Photo Essay: In with the new at Lollapalooza 2022

The 27-year-old rising star De’Wayne released his first album and toured with Willow Smith all in one year. Now, one year later, the genre-bending singer performed on the T-Mobile stage at Lollapalooza 2022, the famous Midwest music festival that skirts the shore of Lake Michigan. 

This Chicago festival, being one of the longest-running music festivals in the country, has attracted large crowds year after year. To that end, this Lollapalooza was no different than years prior; an average of around 100,000 attendees per day flocked to Grant Park this summer for four days of non-stop music. However, the artists that made up the lineup fueled a number of polarizing reactions. 

While many young people were happy with the number of up-and-coming artists performing, many older attendees didn’t feel satisfied with a lineup of unrecognizable names. Metallica, mixed in with a couple of the other headliners, were the only means of incentivizing older festival-goers to buy tickets. 

Just as Lollapalooza has aged — its 31st anniversary was this year — so has its initial 1991 crowd. Music festivals aren’t catered to older generations; a festival like Lollapalooza is a young adult playground. Every summer, Grant Park brings in the newest generation of music-lovers. With more young people than ever before listening to the indie genre, or what is dubbed “underground” music, festivals like Lollapalooza are bound to feature indie artists. 

The rise in streaming platforms has enabled more young people to produce indie music, meaning that more young people are able to listen to indie music. Music has been made more accessible, with seemingly limitless options for listeners. And the rising number of young musicians producing their own music out of their bedroom has only been exacerbated by the initial COVID-19 lockdown. 

In order to cater to the tastes of the demographic that buys out the lion’s share of festival tickets, Lollapalooza 2022 brought in young artists like De’Wayne. The festival’s lineup gave lesser-known artists a chance to play in front of a large crowd — many for their first time. Throughout my four days spent at the festival, I sat down to talk to a few of these up-and-coming artists. 

De’Wayne

It was an emotional day for the 27-year-old singer. As I walked with him to the pine tree just outside of the press lounge for a portrait, the artist told me that he cried immediately after his set. 

“I knew I would be at Lolla playing on the main stage. Even though I’m emotional about it, I knew it would happen. I hope that doesn’t sound egotistical. I always knew,” De’Wayne said.

During his mainstage performance, De’Wayne exuded an air of onstage confidence akin to that of a seasoned performer. 

“I feel like this year I really found out how to make really good songs … When ‘DIE OUT HERE’ came out I was like, ‘this is phenomenal.’ I feel like I found out the De’Wayne code … so that was a really good moment for me.” 

The confidence that I saw from him onstage did not waver throughout our interview. He was a natural in front of the camera.

Actually, De’Wayne has always felt this self-assured — even while he was forced to work three jobs in L.A. as a 19-year-old trying to break into the industry.

“I had no money and my family was calling me every day (after I moved). I would tell them that I was going to do all these specials and that I was going to get my music heard even though I was very broke and I hadn’t eaten in four days,” De’Wayne said.

“I felt good about my chances. I always knew. I talked to a lot of people and artists. There was never a doubt in my mind even though I went through hell. I met a lot of artists who haven’t had hard times — not that life was easy for them. I’m really thankful for the journey and really having to work to earn everything.”

Zoe Wees

Zoe Wees is a German pop singer-songwriter, most famous for her hit “Control” which was popularized as a sound on TikTok. 

Just like De’Wayne, Wees performed on a main stage. However, her experience didn’t go as smoothly. 

For the duration of her performance, the singer was unable to hear her own voice through the microphone. While that unfortunate audio issue caused stress to the singer during her first performance at Lollapalooza, Wees was still able to take away some positive things from the experience.

“I think that this stage especially is one of the biggest stages that I have played on. I am very proud that I was able to share the stage with so many great artists,” Wees said. “I’m proud that I’ve worked pretty hard the last year and very happy to be able to do what I’ve always wanted to do.”

While she has always loved to sing, Wees has only been singing in a studio for two years. She started producing music at the beginning of the COVID-19 pandemic in 2020. 

“I’m very proud to be here. Who would’ve thought, right?”

The sheer accomplishment of performing at Lollapalooza after only two years in the industry outshines even the worst onstage hiccup. The young artist is grateful to have performed at the festival — audio issue or not.

Calder Allen

Calder Allen is a 19-year-old country singer-songwriter from Austin, Texas. Even though singing and guitar became a recent hobby, and now a profession of his, Calder has music in his genes. He is the grandson of the famous singer-songwriter Terry Allen.

Similar to Wees, and many rising singers of this generation, Allen picked up a guitar for the first time while stuck in quarantine during the COVID-19 pandemic. 

Before the pandemic hit, Allen actually aspired to play basketball in college. 

“I definitely didn’t think (I would be doing) music when I was younger,” Allen said.

“Musically, I am super proud of the record that just came out. I think it’s a good starting point to let people know that I am doing music now.”

Allen didn’t play on a main stage like De’Wayne and Wees — but the mere fact that he performed at Lollapalooza at his age is impressive enough. As a 19-year-old with raw talent and ambition, this Lollapalooza debut is only the beginning for the young artist. 

“I think life-wise I have a good grip on where I am going and who I want to be, and I feel that’s pretty special at a young age. I am very grateful for that.”

Flipturn

Flipturn was formed in 2015 by bassist Madeline Jarman, lead guitarist Tristan Duncan, and singer Dillon Basse in Madeline’s garage. Since 2015, the band has welcomed two additions: guitarist/synth player Mitch Fountain and drummer Devon VonBalson. 

While sitting with the band, their strong bond and love for one another as friends was apparent. 

“I found people to grow with,” VonBalson said. “These are good people to surround yourself with.” 

Because the group formed while the original members were still teenagers, the band has been able to grow up together and eventually bring VonBalson and Fountain into their close-knit circle.

As I talked with the band, time and time again, the conversation went back to friendship and the fun of making music with your best friends. 

The group was grateful for the opportunity to branch out of Florida and perform across the United States, including at Lollapalooza this year.

This fall, the Florida natives plan to continue doing what they’re doing — enjoying each other’s company while making music — but this time the music-making won’t be done in a garage. The group is set to go on tour, performing in 35 cities across the country beginning Sept. 16.

Jesse Jo Stark

Jesse Jo Stark is an alternative singer-songwriter just getting her start in the industry. 

While she has only recently garnered musical fame, Stark has been in the spotlight since she was a young girl. Cher, the “Goddess of Pop,” is her godmother. Her parents, Richard Stark and Laurie Lynn Stark, are high-end fashion designers that founded the company Chrome Hearts. 

Like all the other up-and-coming artists interviewed, it was Stark’s first time performing at Lollapalooza. However, this doesn’t mean Stark is a stranger to the limelight. Throughout her youth, her family’s fame added an extra layer of outside scrutiny on her.

At her current age, Stark says she finally feels comfortable in her own skin.

“I’m really enjoying the age I’m in. I prefer just wearing my own skin and owning everything you have, because we really only have ourselves to offer and that’s cool. That’s what you realize when you get older — or at least every day for me. I’m still figuring it out. I’m happy,” Stark said.

“I think experimenting comes with age. I think I was a bit angrier in my early twenties. Now I can be angry and sweet.”

Jesse Jo Stark, Flipturn, Calder Allen, Zoe Wees and De’Wayne are just a few of the young up-and-coming artists that Lollapalooza featured in their lineup this year. Many of those interviewed have found music to be a catalyst for their personal growth as they navigated young adulthood — and, for a few, as they navigated young adulthood among the loneliness of the COVID-19 lockdown. 

As more young people picked up or returned to music at the beginning of the COVID-19 pandemic, an influx of indie music produced in garages and bedrooms reached streaming platforms. Many of these artists are a product of time spent alone in a room with only themselves and their voices to keep company. Lollapalooza’s 2022 lineup reflects the growing interest and popularity of the young indie artists of this generation.

Co-Managing Photo Editor Tess Crowley can be reached at crowlete@umich.edu.

Co-Managing Photo Editor Grace Beal contributed to the interviewing in this article.