At a time when the height of popular culture can feel carefully curated, Oliver Tree built his career by taking the path less travelled. Through humour, music, and a unique eye for creativity, he breathed life into his own world while inspiring millions of fans to embrace their quirks along the way. Always funny on purpose, Tree put both his music and iconic bowl haircut on the map. His slapstick-funny persona was a reminder that life lights up differently when you don't always take yourself too seriously.
Once the news of his helicopter accident in Rio de Janeiro, Brazil, broke, many of his supporters took to the internet to express their shock. Others even took it as far as hoping that the news was merely an elaborate prank. Tree was in Brazil for his Love You Madly, Hate You Badly World's First World Tour when the tragic incident involving five other people occurred.
These photos look back on the moments that helped define Tree as of the most unconventional artists of his generation.
1. Promoting 'Voices' with KSI
In 2023, Tree teamed up with KSI to release 'Voices,' an emotional pop-rap track that traversed the heartache of moving on from a breakup. Directed by Tree himself, the music video had the singer's signature eccentricity written all over it.
Days before the song launched, Tree playfully captioned this Instagram photo with 'The two ugliest guys on the internet joined together to drop the worst song you've ever heard today.'
Contrary to his caption, their fandoms would argue that they are pretty great guys and that this so-called 'worst song' is actually a hit that raked in millions of views on YouTube.
2. Double the Humour
If a photo holds a thousand words, this one of Tree in Brazil might be telling a thousand jokes. It's hard to decide whether the funniest thing in this image is his playful double-chin pose or the funny face on his T-shirt.
3. Around the World in Self-Produced Songs
In 2025, Tree took to Instagram to share a carousel of his travels across 7 continents to record his debut album titled 'Love You Madly, Hate You Badly.' The singer wrote and produced each song in his hotel rooms with the objective of returning to the way he used to make music before he was catapulted to stardom. On top of that, in true Tree fashion, each photo had a comedic story to tell.
The Great Wall of China isn't long enough to parallel how many people Oliver Tree has made laugh within the span of his career.
4. Change of Perspective: The Parthenon and the Phenomenon
Two icons in one photo. Standing in front of the Parthenon on the Athenian Acropolis in Greece, Tree muses about the importance of stepping away from the noise in order to see the beauty our planet has to offer. Part of his caption included, 'After logging off, I feel brand new and I can't wait to share my perspective with you.'
5. Smiling at the Sydney Opera House
The same Instagram carousel featured Tree all smiles by the Opera Sydney House. Australia joined the lineup as one of the destinations he chose to record his debut album in.
6. Oliver in Paris
While most people visiting the Eiffel Tower take the dreamiest photos worthy of a Parisian fashion magazine cover, Tree stayed true to his comedic persona by flashing a peace sign and the most unserious face ever.
7. Stone Henge Featuring a Guest Appearance
While Stone Henge still wears the title of archaeology's greatest enigmas, it's no mystery that Tree would not pass up an opportunity to make his photo op there undeniably quirky. His selfie with the English monument features a woman casually strolling by in the background, as Tree strikes another one of his famous funny faces.
8. Will the Real Slim Shady Please Stand Up?
In 2022, Tree posted photos of himself with Post Malone. In the caption he playfully referred to his friend as 'Slim Shady', referencing rapper Eminem.
His caption read: 'I first met slim shady in 2006 when I was recording my album ugly is beautiful. Watching him blossom as the most influential rapper of our generation has been the most inspirational friendship I've ever had'
9. Oliver and GOATs in a Tree
2021 was the year when many might have called Oliver Tree 'the GOAT' (Greatest of All Time). This was most likely due to the fact that his music was making its mark and due to this image with a questionable amount of goats sitting in a tree. Never not funny with heart in his humour, Tree paired the hilarious photo with a soul stirring caption.
His Instagram caption read: 'I've spent the last month exploring the Middle East & Northern Africa while finishing my final album "COWBOY TEARS". This trip has shaped my entire perspective on the world. 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'
10. Oliver Tree Rocks
Five years ago, the singer spent a month in North and Middle East Africa to work on his album titled 'Cowboy Tears.' Clad in Adidas and seated with a majestic landscape as his backdrop, Oliver Tree clearly explored multiple facets of the world, from seas and skies to rocks and trees.
