Lollapalooza Day 2 Highlights: Janelle Monae Empowers, Chance the Rapper Joins Death Cab For Cutie & More

Tim Mosenfelder/Getty Images.

Janelle Monae performs during 2019 Lollapalooza day two at Grant Park on August 02, 2019 in Chicago.

No matter the set time, every artist on day two of Lollapalooza Friday (Aug. 2) brought their A-game, and the crowds reciprocated. Headliner Childish Gambino brought fireworks, Bishop Briggs enlisted a choir and Death Cab For Cutie even had Chicago's own Chance the Rapper.

With so much to take in on Lolla's second day, Billboard shares 13 highlights below.

Picture This' Irish pride

Hailing from Kildare, Ireland, Picture This felt right at home in Chicago thanks to the rowdy crowd that helped them kick off the second day of main stage acts. Fans waved Irish flags in the air as they chanted "Ole! Ole! Ole!," almost making Picture This' 40-minute set feel like a headline show in their home country -- and they loved every second of it. 

"As we say in Ireland," frontman Ryan Hennessy said, "This is craic, Chicago."

Alec Benjamin's humility

Those who hadn't seen Alec Benjamin prior to Lollapalooza discovered that the 25-year-old singer is as pleasant as his falsetto singing voice. Not only was he sporting a simple outfit of jeans and a plain white sweatshirt (which was impressive in the 80-degree heat), but he also told the audience, "This is probably one of the coolest days of my life" and dedicated a song to his mom and sister. After all the sweet talk and singing, Benjamin couldn't help but celebrate his latest milestone: "I'm not trying to flex, but I just hit a million followers on Instagram," he said. "So that's pretty cool."

Against the Current's Warped Tour-like set

Though the pop-punk band played the stage that's tucked away in the trees, Against the Current's high-energy performance brought fans back to the days of dancing on hot pavement at Warped Tour. Frontwoman Chrissy Costanza's vocals soared as she thrashed around the stage, and in true Warped fashion, she even went barefoot for their closing song, "Wasteland." 

Conan Gray's lovelorn attitude

Conan Gray brought his super-personal lyrics to life on the Bud Light stage, using nearly every opportunity to make a playfully resentful remark about love.

"Y'all ever seen a couple and been like, 'I want to throw up all over you?'" he said before his hit "Crush Culture." But even when he flicked off cameras while singing "The King," Gray's attitude was endearingly relatable.

Maggie Rogers' nonstop dancing

"Let's find out who came here to take pictures and who came here to dance!" Maggie Rogers told the crowd after making it very clear that she was there for the latter. She literally ran on stage (in appropriately bright tie-dye orange and blue getup) and even danced her way through slower tunes like "Overnight." Her energy was so infectious that an unexpected technical issue during "Alaska" turned into a giant sing-along, making for one of the most fun moments of her whole hour-long set.

21 Savage and Childish Gambino's surprise team-up

In his second Lolla appearance in three years, 21 Savage delivered more than two dozen hits in just 60 minutes. After causing a monumental wave of energy from the crowd with his verse from Post Malone's “Rockstar" about halfway through, the rapper caused another uproar with an early appearance from Childish Gambino (who was wearing what looked like an inflatable airplane neck pillow, slippers and an arm sling -- all of which he ditched when he closed the festival on the same stage later). 

The two teamed up for their collaboration “Monster" from 21 Savage's 2018 album I Am > I Was.

Matoma's main stage-worthy moment

The Norwegian producer turned his evening Perry's stage set into what felt like a late-night
affair, compete with pyrotechnics and special guests. While he owned the stage solo with his impressive piano skills and hype man abilities, Matoma had some friends join in the fun: Noah Kahan for their "Hurt Somebody" remix, MAX for their collaboration "Lonely" and Chicago native Josie Dunne for their recent team-up "Sunday Morning."

Janelle Monáe's cry for equal rights 

Before diving into "Tightrope," Janelle Monáe reminded the crowd that the country is fighting for the rights of women, the LGBTQ+ community, people with disabilities, immigrants and people of color.

"We're fighting against the abuse of power," she said before making the biggest statement of all. "We're fighting to have Donald Trump impeached." Her prowess matched her passion, and even after going five minutes over her hour set time she didn't feel she was done sending her message: "I wish I had more time!"

Death Cab For Cutie's Chance surprise

After playing most of their own hits, Death Cab For Cutie gave the Chicago natives in the crowd one of their hometown heroes. Chance the Rapper walked out to a frenzy of excited screams, reminding fans that it was the first time he'd be performing his Death Cab collab "Do You Remember" off The Big Day with the alt-rock band.

"This might be a moment in history," Chance declared.

NF's live debut of "When I Grow Up"

The Lake Shore stage crowd was electric from the second that NF took the stage with his fiery The Search lead single "Why." But fans were especially excited to hear his latest single "When I Grow Up," as it marked the first performance of the song -- which NF was equally pumped about, jumping up and down throughout the whole performance.

Bishop Briggs' church choir

Though Bishop Briggs needed no assistance to make her performance powerful, she enlisted a full choir -- white robes and all -- to bring her song "The Champion" to the next level. Before the group exited the stage, Briggs showed her appreciation with a group hug.


I AM CRYING @lollapalooza ------------------------

A post shared by Bishop Briggs (@thatgirlbishop) on

Tame Impala's entrancing visuals

"I'm especially appreciative that you're here because you could be seeing Childish Gambino right now," Tame Impala singer Kevin Parker couldn't help acknowledging to fans who chose to be at their headlining set. "But hey, we're gonna try to make it worth your while."

Fans likely forgot anyone else was on stage, though, as the group's trippy multicolored visuals were an entrancing addition to their psychedelic rock tunes.


"Gets me every time These close encounters" ------ @tame__impala photo by @rohofoto.

A post shared by lollapalooza (@lollapalooza) on

Childish Gambino's inspirational speech

Childish Gambino had a firework display and plenty of energy to make his main stage headlining set memorable, but it was evident he wanted to leave fans with more than just a show. He gave fans a call to action to "be the visionary we are waiting for" before diving into "Have Some Love," and before leaving the stage he reiterated the sentiment. "Remember when I say you are the future," he said. "Love yourself."

Additional reporting by Melinda Sheckells.

Festivals 2019


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