Putting on a show was not a second nature for him, it was his default mode and though friends found it entertaining, it quickly became irritating for the grown ups and the ones enduring it from dawn until night. A real piece of work, he joined the army of "hyperactive" kids with a ton of medication to take. Sure he had issues, but none of them had to do with extra energy that no one knew how to handle. That was his life's problem from the get go, no one ever really know what to do with him. Responsibilities were given to him once he was old enough, but all he wanted was to have fun and entertain others. As he was "told", there was little room to do as he wished but he would need more than some parent rules to stop him from doing what he wanted. Under the influence of his favorite show Saturday Night Live, he joined improv classes at The Second City during school breaks paying his own bill. School had never been his thing and cutting from its time was not an issue, until his parents got word from it. Knowing he was not going to give up on acting and comedy, to prevent it from dropping out a deal was made and Oliver eventually graduated.
Following the end of high school, he remained a couple more weeks in Chicago to study writing while working out some jobs to keep himself fed and with a roof above his head. Appearing in small commercials became his second, unnofficial job too, local commercials of course. Nobody to hunt these down once he would become a nation wide celebrity. Once he felt he was ready, he left home on January '99 and headed to Los Angeles; small parts, extras, more commercials and some part-time at a caller center job kept him busy enough during the day while writing during a big part of the night. Auditioning for Freak and Geeks, he landed with one of the lead roles to his own surprise. He was the right step in the right direction but nothing compared to what would come up eventually.
That part opened up doors to better roles in films and television, which consequently created contacts and new found friendship with people he had admired from his younger years. It was one of this encounters that would give him the push he needed to make the jump to join his favorite show. He never figured he would get the part as he went to audition for SNL, he had never really thought he would even get the nerves to go in the first place. Yet he did, and his work and education was rewarded when he joined the classic comedy sketch weekly show as cast member and writer for 8 years.
Of course when everything goes well, you must ruin it with antics and cliché Hollywood lifestyle addiction. Alcohol started it all, the wrong people opened his eyes to a whole new level of drugs to make his life far more interesting and less dull on the non-working days. Except that's not how it works, and soon he needed it to function. It could have been too late if it was not for a semi-public incident involving him in a shameful state. A wake up call for everyone but also himself, Oliver found his way to rehab with the promise to get his life back on track and focus on his career. It kinda worked, even if there were too many parties with far too much to drink, smoke or snort involved and the following year(s) were much harder for him to handle then he would have though. But he came through and eventually his career didn't suffer any damage for him to bounce back and, somehow, pretend things have always been fine.
To keep himself always employed one way or another, he added a few more roles on his resume by way of producing and pitching show ideas. Because why not? The most fun and possibly therapeutic new adventure he took was voice acting. Something he never thought he would be decent at. But he was, and while it was work it was also a far more relaxed rhythm for him not to put his main task on the back burner. After all, he only wanted steady jobs and the security of it which he got with a line of more or less successful pseudo-comedic roles. On a more personal life, things couldn't be more chaotic, relationships didn't seem to last or get the outcome he hoped and to top everything, one small flind ended with an unexpected child for him to take responsibility for. Sure, there were worse things than to become a father, try co-parenting with someone you barely knew. It was not ideal but it worked. His life worked, so far.
One year after the birth of his son, Oliver realized sticking to SNL was not going to work out with this new side of his life. Luckily, Brooklyn Nine-Nine got picked up for season and while leaving New York and his 8 years job behind was not as easy as it seemed, the change of dynamic and pace was exactly what he needed. Things were at all high, as they tend to be professionally but maybe the pressure of wanting to have it all, the loss of his beloved cat and the pressure of good parenting was too much for the infamous Moo, who found himself relapsing into bad habits at the end of B99's freshman year. 30 days of rehab and he was back on track, this time he was going to make sure he didn't burn himself too much. He'll work less. Or so he believed as he begin to write, plan activities and check out projects when he was not setting up for on set duties. He was trying to be more present at home but being too much of a workaholic proved to be impossible for him not to juggle things. His schedule remains packed, the way he likes it and after his mother's third wedding (the second he witnessed) figured that marriage was not in his schedule.