Oliver launched his solo recording career as "Tree" in 2010. He initially self-released his music but signed with R&S Records in 2011. He eventually found himself on hiatus as he went back to school, studying music technology at California Institute of the Arts.
In November 2016, he returned to music with his television debut performing with Getter on Last Call with Carson Daly.
Shortly after the release of "When I'm Down", Tree signed to Atlantic Records, and a month later graduated from California Institute of the Arts.
Tree often writes, acts and directs in sketch comedy videos, and has worked with companies such as Fuck Jerry, Barstool Sports, and WorldStarHipHop.
In February 2018, Tree released his major label debut EP Alien Boy, along with the double music video for “All That x Alien Boy.” Tree wrote and directed the debut, which took over nine months to create. He spent five months practicing freestyle Monster Truck jumping at the Perris Auto Speedway, and performed all his own stunts in the music video.
Oliver Tree has played major festivals such as Lollapalooza and Outside Lands Music and Arts Festival, and performed as a special guest at Coachella Valley Music and Arts Festival and EDC, most notably at Coachella where he was subsequently named on LA Weekly's "The Best (and Weirdest) Fashion at Coachella" list in 2017.
He was the supporting act on Louis the Child's 2017 Last to Leave Tour (2017) and Skizzy Mars' Are You OK? Tour (2018), and was scheduled to join Lil Dicky and DJ Mustard on the Life Lessons Tour Fall 2018 before it was canceled. Tree is currently touring North America and Europe with Hobo Johnson.
A modified version of his track "Movement" was featured in a 2018 ad for the iPhone X.
On December 7, 2018, Tree released his second music video, "Hurt", a single from his debut album Ugly Is Beautiful. He traveled to Ukraine to film the video, which he wrote and co-directed with Brendan Vaughan, an up-and-coming music video director. In the first week, the music video for "Hurt" reached one million plays while the song received significant radio play.
On April 11, 2019, Tree released his third music video, "Fuck", with the single being released on the same day.
His fourth music video and single, "Miracle Man", was released on June 7, 2019, with the video reaching one million views on the first day of release. On June 12th, he announced that he would give his final tour.