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 Hailey Picardi Unlocked The Key To Healing in Striking Debut ‘scars to prove it’ [Q&A]

How Hailey Picardi Unlocked The Key To Healing in Striking Debut ‘scars to prove it’ [Q&A]

June 5, 2026 The dichotomy of comfortability and chaos her music thrives within is perfectly captured in hues of deep pink and sunset orange, as she looks out over a vast ocean of intimidating possibilities.
Author: Giselle Libby
pop
EP
Noah Rinker Wants To Bring You Into His World [Q&A]

Noah Rinker Wants To Bring You Into His World [Q&A]

March 19, 2026 Not only has Rinker acquired admirable musical chops and a vibrant and curious personality that further enhances his musical connectedness, he also possesses the artistic vision and keen eye for aesthetic that affords him the luxury of overseeing and driving his creative direction.
Author: Noah Wade
TRXY! Chats Debut Album "Drowning in Bliss", Creative Process, And What's Next [Q&A]

TRXY! Chats Debut Album "Drowning in Bliss", Creative Process, And What's Next [Q&A]

March 19, 2026 If you need distorted melodies draped over languid rough beats, have a love for retro show gaze, then everything about this album is deserving of some playlist shelf space.