In our third and final tribute to Oliver Tree, we trace the explosive career that followed his 2016 breakthrough — the bowl cut, the scooter, and the deadpan comedy hiding real emotional depth. From "Welcome to LA" and Alien Boy to the Billboard-charting Ugly Is Beautiful, the viral hit "Life Goes On," a short-lived retirement, and his final self-produced album Love You Madly Hate You Badly, we cover the full arc of an artist who never stopped surprising his audience.
We close with the June 14, 2026 helicopter collision in Rio de Janeiro that ended his life at 32, fourteen days short of his birthday. Rest easy, Oliver.
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This video serves as the final installment of a trilogy documenting the life of artist Oliver Tree. It chronicles his rapid ascent from a niche internet personality to a global music star, detailing his discography and creative evolution before his tragic death in a helicopter collision in Rio de Janeiro on June 14, 2026.
This is the third and final time we'll cover Oliver Tree on this channel.
In the first video, we were there for the news, the helicopter collision above Rio
de Janeiro on June 14th, the world tour that stopped mid-sentence,
the 32 years that ended before they were supposed to.
In the second, we went back to the beginning, the circus parents,
the Harbor High School dubstep scene, the scooter injuries,
the decade of making music for almost nobody.
We left off in 2016 in an apartment closet,
This is where that story picks back up.
Because what happened between 2017 and June 14th, 2026,
was not a slow build or a quiet accumulation.
It was something closer to a controlled explosion,
a career that expanded outward at speed,
an audience that grew by millions while somehow remaining genuinely personal,
and a creative output that never once stopped surprising the people who followed it.
This is Oliver Tree's famous life, the one he built after the closet,
the one that went quiet too soon.
We'll walk through the Atlantic Records years from the beginning,
the Alien Boy EP, the Coachella appearance, the supporting tours,
the delayed debut album he pushed back out of respect for A Country In Mourning.
We'll cover Ugly Is Beautiful and how it hit number one on the rock charts.
We'll talk about Life Goes On and what it became,
Cowboy Tears and the retirement he un-retired himself from,
The fourth and final album, released on April 24th, 2026,
less than two months before the crash.
And then, because this is the last time we'll do this, we'll say goodbye properly.
When Oliver Tree signed to Atlantic Records in late 2016,
he was not simply signing a recording contract.
He was making a creative declaration about exactly what kind of artist he intended to be.
The label had signed a musician.
What arrived was something considerably harder to categorize.
His debut single as Oliver Tree,
Welcome to LA, released May 26th, 2017,
established the aesthetic immediately and without apology.
The bowl cut.
The oversized vintage clothing in the loudest possible colors.
The scooter?
The deadpan comedy layered over genuine melodic craft.
He performed as a special guest at Coachella that year
and was named on LA Weekly's Best and Weirdest Fashion at Coachella list,
a description he would have treated as a compliment.
He served as supporting act on Louis the Child's Last to Leave tour in 2017,
then Skizzy Mars' Are You Okay? tour in 2018,
then toured North America and Europe with Hobo Johnson,
steadily accumulating live audiences who arrived curious about the internet character
and left having experienced something genuinely unexpected.
The Alien Boy EP arrived in February 2018,
anchored by the double music video for All That X Alien Boy.
Nine months in production,
with Oliver performing his own scooter stunts for five of those months.
Hurt, released in December 2018,
was the first clear signal that the comedy was a frame rather than the content.
He had written it about the scooter crash that ended his competitive riding career.
He traveled to Ukraine to film the video himself,
co-directing it with Brendan Vaughn.
It went gold.
Between 2018 and 2019, singles arrived steadily,
Miracle Man,
Cash Machine,
Let Me Down,
Bury Me Alive,
each one adding a different facet to the portrait of an artist who was becoming,
month by month,
someone the music industry had genuinely not seen before.
Oliver Tree announced his debut full-length album in spring 2020 with a release date set.
Then, the murder of George Floyd and the nationwide reckoning that followed
caused him to pause, publicly, explicitly,
stating that he did not believe it was an appropriate time to release his music
when much bigger things deserved the world's attention.
He pushed the date back.
The decision, small in commercial terms,
revealed something about him that the bowl cut and the scooter had always suggested,
but never quite spelled out.
Ugly is Beautiful was released on July 17, 2020.
It debuted at number 14 on the Billboard 200 and number one on the Top Rock Albums chart,
a remarkable commercial performance for an artist whose career had been built
almost entirely through the internet, with minimal traditional radio support.
The album dealt, underneath its maximalist production and genre-blending surface,
with themes of not fitting in, of being treated differently,
of self-acceptance and the gap between how others see you and how you see yourself.
It was autobiographical in the way only the best pop music manages,
specific enough to feel personal,
universal enough that millions of people heard themselves in it.
The deluxe version arrived in May 2021, featuring seven additional tracks,
including Life Goes On.
That song became his largest commercial hit, 3.7 million TikTok uses.
A cultural moment that introduced Oliver Tree to an audience that had never encountered him before.
It was warm where much of his earlier work had been angular,
hopeful where he had often been sardonic.
Life Goes On reached people who did not know they were Oliver Tree fans yet.
It turned out there were a great many of them.
He announced his retirement from music after Ugly is Beautiful.
He meant it at the time, or believed he did, but on June 27, 2021,
he posted to Instagram that he had come out of retirement.
The reason, as best anyone could tell,
was simply that he had more music to make, and he was not done making it.
Cowboy Tears arrived on February 18, 2022,
accompanied by his first full North American headline tour of the same name.
The album expanded his sonic palette further.
Country-adjacent without fully committing,
experimental without losing melody,
absurd without losing heart.
A deluxe edition followed in December 2022.
The title of that deluxe?
Cowboy Tears Drown the World in a Swimming Pool of Sorrow,
which tells you everything you need to know about his relationship to irony and sincerity,
and his refusal, across his entire career, to choose between them.
Alone in a Crowd arrived September 29, 2023.
The title was the most transparent thing he had ever put on a record cover.
A description of the specific condition he had been exploring since the Alien Boy EP,
the feeling of being surrounded by people,
and still somehow outside the frame of ordinary human connection.
He had built a career on making that feeling entertaining, even joyful, to witness.
Alone in a Crowd made it plain.
The audience who received it, over 20 million social media followers,
millions of monthly Spotify listeners,
had always understood, even when the joke was at full volume,
that the person making it was telling them something true.
Love You, Madly Hate You, Badly was released on April 24, 2026,
his fourth studio album, entirely self-produced.
The most personal and direct record he had made,
about the complexity of love and loss,
and the emotional contradiction that had been the animating force
of everything from Hurt to Life Goes On.
He launched the world's first world tour to support it.
A 70-plus date global run taking him through Mexico,
the United States, and South America,
with Asia, New Zealand, South Africa, Europe, and Antarctica still ahead.
Yes, Antarctica.
He had booked a concert in Antarctica, because of course he had.
He played São Paulo.
He posted from Brazil with the same energy and humor
that had defined his online presence for nearly a decade.
On the morning of June 14, 2026,
he boarded a helicopter in the Recreio dos Bandeirantes area of Rio de Janeiro,
bound for the resort town of Angra dos Reis.
The helicopter collided midair with a second aircraft.
All six people on board both helicopters were killed.
Oliver Tri-Nicol was 32 years old, 14 days from his 33rd birthday.
He had European dates in July.
He had the Antarctica show.
There was more music.
There is always more music when someone leaves too early.
Three videos.
One person.
We covered his death.
We covered his childhood.
Now we've covered the years in between.
The rise from a 2017 Coachella sidebar to a billboard number one.
The retirement he walked back in an Instagram post.
The four studio albums.
The 70-plus date world tour that ended in Brazil.
The music is still there.
Life Goes On still streams.
Miss You still moves.
And somewhere on the internet,
the MTV Cribs parody still plays to someone who has never heard of him,
and they watch it once, and then they watch it again.
That's Oliver Tri.
That's the whole thing.
Rest easy, Oliver.