The oriented skein category OS(z, t) is a ribbon category which underpins the definition of the HOMFLY-PT invariant of an oriented link, in the same way that the Temperley-Lieb category underpins the Jones polynomial. In this article, we develop its representation theory using a highest weight theory approach. This allows us to determine the Grothendieck ring of its additive Karoubi envelope for all possible choices of parameters, including the (already well-known) semisimple case, and all non-semisimple situations. Then we construct a graded lift of OS(z, t) by realizing it as a 2-representation of a Kac-Moody 2-category. We also discuss the degenerate analog of OS(z, t), which is the oriented Brauer category OB(δ).