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Weir's not worried about Anastasio fitting in. "Trey's well schooled in the style of music we play -- listening intently to what's going on and reacting meaningfully to what other people are playing," he notes. "If there's a key shift or modality shift within a given section, you can hear that and relate, as I say, meaningfully."
Anastasio grew up listening to the Dead. His first show was at the Hartford Civic Center in 1980 when he was 16. "After that, I went to as many shows as I could, sometimes even standing right in front of Jerry, up on the rail, a few feet away from his amplifier," he recalls. "They were utterly one of a kind, carving a completely new path. I owe an enormous debt of gratitude to this band."
While Weir claims to be a Phish phan, he draws a blank when asked his favorite Phish song. "I've been to their shows," he contends. "And I've actually played with them for that matter."
Pete Shapiro, who's producing the shows along with Madison House Presents, helped put the two parties together on several occasions: "When I opened the Capitol Theatre (in Port Chester, N.Y., in 2011), Bob played with Trey. And Trey sat in with Further at Lock'n in 2013. Whenever I can I try to have them do things together."
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Weir, who famously tipped over on stage during a 2013 Further show at The Capitol and this past summer canceled a tour with his band, Ratdog, says he's felling better. "I've got an issue with my shoulder," he acknowledges, "but I've got a way of working with it now."
The big question about these so-called "final shows" is will the Dead ever play together again? "We'll see," Weir says. "I've got some miles left in me, but I'm sure everybody does. I'm the youngest of the guys."
At 67, Weir is a year younger than Kreutzmann, seven years younger than Lesh and four years younger than Hart. Anastasio is 50.
"Bobby and I have been emailing and we're going to get together soon and start practicing, just the two of us," Anastasio adds. "After that the seven of us will hole up in a room and play through the tunes. I can't wait!"
Below, more of our Q&A with Anastasio and Weir:
Exclusive: Grateful Dead to Reunite, Jam With Trey Anastasio for Final Shows
What kind of deliberations went into deciding to do this gig? What were the sorts of things you were weighing, what conversations did you have with Bob, Phil, et al? And what was it that made you say yes?
I got a really heart-warming letter from Phil saying that he and the other three guys had talked about it and hoped I would do it. I didn't hesitate for a second to say yes. It's an absolute honor to be part of this final chapter.
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What's something you've realized about the Grateful Dead and their place in music history since Jerry's death in 1995?
I've realized that it's no coincidence that they named their best album ever American Beauty. Jerry Garcia was a great American master and the Grateful Dead are not just a genuine piece of musical history, but also an important part of American history. This is a band, born right at the beginning of electric rock, that took the American tradition and moved it forward. They really embodied the American concept of freedom, rolling around the country with a ginormous gang of people and the mindset that "you can come if you want, you can leave if you want. We don't know what's going to happen. All we know is we're not looking back." What could be more American?
How excited are you about this 50th anniversary celebration?
I think this is going to be big fun.
What did it take to pull this together? What was the process? When did you start talking about this? And how did this evolve to Chicago?
We only started talking about it somewhere in the neighborhood of six months ago. Then we had to sort through a number of options -- what kind of deal we were going to try to do. Were we going to do a festival-style event or go back to our classic mode of an evening with the band? That's what eventually made the best sense.
Did it take a lot to get everyone on board, everyone in agreement?
Yeeeeeaaaaaah, basically yes… A couple of the guys didn't want to travel that much. Were we going to take it on the road, for instance? All those kinds of considerations all came up. We narrowed it down to: Let's just do it simple and clean.
First off, it's centrally located, so a lot folks can get there. We have a large fan base in the East Coast and the West Coast. We have a large fan base in that area. It just seemed if we were going to do one event like that, we ought to take travel into consideration for our fan base.
For all your experiences traveling around the country with the band, is there anything about Chicago that stands out in your mind?
No place really stands out for me. We had good nights pretty much anywhere you look. That's what I tend to remember. Christ, we've had our share of good nights in Chicago, and I remember them fondly. The decision to do it in Chicago has more to do with, like I said, had more to do with the travel considerations for our fans.
What do you remember when you think back 20 years ago about that last show in Chicago -- July 9, 1995? What's your memory of that?
What I remember was standing there after the show under the fireworks and bidding Jerry goodbye for the last time -- you know, for what turned out to be the last time. We had done so many nights at Soldier Field that I can't really pull that show. I remember people sitting from time to time, but I don't remember if it was that night or another night. It doesn't really matter.
Do you recall playing with Trey in the past?
Yeah, but not enough actually. We had fun the times that we played together. It just hasn't happened all that much. This is an opportunity for us to explore some of the promise that we discovered back then.
So the meeting of the Dead and Phish -- do you see this as significant? Do you view the bands as similar or very different?
Well, the M.O. is the same. You state the theme and take it for a little walk in the woods. And they're good at that. Beyond that, the comparison is just apples and oranges. They have their flavor, we have ours. It will probably get a little of Phish's flavor, though I haven't had a chance to talk to Trey yet. Any minute now we'll be on the phone. My guess he's going to try to intuit what it is that's most Dead-esque rather than interpret it Phish-style. I'm open to either approach.
Of all the guitar players who've come in the wake of Jerry -- in Further, Phil & Friends, Ratdog and The Dead -- who's your favorite?
[Long pause] That's sort of an unfair question, because I haven't played with enough of them. The guy I zero in on in my endeavors is Steve Kimock. He's one hell of a guitar player and one hell of a musician.
I'm hearing that this might be it for the Dead -- these three shows and that's kind of it. Is there any truth to that?
[Pause] We'll see. I've got some miles left in me, but I'm sure everybody does.
What do you expect the scene to be like in Chicago? Do you expect that big Grateful Dead scene coming out for perhaps the last time?
Well, I hope it's not the last time. But I would expect that that whole scene has evolved to what it is over the years. I don't expect it to change overnight.
I think this is a great opportunity for us to do a little musical exploration, so here we go.
Correction: A previous version of this article mistakenly stated that Weir was older than Kreutzmann. He is, in fact, a year younger.