When you first connected with him and joined the band, what was the process of learning his catalog like? Did you dig into his discography or listen to certain live shows?

He definitely hooked me up with an archive of live versions of the songs from different iterations of the band. That was the way that I got into it. They sent me a big chunk of songs to learn, basically, to get familiar with the catalog. So I dug into it from the live perspective, and now more recently, I’ve checked out some Phish studio records and been involved with some of the studio records. So it has changed a little bit since then. But my dad also handed me a whole stack of handwritten music, and there’s a lot of stuff that we don’t play anymore that was in there that I got really excited to learn, and then I was like, “Aww, we’re not doing that anymore?” [Laughs.]

Have you tried to bring any of those shows back into rotation?

[Laughs.] Well, I don’t know if it was because I missed it, but we were trying to bring “Cincinnati” back into the repertoire. But it’s constantly changing. It was exciting, it was fun. I just like being challenged by the music, and I think Trey does a really good job of challenging us with what he likes to play every night.

The TAB lineup has shifted a little bit since you joined the band. Especially since James Casey came onboard in 2012, you seem to have grown into a true horn section that has collaborated with a variety of different projects in and out of the Phish world. Did you feel there was a point where the three of you truly clicked?

Jen and I have felt that connection since we met, basically. We were the people that suggested James to Trey, and it didn’t take very long for us to really feel like a unit. The more and more we play, especially the longer tours that we’ve done, it definitely solidifies our connection and we end up finishing each other’s sentences. That makes it really easy to hop into any other situation as a horn section. We can get into gear very quickly because we know each other really well as musicians and as people.

Jen was also quite young when she started playing with Trey. What advice did she give you when you joined TAB?

She’s definitely helped me a lot and still teaches me a lot to this day. She’s shown me the way. A lot of what she teaches by example is that, at a certain point, there are so many brilliant musicians out there, but what makes you stand apart is how easy you are to work with. She’s just such a joy to be around, and so on top of her game logistically, musically and professionally. That’s why she’s so in-demand, and it made me realize that there’s more to having a successful career in the music industry than being a good player. You also have to be a good person, and someone that people can rely on. And also, she taught me not sweat the small stuff—and not go on the Internet. [Laughs.] Because as an 18 year old, I would be incredibly impressionable and definitely took things really hard, when people would criticize or be crude. I think the best advice from her and Trey was just to disengage and not let them get into your psyche at all.

In certain ways, I think people place more emphasis on age difference in the rock and pop worlds than they do in jazz and orchestra settings. Do you feel your time playing in those settings helped you stand next to older musicians more confidently?

That’s a really good point. I’ve always been playing with people older than me, often quite a bit older than me, coming up with my parents being in the Bay Area, and I’ve never felt weird about being friends with people that are twice my age. But I do know that that is a unique thing for certain 18 year olds to feel. But it didn’t bother me—it didn’t even register as weird. And Jen will often say, “You’re just not like most twenty-somethings.”

That’s because I’ve been mostly hanging out with people older than me. I don’t really scream millennial, at least I hope not. I think it helps that I’m used to interacting with different people, and that definitely comes from the jazz world that I grew up in, because I was learning from people older than me. That spurs your growth—I love to play with people that are more experienced than me, even though it might hurt my ego sometimes to be the weakest link. But I think that’s what makes you better. It spurs a lot of improvement, quickly. So I’ve always been excited about those kinds of opportunities to grow.

Speaking of new opportunities, you played with Phish at Madison Square on New Year’s Eve along with the rest of the TAB horns. What were your thoughts on the night?

Nothing could have prepared me for that experience. I’ve been to the Garden before, and actually danced onstage at a Santana concert my dad was playing when I was 12, but I never had performed there, and it’s always been on my bucket list. So to be there on New Year’s Eve, with a sold-out crowd and some of my favorite people in the whole universe, it was really special. The production that they put on for their New Year’s gag was just amazing. It was an incredible thing to witness and to be a part of. So I was pinching myself the whole time. That will probably remain as a highlight of my life. I don’t know what can top that, really.

*You’ve sat in with Phish twice and also contributed to last year’s Big Boat studio album. Musically, did you communicate with Trey differently with Phish versus TAB? *

Oh definitely. I think he’s very reactive to the people he’s playing with, and I think the guys in Phish have such a unique dynamic between each other, and they can go any direction and have been doing it for so long. He definitely adapts to the environment that he’s in—or sets the environment—maybe subconsciously. But I think he does have a different approach in TAB than in Phish. It’s kind of hard to pinpoint, but I think there’s definitely a big difference there. Especially on a New Year’s Eve gig, they have to deliver a show that’s high energy and hits all the right notes, metaphorically speaking, for the audience. Whereas with TAB, I think he likes to bring it down with some of the softer songs that are a little slower and more mellow. I think he also gets to set the tone a little bit more with his solo project. That’s just what I’ve observed.

Shifting back to your work with other people, you mentioned that you were new to the jamband scene when you stared your work with Trey. Now you’ve played with all sorts of people in a lot of different configurations over the years. Who were some of the first people that you really bonded with and started collaborating with once you had your name out there through your work with Trey and through your own band?

There’s a lot of people that I’ve really enjoyed playing with, but people that I really jelled with personally and professionally are the Umphrey’s McGee guys. I had so much fun doing those few gigs with them that I’ve done. More recently, I’ve been doing some work with The Motet. I played with them at Red Rocks this summer and just did a show with them at The Fillmore this past weekend. They’re just such a great group of guys and really putting out incredibly tight, funky music, and it’s super fun to just hop in and be a part of that here and there. Those are two that come to mind that I’ve really enjoyed.

You are also featured on the new album by Big Gigantic, a band that grew out of The Motet. Is The Motet how you got connected with the Big Gigantic world?

No, I knew Dom [Lalli] before that. Dom actually went to my college a long time before I was there, but we were on the same team, so to speak. I met him through Jen when we were out in Denver and realized that we had this connection. We had some of the same teachers at our college and were both jazz musicians that rebelled against the norm. We just love to geek-out about music. He’s such an avid music fan and creates beautiful things. So that’s how we linked up—through Jen and then finding all these commonalities in our stories. I was super excited to get to sing on their Big Gigantic album, which was very much something I wouldn’t have though thought I would be doing three years ago.

Do you feel that your recent work in the hip-hop and electronic realm has influenced your playing?

Yeah, I really have been enjoying the challenge of trying to stay true to myself and bring a certain level of complexity—just keeping my songwriting the way that it’s been, but also kind of reaching out to this new style that obviously people are really relating to right now. I’m trying to put a little something for everyone in my music, because my last couple albums were jazz albums that really only people who enjoy jazz can engage in. So I’ve really enjoyed producing my songs in a different way recently—still trying to stay true to my sound as it’s been my whole musical life, but also exploring other avenues.

It is a cool time to be alive. As a lot of people are aware, music genres are kind of blending into one another. We’re at this day and age where anything is really possible, and for me, not being tethered to one style of music is very liberating.

You have a busy spring between headlining dates, shows with TAB and other collaborations. Are you also working on any studio projects?

I’m really excited for this EP to finally be out. We’ve been working on it for the last couple of years. It’s been about two years since I wrote the songs, and I just took a really long time to realize the project fully. But it’s coming out at the beginning of next month, and then we’re gonna do a New York City release show in March, and Philly as well, and then a San Francisco release show in May. So I’m really looking forward to playing with my band again, and then it’ll be time to figure out what the next step is. I’ve also got a really busy spring with TAB, which will be really nice ‘cause it’s been a long time since we’ve actually had a tour. I am also starting to absorb influences for the next project, back in phase one of the creative process.

Finally, last year you played two shows with you father in TAB when he subbed in while James Casey was on the road with Meghan Trainor. It must have been special to play with him in that setting.

It was such a highlight for me—coming full circle. He was my first teacher, my biggest mentor and also got me that gig in the first place by recommending me to Trey. So, being able to share the stage with him for those two really special shows was like the culmination of all the gratitude and excitement in the world, because he’s my number-one trombone player; he’s always been my role model. To be in a whole different part of the country from where I grew up, sharing the stage with my dad, was a pretty cool moment. It was cool to look over and see him having a great time and beaming about how much fun it is. Jen was like, “Yay! Cressman sandwich!”

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