If you are interested at all in continental philosophy, I'd say Lyotard is a really good place to start for folks coming from an analytic philosophy or hard sci

If you are interested at all in continental philosophy, I'd say Lyotard is a really good place to start for folks coming from an analytic philosophy or hard science background. He engages with some of the same ideas as the rest of the continental milieu but his writing style is not nearly as dense and allusive as the rest. For more contemporary stuff, Badiou is really interesting. He's, among other things, trying to bridge the gap between analytic and continental philosophy. If you want to dive deeper, I'd try to understand the historical development of contemporary continental philosophy from Kant through German idealism via Hegel. A lot of the stuff that is confusing in continental philosophy is confusing because we tend to teach it without regards to its historical development (I know my continental philosophy class was like this at least).