries of synth-pop and solidifying their place as visionaries in the genre. 

Set to perform at Lollapalooza, Magdalena Bay is poised to reshape the future of synth-pop and captivate an even wider audience.

- Kelly Cheng, Staff Writer

 

Djo

Djo is going to be “back in Chicago” in July for Lollapalooza! After a steep rise in popularity and his song “End Of Beginning” going viral, Djo, a.k.a. Joe Keery, is still much more than his most listened track. There is so much to be discovered in Djo’s discography, including my personal favorites of his debut album Twenty Twenty, “Personal Lies” and “Roddy.” The other-worldly and rock-influenced instrumentals make for a song that I can only imagine would be incredible to hear live. While fame has brought him from being a faceless presence in the music world to a star highlighted by his parallel career as an actor, he continues to make music the centerpiece of his artistic endeavors. 

Off his second album, DECIDE, “End Of Beginning” made it to center stage, but so much of that album expands on the success of the viral track. Many people look over the rest of the album, missing the haunting synths of “Half Life” and the deep bass drops of “Change.” Djo’s yet to be released, third studio album The Crux (Releasing on April 4, 2025) has already been heralded as his most thematically significant album to date. His solo tour and festival run this summer is sure to be a spectacle of his craft and his career is beginning to bloom. 

- Lucia Cinquino, Staff Writer

 

flipturn

flipturn has grown exponentially in the last few years – About three years ago, a friend of mine in high school once came up to me at the end of class to tell me about this band she had just gotten into recently. I was sent videos from her concert soon after, and when I saw her again she told me about all of their upcoming shows. This year, flipturn is going to be playing at Lollapalooza.

Lolla is always a summer highlight for music fans, and flipturn is such an awesome soundtrack for the warmer months. The band is based out of Fernandina Beach, Florida, and have done countless shows since their formation in 2015. Some must-know tracks before you catch them this summer are “August,” “Eleanor,” “Weepy Woman,” “Juno,” and “Poppies,” though some might say that every track is a must-know track. Their most recent album, “Burnout Days” was released in January of 2025, featuring twelve songs.

- Ana Achata, Staff Writer

 

Jane Remover

The anthem of Summer 2023 for me was “Search Party” by Jane Remover. The song comes off of their first album Frailty, and got me hooked on their unique sound. They have been compared to Ethel Cain, My Bloody Valentine, Slowdive, and more, but I think that what Jane Remover does is entirely their own. The hybrid of digicore, bedroom pop, and shoegaze that Jane Remover has developed through their first and second albums is unlike anything that I’ve ever heard, and keeps me coming back for more of their music. 

“Search Party” is the song that first got me into Jane Remover’s music. There was a week where I listened to it 86 times, and it’s still in heavy rotation on my playlists. Jane Remover’s first album, Frailty, which features the song, was placed at 47 on Pitchfork’s list of the best albums of 2021. In my opinion, it should be higher. The production is thought out in incredible detail, with motifs and riffs appearing throughout the entire album, connecting it together with a level of detail that left me in awe. Jane Remover followed up Frailty with their sophomore album Census Designated in 2023, which leaned more into the shoegaze genre. Their third album Revengeseekerz is set to be released this year, and the first single from the album, “JRJRJR,” is out now.

In concert, Jane Remover’s infectious enthusiasm and the dedicated energy of their fanbase always make their shows fantastic. On top of two headlining tours, they opened for JPEGMafia last year. Their set at Lollapalooza is definitely one to watch. If you want a taste of Lollapalooza, or are a fan of Jane Remover, be sure to check out their show at the Sinclair on May 2. 

- Ahni Brown Harbin, Staff Writer

 

Bladee

I downloaded SoundCloud in high school just to listen to Drain Gang; however, it wasn’t until freshman year of college that I came to appreciate Bladee’s music. Bladee found his breakthrough by collaborating with fellow Swedish experimental rappers and producers, becoming a legendary member of the 2010s underground music collective, Drain Gang. Now pursuing his solo career, Bladee is known for his dreamy, hyperpop-infused, alternative rap songs. Some of my favorite tracks include “Mallwhore Freestyle,” “Reality Surf,” and “Oxygen.”

His newest album, Cold Visions, is a testament to his musical evolution and experimental spirit, showing how he’s constantly pushing the boundaries of the genre he helped cement. Beyond Bladee’s solo projects, his collaborations with other cutting-edge artists are just as groundbreaking. Tracks like “Rewind” with Charli xcx, “take me by the hand” with Oklou, “Amygdala” with Ecco2k, and my personal favorite, “Hocus Pocus” with Yung Lean, all showcase Bladee’s versatility and undeniably avant-garde style.

Now set to perform at Lollapalooza, Bladee continues to inspire and innovate by seamlessly blending elements into his production to craft a sound that feels otherworldly and transcendent.

- Kelly Cheng, Staff Writer