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

How brookelen Found Her Own Light In dark side of the sun [Q&A]

How brookelen Found Her Own Light In dark side of the sun [Q&A]

October 23, 2026 Making 'dark side of the sun' had indie-rock artist brookelen creating in different ways; recording with a live band, shooting stunning visuals with her talented friends, and expanding upon themes that allowed her to face hard truths head on.
Author: Giselle Libby
EP
DJ Suzy Links Up With Her Inner Kira Krash To Create Transformative Debut Album [Q&A]

DJ Suzy Links Up With Her Inner Kira Krash To Create Transformative Debut Album [Q&A]

October 23, 2026 We chatted about the long process of her debut album, what’s changed and what’s stayed true throughout years of growing alongside the friend, foe, and confidant that is 'Kira Krash.'
Author: Giselle Libby
pop
How Whitney Whitney Lost Her Voice And Found A New Sound On ‘1.3’ [Q+A]

How Whitney Whitney Lost Her Voice And Found A New Sound On ‘1.3’ [Q+A]

October 23, 2026 Loss is a part of life, but what do you do when it feels like you’ve lost yourself? How do you figure out where to go from there? If you’re Whitney Whitney, you keep going — and make an excellent new EP, 1.3.
Author: India McCarty
pop
EP
1.3