Am I getting too old for Lollapalooza? As a 33-year-old Black man who covered all four days of the massive music festival, I struggled to find where I belong. Even with Black artists I enjoy in the lineup, listening to certain songs with certain lyrics can feel awkward in the majority white festival crowd.
My love for live music is what keeps me going back to Lollapalooza year after year. I feel like I’m witnessing magic each time. Most of the Black performers on this year’s lineup proved why we need a bigger presence. Doechii should’ve headlined the festival.
In this piece, I’ll recap Lollapalooza 2025 as I experienced it. I’ll also share some of the conversations I had with artists along the way.
On Thursday, I interviewed singer-songwriter Durand Bernarr before his set on the T-Mobile stage.
“I’m more excited about the people that don’t know who I am, so that they can get their first-hand experience,” Bernarr said. “Those are my favorite patrons.”
That’s a good mindset to have because, needless to say, there was a crowd of young white guys in front of me during his performance. They stayed the whole set and noticeably enjoyed the show. Bernarr ran through songs like “Freefall,” “Overqualified,” and “Weird.” He also entertained the crowd with a DJ set, under his DJ name: DJ TBD (aka Bra Coley). The “TBD” stands for “The Best DJ.
“I have an extensive catalog where everyone can sing along, Bernarr told me, “and then there are songs that I just absolutely will not do because it’s a mixed crowd. It’s mixed company.”
He’s talking about “Mango Butter.” The song, a fan favorite, goes: “I’m a bad bitch and I’m that nigga.” I voiced my concern to Bernarr, saying as a Black man I will always cringe hearing white people sing the N-word. I then asked if he would be performing “Mango Butter.” He said no, without any hesitation.
“The last thing I want to do is make my people feel uncomfortable because we’re outnumbered and I’m singing a song that is not inclusive,” Bernarr said.
Not many other Black artists, particularly rappers, took that approach.
For example, on Saturday, notable rapper BossMan Dlow used the N-word repeatedly during his afternoon set on the Lakeshore stage. I was happy to see him perform; his songs “Phil Jackson” and “Finesse” are in my regular rotation. But his set reminded me of Bernarr’s courageous and socially-aware choice to take the N-word out of his set.
It was an eerie feeling watching an artist repeatedly say the N-word while I stood in a crowd of young white boys who proudly slung around the N-word while reciting the lyrics.
I did get a chance to interview BossMan Dlow before his set. We talked about it being his first time at Lollapalooza, and how he was excited to bring energy to the Lakeshore stage.
“It’s, like, Rolling Loud type of vibes, so I’m f-cking with it, fa sho,” he said.
I did get a chance to ask him if he would censor his lyrics to fit the crowd of the festival. BossMan replied, “Nah, I’ma come with that big za energy everytime. Might add some songs if anything.”
Meanwhile, Chance the Rapper used his set to entertain and uplift the crowd while simultaneously condemning white supremacy — all at the same time. His “surprise” set took place at the Perry stage about an hour after BossMan Dlow.
Although Chance launched into his set with some of his certified bangers, “No Problem,” “All Night” and “Cocoa Butter Kisses,” the rapper from 79th performed a new track called “Tree” featuring Smino and Lil Wayne from his forthcoming Star Line album. He started off rapping acapella, with the lyrics going across the big screen behind him.
My mama used to always keep a lil’ bit of ‘dro
The incense in the window while she foldin’ our clothes
And though life will have its issues, there would never be
A problem with the weed
She told me “Son, don’t worry, don’t you have no shame
There’s gonna be frustration in this white man’s game
And they’re gonna have us tied up once it’s legalized
Because it is a tree”
Wow. I’ve never been so proud and felt so awkward at the same time! I was amazed that the 32-year-old rapper had the courage to call out white supremacy not only on the record, but also in a crowd of white people.
Did Chance use the N-word during his set? Sure. It’s in the refrain of 2016’s “No Problem.” But Chance didn’t say it every 10 seconds as an adlib like BossMan Dlow did.
This type of stuff didn’t bother me when I was younger. Now, as the father of a 9-year-old boy, I do feel like the constant chanting and adlibbing of the N-word in music is a bit unnecessary; it can be an invitation for non-Black listeners to join along.
I interviewed Chance and his brother Taylor Bennett before his set. It’s been six years since Chance last released a full music project, and he’s betting on himself again. This time, his sophomore album Star Line is a physical CD; once copped, you can tap the CD with your phone and listeners will receive a secure link to play and bluetooth the record. Release day is Aug. 15.
“Man, we really independent,” Bennett said. “We really came up off selling CDs at high schools and popping up and giving away music for free, and we doing the same thing on a whole nother level.”
Chance said Lolla hit him up about a week before its start, asking him to do his own set in anticipation of his upcoming album, which he’s been working on for the past few years. He said he’s been prepping his fans for what’s to come by dropping loosies and writing exercises and contextualizing the new music through audio-visual experiences.
“Even before Coloring Book or Acid Rap, I gave my music to people for free, and my fans always loved that and have stories about how they value my music differently just based on how they got it,” Chance said. “So I’ve been trying to experiment with different ways of getting the stuff to people. And now we’re here. I think, at the very least, my fans have a sense or an idea of the style, the writing techniques, the use of literary devices, the conversations about the Diaspora.”
OK, Let's talk about T-Pain for a minute
This one is hard to admit, especially because many people — including myself — are calling for more Black artists in the lineup. When it was announced that T-Pain was coming to Lolla, some media outlets and Black people said he should be a headliner.
After what I just witnessed, T-Pain is not a headliner, y’all. I’m sorry.
On stage, T-Pain talked about being tired, hot and ready to go, multiple times, in between songs.
What was even harder to endure was listening to him sing covers. In 2023, he released an album of himself covering popular tracks, called On Top of The Covers. Doing 15 minutes of covers, the whitest songs possible at that, was a bit disappointing.
T-Pain performed “Don’t Stop Believin’” by Journey; of course, the crowd loved singing along to that. He also did Sam Smith’s slow record, “Stay With Me.” Then, he sat down onstage and sang a country record, Chris Stapleton’s “Tennessee Whiskey. As this was happening, I watched what looked like hundreds of fans leave his set.
It was especially excruciating seeing him finish his set with the dance club songs I’ve most hated: Baby Bash’s “Cyclone,” Pitbull’s “Hey Baby (Drop It to the Floor),” DJ Khaled’s “All I Do Is Win” and Flo Rida’s “Low.”
T-Pain’s setlist is an example of a successful Black artist trying his damndest to fit in at a predominantely-white festival. They end up toeing the line between staying true — by performing the songs that their day-one fans want to hear — and appeasing the massive white crowd the festival attracts. Now, he did the classics like “I’m ‘n Luv (wit a Stripper),” “I’m Sprung” and “Bartender.” He ran through the features and the choruses he’s known for: like Plies’ “Shawty,” Chris Brown’s “Kiss Kiss,” and Kanye West’s “Good Life.”
But he knocked those out early in his set. That was a mistake.
Change up the order, and give Teddy a smaller stage, and I believe T-Pain would have flourished. No covers, though.
What I'd like to see more of
I would love to personally see a stage totally dedicated to Chicago performers for the whole weekend. When you look at the landscape of Chicago music, there are more than enough artists, across different genres, that could easily fill a weekend’s worth of performances. The Chicago Made Showcase on Sunday was great, but the set time was split between multiple artists.
There was another local artist showcase near the Buckingham Fountain that was put on by the John Walt Foundation. I missed Friday’s lineup, which included boy band Pivot Gang, artist Jean Deaux and more, but I caught Sunday’s, which was hosted by dance artist iAmDLOW and rapper Pinqy Ring.
I spoke to DLow before performances began.
“All the work that they’ve [John Walt Foundation] have been doing for the community, for the kids, giving them a platform, giving them new experiences, that’s life changing,” he said.
Chris “Classick” Inumerable, founder of the Grammy Award-winning Classick Studios, was in attendance. I asked what his role with the showcase was: “I’m a fan first.” He was there to support the foundation, which was launched in memory of the late Pivot Gang rapper John Walt.
“Big or small, it’s an opportunity,” Inumerable said about the John Walt Foundation showcase. “Anything that sheds light on the next generation, is the best thing ever.”
He added, “Let’s keep pushing the culture for the next ones to win, and give them a platform.”
