Oliver Tree is one of music's biggest enigmas. It's hard to know when he's being truthful, and when he's pulling the leg of an unsuspecting interviewer - though, as he sings on Playing With Fire, a song off his country-themed new album Cowboy Tears, "But baby, don't call me liar/Watch me while I'm playin' with fire".
He's as funny as he is musically talented, which is one of the reasons he's become a fan-favourite. If you're not following him on social media, then you're missing out - in recent times, he's fully embraced TikTok, where he now has 12.3 million followers and counting. To celebrate the release of Cowboy Tears, we've taken a look at Oliver's evolution as an artist over the years, and how he's swapped the bowl cut for a cowboy hat (and a blonde bowlcut mullet). Who doesn't love a style icon?
The early days of Oliver Tree
Oliver's first EP, Demons, was released back in 2013 while he was simply called Tree, but it was his 2018 EP, Alien Boy, which showed the world what he was capable of when he set his mind to it. To accompany the project, Oliver spent five months practicing monster truck jumps, set on performing his own stunts for the video (despite the inherent danger), with the stunts featuring in the music video for All That X Alien Boy.
Throughout the video, Oliver switches between riding a scooter and driving in a monster truck, all the while looking impossibly cool. Please, do not try these stunts at home. Fans will also notice that at the end of the clip, Oliver rides a horse while wearing a cowboy hat - potentially foreshadowing what was to come years later. We get the feeling that if you tell Oliver Tree he can't do something, then he's going to prove you wrong.
Realising Ugly Is Beautiful
The release of his debut album, Ugly Is Beautiful, saw his antics ramp up. From partnering with FuckJerry on Instagram to building the world's biggest scooter (a running theme for Oliver), the man with arguably the world's most famous bowl cut had everyone's attention. He'd put his all into promoting Ugly Is Beautiful, and it paid off, charting in the US, Australia, New Zealand and more.
It helped that the album featured tracks like Alien Boy and Hurt, with the latter delving into his relationship with fame, through the lens of an injury that resulted from a scooter competition he attended when he was 18 (or at least, so Oliver says. It's hard to take anything he says at face-value, given how much of a joker he is). Ugly Is Beautiful built on Oliver's previous releases, incorporating elements of pop, electronic music, rock and hip-hop. For all the joking around, Ugly Is Beautiful proved that his music is every bit as entertaining as his antics, if not more so.
The end of Oliver Tree's Ugly Is Beautiful era brought the deluxe album, Ugly Is Beautiful: Shorter, Thicker & Uglier. The highlight of the deluxe album is Life Goes On, one of Oliver's most popular tracks - and one fans were hoping would be on the original project. It's a bouncy, electro-pop track that explores the intersection of being a musician and continuing to live his life. At the end of the day, Life Goes On, Oliver asserts.
The track would spawn multiple remixes, including one released at the end of 2021, featuring Ski Mask The Slump God and Trippie Redd. The Lyrical Lemonade video for the track features Oliver deep in his Cowboy Tears era, so he's rocking the "Bowlett" (half bowl cut, half mullet) - and it's a great bridge between his eras.
Crying Cowboy Tears
Oliver first teased the release of Cowboy Tears all the way back in June 2021, posting on Instagram that his retirement was over before it had begun. Fans were given an insight into Oliver's thoughts on the album when he spoke to Audacy in late 2021, having previously mentioned that he was going down a more country route.
It was a world away from his previous releases, but as he explained, "This is the only thing I listen to. I only listen to the new stuff. I'm like, this is the greatest album I've ever heard in my entire life. If you guys don't want it, I could care less because I'm listening to this thing 24/7." He was backing himself in all the way.
Putting all the gags and memes aside, Cowboy Tears feels like a lifting of the veil. Yes, Oliver might be dressed as a cowboy, but he's serious on songs like Cigarettes, where Oliver laments his nicotine addiction (he teased the track on Instagram and wrote "I quit cigarettes one year ago today") and California, where he explores his love for the city. The electronic pop sounds that drove Ugly Is Beautiful forward have been replaced by swaying acoustic guitar, giving Oliver's voice the chance to shine more than ever - and he rises to the occasion vocally.
Cowboy Tears is a more vulnerable album than Ugly Is Beautiful, which was the aim for Oliver. In November 2021, Oliver took to Instagram to give fans an update on the album, writing, "Life is not about the destination, but the journey. The two year journey creating this album has made me mature and evolve into the artist and (most importantly) the human I’ve always wanted to be.
"I can’t wait for y’all to hear what I’ve been pouring my soul into all this time. To the old fans, thank you for sticking around, and to the new fans, thank you for joining us on this beautiful journey." Being a fan of Oliver Tree can be a confusing experience at times (after all, he did announce he was retiring back in 2020), but at the heart of everything is a musician who 100% believes in themself and their art. On Cowboy Tears, Oliver has shifted genres, but the things that fans love about him are still present - his vocals, his lyricism, and yes, his antics all featuring heavily in this era.
READ MORE: 6 Times Oliver Tree Was A Total Memelord
Only Oliver knows whether this is his last release, as he's claimed or if there's still more music to come. Either way, Cowboy Tears marks an evolution for Oliver. It's one that many might not have seen coming, but will nonetheless enjoy. If you'd asked fans to predict after Ugly Is Beautiful what the cover of Oliver's next album would look like, we're not sure many would have picked a country-themed look - but hey, who doesn't love a cowboy that's not afraid to show emotion?