TV Guide: How do you view your time spent on Deadwood?
Boothe: I think I've been incredibly fortunate to be associated with a writer and a creator of the caliber of [series creator] David Milch. What David did with Deadwood was not only groundbreaking, but he also created a kind of new genre. For me, it was almost like doing Shakespeare.

TV Guide: I imagine your Shakespeare background made Milch's dialogue a little easier to handle.
Boothe: Well, it certainly helped. It was like doing Shakespeare in that if you had one word out of place, the dialogue just flat didn't work.

TV Guide: What do you think of Deadwood going out the way it is?
Boothe: I, like everyone, was stunned, because when we left the third season, it wasn't a matter of, "Are we going to do a fourth?" They were negotiating a fifth. And then I got the call from [Milch] that it was all over. I was like, "Are you kidding me?"

TV Guide: Why is Cy Tolliver so clearly tormented?
Boothe: David explained it to me like this: [Cy] was raised in a whorehouse. So you can imagine watching your mother turn tricks and what it does to your thoughts on women. He's a con man, a gambler and a pimp. He's a businessman. And the one thing he can't do is have emotions. But he has feelings for Joanie Stubbs. And he tries to justify them and why she doesn't come back to him. It feeds on his psychosis about his youth and women in general. He has god issues, too. He faced his death and came through it. I think of all the characters — and David told me this — Cy is the only character whose hole card hasn't been revealed yet. I keep waiting for it to happen.

TV Guide: What's the state of the supposed finales?
Boothe: We're planning on doing two two-hour movies this summer. They're talking about [starting production in] June, but I'll tell you, honestly, as much as I hope it happens, I'll believe it when I see it. When a cast splits up, it's hard to bring them back together.

TV Guide: Do you mean that the fate of the movies is in jeopardy?
Boothe: If we don't do it in June, I don't think it'll ever be done, because, look, various people have pilots for other series. I have other commitments, and I know Ian [McShane] has other commitments. That [June] time slot is kind of it. But I think if any show ever deserved at least that much, it's Deadwood.

The two executives said the likelihood of producing movies to wrap up the “Deadwood” saga was about 50-50.

“Our intention is to do them,” Mr. Lombardo said, adding the network doesn’t have holds on most of the actors, who have since moved on to other projects. He said they plan to revisit the movie question with executive producer David Milch at the end of the summer.

...
"David Milch is exhausted," explained HBO exec Michael Lombardo. "We haven't had a conversation with him about scheduling the production of those movies since he's been immersed in 'John From Cincinnati.'"

...

Lombardo and co-president Michael Plepler foxtrotted around the "Deadwood" issue, saying that they intended for the movies to happen but of course they might not, and that it all depended on whether HBO decides to give "John" a second season, to be determined by the end of the summer. But maybe not.

Then came the "ifs": If HBO runs with "John," Milch has to start writing the scripts immediately, which means no "Deadwood." If "John" wipes out, there's still the matter of pulling the actors together, because the channel no longer has holds on them, and ... you know, let's not upset the great one, OK?

This game should be familiar to anyone who been dumped at some point. If HBO intended to go forward with "Deadwood's" movie wrap, they would mention something about ongoing conversations or things in development or any number of phrases designed to inspire hope and patience. None of those crossed anyone's lips this afternoon. ...