We Flew to Lollapalooza to Ask Artists the Last Time They Cried

They say laughter is the best medicine but is there anything as cathartic as a good cry? Given that this week marks mental health awareness week and October 10 in particular marks World Mental Health Day, we decided to take that sentiment to heart. This summer we flew to Chicago for Lollapalooza, an annual musical festival held in the heart of the city that brought out the likes of Ariana Grande, Flume, Tame Impala, and a host of up-and-coming artists.

And at this year's Lollapalooza, we asked the artists performing one simple question: when was the last time you cried? Choosing to be as candid as they wished to be, we got to hear from Conan Gray, Scarypoolparty, Alec Benjamin, Social House, Tessa Violet, and so many more on what it was that last tugged on their heartstrings. Because, truth be told, whether or not we find ourselves on festival stages, we all need a good cry now and again.

This year's World Mental Health Day focuses on raising awareness for suicide prevention. You can visit the World Health Organization's page to learn more about this mental health day and previous world mental health days.  

Related Articles

Cavetown is A Fun Adult Who Does Things in New York City [Q&A]

Cavetown is A Fun Adult Who Does Things in New York City [Q&A]

October 9, 2026 Running With Scissors explores a grungier, most tenacious side of Cavetown that had previously minutely explored but never fully committed to. Though constant repetition and light, utilitarian training assist in his ability to push the envelope.
Author: Noah Wade
FLVCKKA Is Blending Hyperpop, Corridos and Other Genres Into Her Own Lane with “Hypercorridos Vol.1”

FLVCKKA Is Blending Hyperpop, Corridos and Other Genres Into Her Own Lane with “Hypercorridos Vol.1”

October 9, 2026 Seeing a woman in a male-dominated genre is encouraging, something FLVCKKA spoke to during our interview: “We can be aggressive and strong, too, and stand our ground just like men who have that same aggression and strength.”
Author: Sarah Ruiz
La Niña Is Learning to Let the Unknown Lead Her Ahead of US Debut [Q&A]

La Niña Is Learning to Let the Unknown Lead Her Ahead of US Debut [Q&A]

October 7, 2026 Rooted in Naples but never confined by it, she has spent nearly a decade turning her experiences, language, and cultural heritage into something entirely her own.
Author: Alessandra Rincon
pop