Well, this one stopped me in my tracks.  Certainly 17-across, Winner of nine 2011 Tonys, killed me dead.  First of all, I’m embarrassed that I have no idea whatsoever of who won Tony’s, well really, period, (maybe Tommy Tune, but zilch beyond that).  So I’m sitting here staring at the upper part of the puzzle in moderate horror, seeing many open spaces, many “penciled in” spaces, and many clues that mean absolutely nothing to me.

My first strategy in such a situation, and I think it’s a good one, is to be begin by admitting defeat, and going on from there.

Once I admit defeat to this extent, I allow myself to click “check” even just to prove myself wrong, because I really don’t trust my answer.  So I’m chancing being told I’m wrong.  Across Lite  leaves a little red triangle if you’re wrong, something that my prideful puzzling soul is ashamed of.  I know I shouldn’t be ashamed, I’ve been through psychotherapy.   I will be strong.  I will admit defeat, but I will not press Reveal.   I will not turn to Rex Parker, et al., for the answer.

Anyway, you don’t want my life story, you just want a hint:

Bars:  As in legal.  You may remember an old Law and Order where the villain used this term.

Secretary of War under Roosevelt: He was quite famous, though not quite as much as Roosevelt.

Frequenter of Web forums: abbr. :  Notice the abbr.  It doesn’t mean slang.

And finally Winner of nine 2011 Tonys!  :  (So it wasn’t so obscure after all.  Thank …) Don’t get locked into one category of winner, though, when you think about it, who or what could win nine awards?   So is it a two word answer?  Or not?

Not be underdressed?  :  Great answer.  Two words.  (It’s rare, btw, that NYT will go in this direction.   More Brandon Emmett Quigley,

Bit of filming:  Ok there are two closely related four letter words.  They mean close to the same thing.  If you know 4-across, then you’re fine.  Otherwise try to see if you can remember the other meaning and see if it fits better.

I object to 26-down 1998 hit that begins +___, I do believe I’ve failed you.”  crossing 35-down Thomas H. _____ of the silent era!   I dunno, I can make a guess.  Only hint I can say is that each name is unusual, but not particularly strange.

Now back to the bottom right.  Definitely serious trouble for me.  I don’t remember a word for “Legendary creature similar to the Sphinx” though I’m sure I’ll recognize when I get a few more litters….

But here are more unsolvable crosses if you don’t know directly, you can’t easily figure them out…

Soldiering on:

Go downhill fast?:   I think the question mark’s misleading.   Not really a play on words, except if you’re going downhill fast.

There’s a word of what happens here, it’s called a NATTCK.  Remember it.  It”s sure to show up in a future puzle.