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Oak's career is one of those stories where the breakthrough is so big it can actually obscure everything that came before it. He was working as a stage actor before Hamilton — building credits, doing the work — but it's the 2015 musical that put him on the map in an undeniable way. Originating not one but two roles in Hamilton (Hercules Mulligan and James Madison) meant he was part of the original cast that essentially rewrote what Broadway could look like, sound like, and mean to a generation of theatergoers (TMDB). The original cast recording went on to reach audiences far beyond anyone who could score a ticket, which means Oak's voice and performances exist in a kind of permanent cultural record. The transition to television came through Station 19, ABC's Grey's Anatomy spin-off, where he took on the role of firefighter Dean Miller (TMDB). It's a role that asked him to carry dramatic weight across long-form serialized storytelling — a very different discipline than live theater, where you get one shot per performance. Station 19 gave him the kind of sustained screen presence that lets an audience actually grow with a character over time, something a film role rarely offers in the same way. Dean Miller became one of the show's more emotionally complex figures across his run on the series. His previous internal profile also references an appearance in A Quiet Place Part II (2021), the John Krasinski-directed thriller — a film that famously demanded its cast convey fear and urgency with almost no dialogue, which, given Oak's theatrical background in physical performance, seems like a natural fit. Whether that role expanded his film profile significantly is an open question, but it points toward a performer who isn't staying in one lane. He's built something rare: a career with genuine credibility in both theater and screen, and he doesn't seem to be done yet.