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

Genre Bending Gomeroi Artist Rox Lavi pushes boundaries to find his sound.

Genre Bending Gomeroi Artist Rox Lavi pushes boundaries to find his sound.

February 18, 2026 Raised on mum’s singing, Rox Lab has become an artist who moves between rap and indie rock with ease, carrying his story in every line.
Author: Caitlyn Sinclair
Ones To Catch: Governors Ball 2026

Ones To Catch: Governors Ball 2026

February 17, 2026 This year’s Gov Ball lineup truly has something for everyone, but what about those names you haven’t heard of?
Author: Chancey Stefanos
Edgehill is the Indie Valentine We’ve Been Crushing On [Q&A]

Edgehill is the Indie Valentine We’ve Been Crushing On [Q&A]

February 12, 2026 Edgehill have been smarting with great lyrics and deceptively impressive chops the past few years, but on their debut album ‘Ode To The Greenhouse’ they unravel in such a beautiful and purposeful way, its hard not o be a little emotional.
Author: DJ Connor