TVD Live: Lollapalooza at Grant Park, 7/29

12:29 PM: It’s been 532 days since I last photographed live music. Never did I expect my show back to be a festival, let alone the largest festival since Covid-19 changed our world, but as I walk into the grounds all I feel is immense gratitude to have the opportunity to get back to doing what I love to do. It’s emotional.

12:32 PM: As promoted and promised, Lollapalooza is requesting proof of Covid-19 vaccination in order to enter Grant Park. If you are not vaccinated, you must show proof of a negative Covid test within the last three days to be allowed into the grounds. Despite the precautions taken, rumors of fake vaccination cards swirl and there’s an undercurrent of fear felt by those of us who care.

1:14 PM: From first looks, it’s apparent that butt cheeks continue to be a top fashion choice for Lollapaloozans. It’s a sea of high-waisted jorts that stop coverage just atop the butt. Some things have remained the same post-Covid, and festival fashion is clearly one of them.

2:02 PM: Pop artist MAX brings the early fest energy to the LakeShore Stage. He’s in the crowd by the third song and covering Outkast (“Ms. Jackson”) by the fifth song.

2:13 PM: The Lolla decor is minimal this year and many of the banners are repeats from 2019. Also no printed schedules. I get it—why spend money on an event that might not happen?

2:32 PM: Now MAX’s wife is on stage and he’s serenading her. Audible “awwws” from the crowd.

3:02 PM: Orville Peck is mesmerizing. Is it his deep baritone voice? His cowboy hat and fringed face mask? All of the above? One thing is for sure: he’s bringing much needed new (and queer!) life to country music and it’s fun to watch.

3:18 PM: Heading north, I pass the Toyota Music Den and Absofacto playing all new tunes. “This is really fun for me so thank you,” he says.

3:24 PM: “It’s hot! What the fuck!” Olivia O’Brien exclaims to the crowd on the north end before diving into another heartbreak anthem, “Sad Songs in the Summer.”

4:11 PM: LP is a tiny package with a huge voice and even larger songwriting skills. She’s written songs for the likes of Cher, Céline Dion, and Rihanna to name a few. Now it’s her time to shine on the stage.

4:24 PM: The ’80s are back, Dayglow confirms with a synth-heavy set topped with a sax solo and a Tears for Fears cover (“Everybody Want to Rule the World”).

4:45 PM: Chicago Mayor Lori Lightfoot introduces Black Pumas, encourages the crowd to “spend a lot of money in Chicago,” and reminds everyone that “hate has no home here.”

5:37 PM: Well there’s not much more you can ask for in a band than Black Pumas. They are special: talented, soulful, natural entertainers. And it doesn’t hurt that lead singer Eric Burton is in head-to-toe Cubs gear and interacting with the crowd off the stage.

5:44 PM: It wouldn’t be Lolla without a Perry and Etty Lau Farrell sighting and I’ve just had my first in the Press Lounge. They’re taking photos and giving interviews.

6:09 PM: Perhaps inspired by my sighting of the man himself, I decide to venture to Perry’s Stage (rebranded this year as the Perry x Solana Stage). On cue, I have my first nipple sighting of the weekend. Cash Cash is “dropping the beat,” as the kids say, and I’m about to drop some Advil.

7:25 PM: Playboi Carti’s set has been a hot mess full of starts and stops and long pauses in between songs. It’s not entirely his fault: “Everybody take three steps back,” he pleads with the crowd. “People are passing out so they won’t start my music.”

8:14 PM: Kim Petras is serving us bubble gum pop and choreographed dance routines. Yas! I have a feeling she’s about to blow up.

8:46 PM: “It’s our party, we can do what we want.” Miley Cyrus has arrived. The crowd has expanded into a massive sea of (mostly unmasked) humans. A teen comes racing in from the outskirts shrieking “I came in like a wrecking ball!”

9:03 PM: Billy Idol is the first of many surprise guests during Miley’s set for a “White Wedding” duet. After, she addresses her fans, acknowledging how difficult it’s been without them. “I am who I am today—in my customized, bedazzled Gucci jumpsuit that was flown in from Italy,” she joked, “because of you.” Other special guests included Wiz Khalifa, G Herbo, Juicy J, and Kid LAROI. Miley also took time during her set to champion the LGBTQIA community and the #FreeBritney movement.

9:37 PM: Apparently Oliver Tree doesn’t know what festival he’s headlining. “What the fuck is up, Coachella?!” He screams from the GrubHub Stage. “Are you ready for a special guest, Coachella?” Lil Ricky, the special guest, doubles down: “What’s happening, Coachella?!”

9:52 PM: Leaving Grant Park, I take in Chicago’s big, beautiful skyline lit up like a rainbow. It’s the perfect exclamation to how exceptionally LGBTQIA friendly day one of Lolla’s 30th year has been. It’s wonderful to see such representation on and off the stage.

MAX