Oliver Tree

The last time Oliver Tree graced an Austin stage, at ACL Fest 2019, the injured singer whirled around in a gold-painted wheelchair affixed with a microphone stand, wearing a giant foam cowboy hat. That novelty headwear could be seen as seminal imagery for the meme-keen artist, whose latest visual concept is a gratuitously crying cowboy.

“I cry a lot. I’m a very emotional guy. I don’t really cry from being sad as much as I cry from being moved,” says Tree, who says his latest release – a collection of country-themed, pop punk-accented, acoustic guitar-driven sad boy bangers titled Cowboy Tears – addresses a stigma. “In America it’s like, ‘Don’t cry, suck it up, toughen up,’ and I think that’s bullshit.”

That masculinity complex gets lampooned with recent clips of his emotional cowboy face on the frame of a bodybuilder that Tree claims is actually him: “I was upset because I was working out with three different personal trainers, drinking Muscle Milk for breakfast and Muscle Milk for dinner, but I ended up essentially being tricked into taking steroids which, to me, was just not cool.”

As for performing in Texas, where cowboys still exist, Tree says: “I’ve been seeing a lot of cowboys coming to these shows and some of them even have cowboy tears tattoos and customized hats and jackets. The country community has really embraced me.”