Ross James first met Phil Lesh because he answered a Craigslist ad. Brian Lesh, Phil’s younger son, was trying to find a guitarist and pedal steel player for his band. James answered the ad and auditioned at Lesh’s home, although Phil was on the road at the time. James got the gig and later met the Grateful Dead bassist at a rehearsal at the Lesh household. “[Phil] helped me carry my gear into the house and I was walking into the house, and he was like, ‘Watch your step here.” He’s always just been Brian and Grahame’s dad,” James says, calling from his Denver home.

As the quote may suggest, James was not always a Grateful Dead fan. “I didn’t grow up listening to the Dead; I wasn’t that familiar with [their music],” he explains. However, through meeting Lesh, helping with the opening of Terrapin Crossroads and eventually playing in The Terrapin Family Band, James has grown a deep love of the Dead’s music. “It’s like the next chapter of the Great American Songbook,” he says.

James’ love of both the Dead and Bob Dylan (whose songs he often plays with Phil) drove him to create his new project, ‘Gotta Serve Somebody: A Celebration of Dylan & The Dead.’ The project, which features a rotating group of musicians, can be seen at Brooklyn Bowl in New York City on Feb. 25. This iteration will feature Nicki Bluhm, Grahame Lesh, Scott Law and Alex Koford. Tickets to the show are available here.

Below, James discusses the upcoming show, his relationship with Phil Lesh, his love of adjusting setlists on the fly and much more.

I just wanted to start with your upcoming Brooklyn Bowl show, “Ross James’ Gotta Serve Somebody: A Celebration of Dylan & The Dead.” Of course, you have a history of playing with Grateful Dead members and playing Grateful Dead music, but I’m curious about this project. How did this particular concept and show idea come about?

Ever since I started playing with Phil, we always played a lot of Dylan tunes also. There was one gig we did out at the park at Terrapin Crossroads where we did a celebration of the Dylan and the Dead tour that they did. That was kind of when I first had the idea to do something like this. The way that the show flowed with just Dylan tunes and just Dead tunes and no other covers was pretty seamless and interesting and I thought you could expand on it a lot. I’ve always loved the Dylan Rolling Thunder Revue from ‘75, that’s one of my favorite tours and live performances of all time. The energy and spontaneity of that tour combined with the excitement of Europe ‘72, which is my favorite Dead era. It’s sort of what I’m looking to combine here, that fresh, raw energy of both those tours, and weaving from a Dylan tune, to a Dead tune, and back again. It’s a good opportunity to bring some of my favorite musicians together to play it.

Speaking of your favorite musicians, you have a stacked lineup for these shows. How did the lineup come together? Did you have people in mind in advance?

I played with Grahame and Alex in the Terrapin Family Band in and in different bands. I’ve played in Alex’s band, he’s played in my band and all sorts of different stuff over the years. And then I have a trio with Nicki Bluhm and Scott Law, that sort of came about from this trip we do in Europe every year with a group called IGE that brings together all kinds of musicians for two weeks in Europe. We’re doing that again this year in Prague with Peter Rowan and Greensky guys and String Cheese guys and all sorts of people. So, that’s my history with those guys. I’m really just looking for an excuse to play with any and all of them at any opportunity. It’s really cool, Grahame has actually been playing bass lately in a band called Capitol Sun Rays.

I also saw he’s been playing some bass at Terrapin Crossroads gigs. I think there was one recently where Grahame was playing bass for a little bit and then Phil came and replaced him on bass. It was a very cool moment.

He was here in Denver, he stayed with me when he was playing with the Capitol Sun Rays, which is this band with Luther Dickinson and Amy Helm and Birds of Chicago. He sounded great on bass and we were just talking about getting a gig or two live while he’s playing bass because it seemed like it would be a lot of fun. So it’ll be really cool to explore these tunes with him playing bass and Alex on drums. And Scott Law and I have a group called Cosmic Twang. Scott and I play electric guitar together, and it’s pretty close to heaven for me. I love getting to do that with him and Nicki somehow manages to fit so perfectly into all of that. There’s a really good chemistry between all of us and we’ve just played so many shows together. I know that when we get on stage it’s going to be great.

Absolutely. Speaking of the show itself, you mentioned weaving back and forth between Dylan songs and Dead songs. In terms of the setlist, will it be mostly Dylan songs that the Dead played or will you do some songs that they never played themselves?

Kind of a mix. I love the Rolling Thunder stuff, so I tend to start there all the time. But the Dead did “It’s All Over Now, Baby Blue,” right? (double check) Either way, we might play that song, but the version that I love of that song is actually performed by Link Wray, one of my all-time favorite guitar players and songwriters. His version of “Baby Blue” is off this record that’s from the late ‘70s, early ‘80s maybe. It’s not the greatest record, but his version of “Baby Blue” is so cool. It’s about taking songs and playing them the way I want to play them, not trying to replicate or duplicate anything, Just celebrating the music and trying to play it the way that we want to do it.

I assume – considering you guys aren’t a band that’s playing together as that group all the time – that there will be some setlist planning. Will there be room for something like, let’s say, all of a sudden you’re playing “Fire On The Mountain,” when you weren’t planning on it?

That’s something that happens almost every show that I organize. That’s what’s really cool about playing with these guys too, is that they’re all game and everybody is listening. If somebody plays something and we all pick up on it, we can all go there. I’ll have a sketch of what we are going to do, but it’s never carved in stone.

That sounds great. Separately from this show, how did you wind up playing with Phil in the Terrapin Family Band? How has your relationship with Phil grown in your time playing with him?

It’s coming up on ten years ago at this point. Brian, Phil’s younger son, was looking for a guitar player and a pedal steel player for his band. He had just posted an ad on Craigslist in the Bay Area and I had answered it. It didn’t say anything about anything other than that they were looking for a guitar player. I went to audition and it was at Phil’s house, but he was out on the road. I didn’t grow up listening to the Dead, I wasn’t that familiar with it.

At Terrapin Crossroads, there are all of these photographs all over the walls of Phil with everybody. There are pictures of the Jammys and Questlove and Warren and Trey and Bob Dylan and everybody. There are all of these pictures all over the place and the bass player from the band is playing Doug Irwin’s bass. I didn’t recognize what that was and I had never seen anything like it. I was just like, “Where am I right now? What is going on? This doesn’t feel normal at all.”

So, I got the gig with Brian and played with them for a couple years. Phil would also come to our shows and he’d be there at rehearsal. I remember the next time I went to rehearse at the house, I pulled into the driveway and Phil was outside. He helped me carry my gear into the house and I was walking into the house, and he was like, “Watch your step here.” He’s always just been ‘Brian and Grahame’s Dad.’ He’s such a Dad, like, “Watch your step, Son.” He’s the nicest, sweetest guy. Both him and Jill have been really, almost parental figures in my life since then. I’m really lucky to have gotten to know them. But to backtrack, we were playing in Brian’s band, which was called Blue Eyed River at the time, and then Phil would always come to gigs with Barry Sless in Fairfax. They’d just be hanging out and watching. He sat in with us one time at a place called Iron Springs Brewery in Fairfax and that was the first time I played with them. This was the summer before they were going to open Terrapin, they were talking about it.

I was a live sound engineer at the time, and I was saying that it sounded really cool what they were trying to build and if they ever needed any help with anything production-wise down there, I’d love to help. I basically started as a production assistant for Robbie Taylor. If anyone knows Robbie Taylor, they know what an interesting place to start that might be. It was a strange thing: the month before they opened up, they did all these rehearsals and I was helping out with sound. They did these four soft opening shows in the bar before there was ever a stage in the bar or anything. I ended up playing all four of those shows, and it was like, Tim and Nicki Bluhm and Jackie and Bob Weir and Railroad Earth guys. I don’t even know who else, but I didn’t know any of these people and I didn’t know any of the songs they were playing. And I was doing sound at the same time, so I had a mixing board next to me on stage, doing monitors and front of the house.

But that was how it started at Terrapin and then it snowballed into a million different things. I ended up tour managing for Phil for a couple years, like during Fare Thee Well I was his manager. I was helping with anything that needed to happen down there, like playing music, to setting up shows, to booking bands. To answer your question about my view and relationship with Phil, it’s just grown. We’ve been through so much on so many different levels. Sharing those moments on stage with him is an indescribable thing, even on a night when it’s not the best show. There’s always at least one moment that lifts you out of your body with that guy. We’ve also shared the experience of building Terrapin. We were involved in so many of the same meetings and ideas. And going to art museums on the road with him, there’s just all kinds of stuff. He’s a sage and it’s a privilege to get to know somebody like that.

It’s interesting to hear you talk about how you weren’t a Deadhead prior to starting to play this music. I feel like I hear about that sort of thing somewhat often from people who are now parts of the greater Dead scene. For example, when Joe Russo joined Furthur, he just auditioned, having never really heard the Dead’s music, and now of course he’s a big part of the community. Same thing with you: as you said, you started off not even knowing the songs, and now you’re doing a show where part of it is a tribute to your favorite Grateful Dead era.

Joe and I have bonded over the similarities to our winding up in this universe for sure. As an outsider or somebody who hasn’t experienced it, I grew up listening to country music and punk rock. I thought I knew what the Dead was and then you come to find out there’s so much more there than I gave credit. And so many incredible people in and around it. The songs are really incredible, there are so many incredible songs in the catalogue. It’s like the next chapter of the Great American Songbook.

To bring it back to the show, related to your changing relationship with the Dead’s music: was there a moment when you realized you were a big enough fan to have a favorite era? Or, to put it differently, a moment when you realized you loved the music in a deeper way than just enjoying performing the songs?

It’s a little hard for me to pinpoint one moment because it’s all been such a blur and it all kind of happened so fast. The openness to exploration, once I really got that and was comfortable with that, you realize that it’s this never-ending thing. It’s just constantly growing and changing. Never having to play a song the same way is something that has always interested me. And that’s something that I love about the Dylan side of this too because that’s something that he’s done over the years, just reinvented arrangements of tunes. That’s something that resonates with me in a huge way. There have been so many moments where a lyric from one of these tunes that I’ve heard a million times hits me like a freight train. Almost every night playing with Phil there will be a tune that hits me in a new way because of what’s going on in my life or I’m open to receiving it in a different way. That’s something that I appreciate about both the Dead and Dylan, the lyrical content of all these songs. It’s not just about great music, but the stories and the humanity in all the lyrics.

I do have one more question about the venue, Brooklyn Bowl. What is it about the Brooklyn Bowl that fits with this show?

Any chance I can play in one of Pete Shapiro’s rooms, I’m a happy guy. I love working with him, I love the way every one of his venues feels, the way his staff treats you. In terms of the Brooklyn Bowl in particular, I’ve probably played there 20 times at this point; it feels like home. The first time I played there, the neighborhood was not the same as it is now. It’s really cool to see it change. The crowds are always great and the folks that come out to those shows are always so appreciative of the music. What I’m really excited about for this show is that I’ve also got the Mad Alchemy Liquid Light Show as a part of it. Lance, the guy that does that light show, is a dear friend of mine from California and has done a million shows with us. We even got him to do Red Rocks with Phil last year, so I’m really excited to get to bring that San Francisco thing to the Brooklyn Bowl for this show.