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

“TURR4ZO” Is All You Need To Understand Trueno, The Argentine Rapper Planting His Flag All Around The World [Q&A]

“TURR4ZO” Is All You Need To Understand Trueno, The Argentine Rapper Planting His Flag All Around The World [Q&A]

August 12, 2026 The number “four” is everywhere in Trueno’s world right now, it's shaved into the side of his head and it's in the title of his fourth album TURR4ZO.
Author: Daniela Waizel Rule
How "La Vida Era Más Corta" Turned Milo j's Nostalgia Into One of Latin America's Most Vital Albums [Q&A]

How "La Vida Era Más Corta" Turned Milo j's Nostalgia Into One of Latin America's Most Vital Albums [Q&A]

August 12, 2026 With an album that tackles growing up, enjoying the now and finding our place in the universe, his vulnerable and poetic lyrics show a remarkable analysis of our mortal condition and its growing pains.
Author: Daniela Waizel Rule
Paris Paloma is Embracing her Femininity, and You Should Too [Q&A]

Paris Paloma is Embracing her Femininity, and You Should Too [Q&A]

August 11, 2026 Paris Paloma is emotional, fearless, and embraces every characteristic of what it means to be a woman living in the 21st century.
Author: Isabel Dowell