2002 - 2009
During that time he was doing mostly school plays.
Early 2009
In his high school came a workshop for RADA and he really liked the idea of being an actor.
Late 2009
He applied for a drama school, but didn't get in.
2009 - 2010
He started working different jobs - door to door insurance, call center, retail jobs.
Middle of 2010
He reapplied and got into two drama schools, and even got a DaDAs scholarship. Oliver declined; he was afraid that they would change his acting completely and wouldn't be authentic.
Late 2010
He started applying for short films; he was doing a lot of university graduation films. He did 22 for one year.
2011
He cut the best parts of these short films into a demo reel, got his first agent and started moving forward with his career.
Middle of 2011
He played his first role on the TV show Casualty and as the villain in the movie Community.
2011 - January of 2014
He was playing small roles in TV shows, movies, and short films. Working day and night jobs so that he can go to Los Angeles for the first time. He went there in Janurary, 2014 for a pilot season and by his words it was bad. For six weeks he only got 3 auditions. He returned to London very discouraged.
2015
This year is significant. He got a role in the movie 'Hard Tide'. He said that it gave him a chance for acting; to dive into this character because the previous projects were only small roles. MindGamers also played a big part in his career because it gave him money to go and try again in the USA.
October of 2015
He went back to the USA and had a mini pilot season. Sadly, for one week - nothing. The second week he had only one audition, so he talked with his manager. He advised him to go back to London, but Oliver decided to stay for one more week. During that period, he had many meetings; again, nothing. But on Thursday, he got a call to go for an audition for Into the Badlands.
October of 2015
At the audition, the casting director advised Oliver to refrain from acting and to read the text normally, because he was trying too hard. After finishing the scene, she asked Oliver to meet with the producers. After one hour they came, and talked, and that was it. He goes back to the UK and after 1 week he got a call from AMC that they will fly him out to test the part, and the next day he got the role.
Late 2016
Everything was going great, until he learned that his character would exit the show. Oliver started thinking that his acting was the main reason why they removed him.
Summer of 2017
8 months of nothing. He was doing auditions, but no callback. In the summer, he signed up for acting lessons. During that time he learns something important - instead of trying to be what he think casting directors want, Oliver should focus on authentically presenting himself.
July of 2017
One month later, an audition came in his e-mail, while watching The Hollywood Reporter Roundtables featuring Ryan Murphy, and it was for a new TV show called 9-1-1.
August of 2017
He goes for the audition; everything was okay for now. After that, they called his manager; his audition was great; they wanted Oliver to read to Ryan Murphy and Tim Minear. He goes to read for them; he does 2-3 scenes. They don't say a word to him. While he was grabbing his stuff to leave, they began asking him questions about himself. Then a few days go by and he gets another call; they wanted him to screen test. Not even two hours later, Ryan has said that they are not testing him anymore. Oliver will portray Evan.
If you want more detailed information, you can check the biography page.