One strange part is there are a lot of Dead Poet's Society references. He was good in the film. I have no issues there, and it's even a decent to good movie (although it becomes a bad Julia Roberts movie later). I enjoy the insurgent campaign of teaching being waged as a fan of the idea of teachers more as motivators who capture interest in a subject and spread it around as an infection to students rather than as instructors who drone on about mechanical processes that we must master. As much as the form of instructing poetry as an insurgent campaign appeals to me as a writer of bad poetry (sometimes), poetry is more complicated as an art to learn to appreciate than just getting the feeling down. There's a flow and lyricism to writing, of all kinds, that doesn't come easily for everyone and is harder to do than just through being "inspiring". The alternative stuff mode of teaching it was awful of course. But art is hard and a complicated subject to portray. Writing is more so because it lacks a visual component. Poetry, because it often relies so much on allusion and imagery can get around this (and because we so rarely engage with modern poets, they're all dead anyway as far as most of us are concerned. People rarely conceive of music as poetry, for some reason, possibly just not enough high quality rap is being consumed on a popular level). Even in the film, the principal measure of artistic expression in the plot is someone wanting to act. Not someone wanting to write poetry or music. That's a curious angle for a film to draw many references back to now; the apparent futility of an entire endeavor of human artistic expression. In spite of its many extolled values, it is treated like a hobby than a passion. That bothers me a bit as a reference point for his career. Whitman should stand on his own. He doesn't need people standing on desks to remind us of that. (Williams made a lot of references to Whitman in his films, probably for that reason).
I'm a little confused why Good Will Hunting isn't getting referenced as much in popular references I see. Maybe it wasn't as drop dead funny (neither was Dead Poets). Maybe it's too close to the subject matter of loss. But it's immediately where I went to. Maybe I just had a stronger connection to this film than that. He won an Oscar, and he was very good in it, and we're probably seeing why. The best performances of many actors/actresses are when they tap their own reality a little more instead of putting on a mask (that's not the "best acting", but the best performances).
The main issue with evaluating Williams as an actor or comedian (beyond the obvious that it limits our evaluation of someone as a complete person to look only at the body of work they produced for public consumption), is this: He would be the person who was probably the funniest person in any room. But it would be hard to translate the joke later to retell it and explain why it was funny. It's like every other bit was an inside joke that spawned from the moment. It might still be funny later. It will make "you" laugh later. But you won't be able to make someone else laugh unless they were there, or shared in it. The secret to that working is that all of us, I think, want to be funny like that. To make it look like a reflex, a reaction, but actually drive the situation and conversation forward and to say something that people look back on and remember. Even if they have a hard time explaining why they do.
And the darker secret to that working is that's exactly why we would want to do it; so nobody will pay that much attention to us for a while. They will laugh, they will enjoy, they will embrace, and they won't look that much harder. Somebody funny doesn't inspire us to ask "what's wrong with them?" versus somebody morose and sullen and even cynical. And yet the funny man often feels no differently, no less alone or confused, than the sullen one. He just provides a better mask that the rest of us can enjoy.