Owen Wilson was absorbed into Ben Stiller's group of comic actors, and they were basically running things for a few years before the Apatow group took over.
That was also quite helpful!
I do feel like that Luke was always had way too much of a leading man look about him to get him anywhere near the same amount of comedic roles, artificially capping his versatility. I do find it weird that he hasn't shown up in a Wes Anderson film since The Royal Tenenbaums, which for my money is still his finest performance, so who knows.