The Women of Lollapalooza: A Retrospective Recap

By Montserrat Vazquez-Posada and Meredith Fuentes

One of the largest music festivals in the world, Lollapalooza is a Chicago-based flurry of jam-packed performances, good eats and chaotic crowds that impressively spans four days. 2019’s lineup brought 400,000 people–decked out in neon and slathered with glitter–to Grant Park at the city’s center for a hot and sunny long weekend of live music. 
While this year’s headliners did not spark as much excitement in festival-goers as in previous  years, the overall lineup was stacked with up-and-coming artists determined to make a name for themselves. Most notably, female artists brought their A-game to the stage and dominated the festival. 

In honor of these empowering women, here’s an overview of our favorite female performers  who strutted their stuff and commanded crowds at Lollapalooza 2019. 


THURSDAY, DAY 1

Lennon Stella

Image courtesy of Sydney Gawlik/Lollapalooza 2019

Image courtesy of Sydney Gawlik/Lollapalooza 2019

Lennon Stella kicked off the weekend with an intimate 45-minute set on the Bud Light Stage. The 19-year-old Canadian from Oshawa, Ontario had never been to Lollapalooza before, but you wouldn’t have been able to tell from the way she confidently worked the stage. With lyrics to her songs displayed on the huge flatscreen behind her, Stella’s set was an afternoon sing-along that drew in fans and first-time listeners alike. She clearly threw herself into every song, but was especially passionate about the catchy fan-favorite “La Di Da.” Swaying around stage with her long hair accentuating her every movement, Stella leaned into the audience during the happy-sad anthem as they joined her in singing the titular lyrics “la da da di da.” 

- Montserrat Vazquez-Posada

Normani

Image courtesy of Charles Reagan Hackleman/Lollapalooza 2019

Image courtesy of Charles Reagan Hackleman/Lollapalooza 2019

Normani's performance was simply eye-catching, and not just because she rocked a glimmering two-piece set in baby blue. What gave her an edge over the weekend's other performers was her ability to transform a midday slot at one of Lolla’s smaller stages to a full-blown stadium performance as she stood surrounded by her backup dancers who complimented her look in same-color leather sets. From the get-go, Normani showcased her countless years of dance training with her choreography to her opening number, “Checklist.”  

- Montserrat Vazquez-Posada

Hayley Kiyoko

Image courtesy of Santiago Covarrubias/Lollapalooza 2019

Image courtesy of Santiago Covarrubias/Lollapalooza 2019

With a good-enough voice and a small army of loyal fans, any artist can secure a set at music festivals like Lollapalooza. It’s women like Hayley Kiyoko, however, that draw an unmistakable  distinction between a set and a performance. She could’ve gotten away with walking back and forth across the stage and letting her vocals do all the work – like many others on this year’s lineup – but Kiyoko came to stun. With a laidback swagger and sharp motions perfectly synchronized with her two flannel-clad dancers, Kiyoko was the best cure for any underwhelming set. Pop tracks from her 2018 debut album “Expectations” have a way of unraveling her vulnerability that proved to the Lolla crowd that her set was a safe space filled with positive energy. 

- Montserrat Vazquez-Posada

FRIDAY, DAY 2

Tierra Whack

Image courtesy of Greg Noire/Lollapalooza 2019

Image courtesy of Greg Noire/Lollapalooza 2019

Tierra Whack took to the American Eagle stage on Friday for a midday party. Performing a medley of minute-long fan-favorites off “Whack World” such as “Hungry Hippo” and “Pet Cemetery,” Whack had everyone’s undivided attention during her short set. She sported an oversized shirt with a cartoonish version of her face, which was accompanied by kooky visuals reminiscent of “Whack World.” The artist wanted people to know her set would be far from normal. Her energy infected anyone who stopped to watch her performance before heading to the far north or south entrances to gear up for the headliners. With fans screaming lyrics back to her face with a force as unpredictable as she is, there’s no surprise Whack called Lollapalooza her “best crowd ever.”  

- Montserrat Vazquez-Posada

Maggie Rogers

Image courtesy of Sydney Gawlik/Lollapalooza 2019

Image courtesy of Sydney Gawlik/Lollapalooza 2019


Maggie Rogers’ unique sound and style were on full display during her Saturday afternoon set. Rogers’ music – a blend of upbeat pop and folk-influenced melodies – was fitting for the sunny summer vibe of her daytime slot and drew in a huge crowd. Rogers rocked a matching tie-dye set of bell bottoms and an oversized T-shirt that formerly belonged to the Grateful Dead’s leading audio engineer, Dan Healy. His daughter Ambrosia Healy, also a “dear friend” of Rogers, loaned her the vintage look for the occasion. It’s undeniable that Rogers is one of the many talented women in the industry who are pushing new sounds and contributing to the evolution of pop that blends electronic production with traditional balladry. 

- Meredith Fuentes 

Bishop Briggs

Image courtesy of Sydney Gawlick/Lollapalooza 2019

Image courtesy of Sydney Gawlick/Lollapalooza 2019

Bishop Briggs performed on the American Eagle stage during the early evening of Day Two. These side stages are usually used for “small artists,” but “small” is not a word that can be used to describe Bishop Briggs. Her voice and stage presence is overwhelming and unbelievable; with every song she performed the crowd felt her passion and strength. Briggs performed songs off her latest album “Church of Scars,” but fans were also able to hear her newly released singles “Tattooed On My Heart” and “Champion.”

- Meredith Fuentes


Janelle Monáe

Image Courtesy of Jaclyn Rivas/Lollapalooza

Image Courtesy of Jaclyn Rivas/Lollapalooza

Janelle Monáe was everything a Lollapalooza headliner should be and more. The only problem is that Monáe was (tragically) not an official headliner. Her intense choreography and stacked setlist – complemented by five wardrobe changes – should’ve scored her the closing slot on the T-Mobile Stage, the biggest of the festival’s eight stages. Monáe’s hour-long set was driven by her contagious joy as well as her politically-charged messages of empowerment. "This is a cold war, do you know what you are fighting for?” she asked the crowd. “Fighting for the rights of women, trans women, LGBTQ.”  

- Montserrat Vazquez-Posada

SATURDAY, DAY 3

Chelsea Cutler

Image courtesy of Grant Hodgeon/Lollapalooza 2019

Image courtesy of Grant Hodgeon/Lollapalooza 2019

If you think you’ve never heard of Chelsea Cutler before, you’re probably wrong. While her own music seems to fly under the radar, she’s all over the radio airwaves as a featured artist on tracks with Kygo, The Chainsmokers, and many others. One of these impressive collaborators, Quinn XCII, even joined her on stage during her set to perform their hit “Flare Guns.” Cutler sported an oversized ACDC shirt and sneakers – a casual look that coupled well with her stage presence. The carefree nature of her performance made you feel like you were simply singing along with your best friend instead of a rising pop star.

- Meredith Fuentes

SUNDAY, DAY 4

Rosalía

Image courtesy of Greg Noire/Lollapalooza 2019

Image courtesy of Greg Noire/Lollapalooza 2019

Spanish singer and songwriter Rosalía has received praise for her collaborations with J Balvin, the Colombian singer who made Lollapalooza history this year on Day Three as the festival’s first Latinx headliner. While she wasn’t able to join him on stage, the Catalonia-native dominated over other artists who performed on the Tito’s Stage throughout the weekend with her effortlessly impressive vocals and unapologetic stage presence. Dressed in mint green from head to toe, she delivered incredible numbers with her team of fierce female dancers. Rosalía brought more than a taste of her flamenco background to Grant Park, closing with the castañuela-driven hit “MALAMENTE.” 

- Montserrat Vazquez-Posada

Kacey Musgraves

Image courtesy of Sydney Gawlik/Lollapalooza 2019

Image courtesy of Sydney Gawlik/Lollapalooza 2019

Kacey Musgraves played a perfect Sunday evening set before headliner Ariana Grande. Her relaxed country style eased the bustling crowd that was eager to see Grande take to the T-Mobile Stage and wrap up the weekend. As the sun set and golden hour was in full swing, Musgraves proved that her 2019 Grammy-winning album “Golden Hour” is one that truly brings listeners together. Her set took place one day after the mass shooting in El Paso, Texas and the same day as the shooting in Dayton, Ohio. Musgraves thanked the crowd at the T-Mobile Stage for their bravery and even had the crowd join her in sending a message of disappointment and frustration to politicians everywhere about gun violence: “Somebody fucking do something.” 

- Meredith Fuentes

Ariana Grande

Image courtesy of Kevin Mazur/Lollapalooza 2019

Image courtesy of Kevin Mazur/Lollapalooza 2019

Ariana Grande exceeded expectations on Sunday night and ended the four-day festival on a perfect note. Following the release of “Boyfriend” the night before, Grande brought out Social House to live debut the track during her headlining set. Her stacked setlist included obvious hits from “thank u, next” and “Sweetener,” as well as throwbacks from earlier albums. Considering every one of her headlining counterparts were male artists, Grande was a refreshing alternative who outshined the festival’s other closers. She made intense choreo look easy as she danced on the catwalk in her recognizable thigh-high boots. Everywhere you looked fans were melting at the sight of her. For an hour and a half, she held the crowd in the palm of her hand. 
Grande proved that women can fill that closing slot just as well as – maybe even better than – boys can. It was disappointing not seeing more female artists as headliners this year, but the performers who made Lollapalooza 2019 what it was were the women who gave it their absolute all whether it was when the gates opened or as the sun set. 

- Montserrat Vazquez-Posada

Steven Norwalk