The question—is jazz dead?—has been asked before. In fact, it’s been raised countless times throughout the history of the innovative genre. But when musicians such as Grammy-nominated artist Gerald Clayton and Emmy Award winner Kris Bowers get together, you have your answer. Longtime friends and brothers in beats, rhymes, and life, the pair have created honest and imaginative forms of expression through every note they’ve played.

When we meet for Document, the musicians—both alumni of the Monterey Jazz Festival—are excited to bring their best efforts to the 65th annual event. More than 800 students have been accepted to the Next Generation Jazz Orchestra since its inception in 1971, and this year’s milestone occasion will find Bowers presenting an original piece and Clayton as the artistic director and conductor for The Listening Space.

A longtime mentee and friend of Clayton, Bowers is a well-known pianist and composer who represents a great leap forward in the arena of music supervision and composition. Bowers also has a long history with the festival, having competed at Monterey’s 2004, 2005, and 2006 Next Generation Jazz Festivals. Sharp-eared audiophiles will be familiar with his work, as he’s had his name attached to projects such as Dear White People and When They See Us, and has collaborated with the likes of Jay-Z, Kanye West, and José James.

Ahead of this September’s much-anticipated event, the two sit down with Document to delve into all things jazz, why creativity is their North Star, and how their upcoming appearance at the Monterey Jazz Festival is one not to miss.

Kevin L. Clark: Can each of you share the pivotal moment when you fell in love with jazz music and film? How did that impact you?

Gerald Clayton: I was exposed to music at a pretty young age, and to the community that surrounds the music. I have this memory of being young and seeing a lot of grown men and women telling jokes and laughing and giving each other hugs. [There was] a lot of love surrounding the music. That was part of what attracted me to it. There are records that I’ve fallen in love with along the way. Oscar Peterson was the first artist both me and Kris appreciated. We can name the records that we just wore out, and that we developed that personal relationship with. From then on, your sensors are open to all experiences: other great musicians that you play with, and other great records that those musicians hip you to. It’s this gradual process of taking in good stuff and trying to make sense of it for yourself.

Kris Bowers: Like Gerald said, I think it definitely wasn’t a singular moment. It was a progressive thing. My parents decided before I was born that they wanted me to play piano, just because they’re not musicians. I remember when I decided to go to a conservatory, my parents started to backpedal on their idea of this pianist prodigy. All of a sudden, it was ‘We really want you to be good at piano so you can get a real college scholarship, and get a real education.’ For them, [education] was definitely a serious thing. My dad sat behind me while I practiced every day from the time I was four years old—when I started lessons—until I was 15.

My dad [played] a really integral part in talking to each of my teachers and figuring out what I needed to practice. The big moment that started that progression was my parents putting me in jazz lessons, because I started with classical piano and music theory and I wasn’t super in love with it—or at least with the process and practicing. They put me in jazz because they thought it might be a nice shift for me. Improvisation became a stronger connection to the piano for me. All of a sudden, I realized I could be really angry or sad, and all these emotions that I couldn’t really articulate verbally, and I could go to the piano and play.

I felt like I found my tribe in a really cool way. Which brings us to the festival: I’m excited to walk on those grounds and feel the same nostalgia I felt when I was a kid. I remember being at LACHSA during my freshman year. The senior combo had won, and they were performing at the actual festival. We got to go, and I was hearing so many of my favorite artists in the same space at the same time. I’m excited to re-experience that, for sure.

Kevin: There’s a level of study and introspection that comes with being involved in jazz. You’re both very decorated and have worked in a lot of interesting places. What were some obstacles that you’ve faced in your respective careers that would help to later define your successes?

Gerald: Music is its own challenge. The challenges of trying to figure out what notes to play and what notes not to play, how to leave space and how to make it feel good, and how to make it palatable are huge challenges. In the words of Gregory Hutchinson, ‘Ain’t nobody said it was supposed to be easy.’ Playing music is not just a simple choice of, Ah, I just feel like doing that. I’m gonna do it. You are called to do this. You are inspired to do this. You dedicate and commit yourself to really exploring music through all of the growing pains that come along with it: learning the instrument, and learning whatever language it is that you are inspired by.

A big, challenging period of my life was moving to New York in 2007. Those 10 years of living in the city was a constant feeling of getting my butt kicked. I never stopped getting my butt kicked—I just got used to the feeling of it. That was actually really helpful and instrumental in giving me more courage and flexibility. You can find your way in musical situations that, previously, you might have thought were too wild or too foreign to you.

Kris: I feel the same way. [There are] challenges every single day, and the struggle is what makes it interesting. The constant tension is always exciting when you can look and see how much you’ve progressed. I remember being in high school in Los Angeles, and I started playing at the Mint. Up until that point, I felt like I was just getting my sea legs when it came to playing tunes and interacting with the band. [I began] playing with those guys, and I was just like, ‘Wait, where are we? Where are the changes? What’s going on?’

I started adding notes to the chord changes, and [they] were like, ‘What are you doing? Why are you abstracting those chords? I can’t even hear the melody anymore.’ That was wild to me. Just adding a sixth to this major triad—even though, to me, that feels like the same exact chord—changed the feeling of it. That made me respect that process in a different way.

“I realized I could be really angry or sad, and all these emotions that I couldn’t really articulate verbally, and I could go to the piano and play.”

Kevin: You guys are both at the center of this year’s Monterey Jazz Festival, which is turning 65, and has been considered one of the most legendary experiences for people who love music and jazz culture. First, how does it feel to champion this event for a new generation on what’s considered to be a milestone anniversary? And then, how do you see this juncture impacting your personal and professional development as artists?

Kris: It’s definitely a huge honor to play. I still mentally feel closer to the kids in the Next Gen Orchestra than to the legends that are at this festival. Monterey is so timeless, and it’s great that it stands on its own. Development-wise, I think that because I was commissioned to write this piece, I’m really excited to explore that. I came up with this whole storyline. Usually, whenever I’m writing, l’m really driven by emotion and narrative. The first step is to figure out what I’m trying to say.

Gerald: When you think about yourself and your development, it’s a question of, What tune am I trying to learn? What tune am I trying to write? At the end of that journey, I will have become a bit better from it. In terms of tracking my career, it goes back to these things and has less to do with the award or the gig or whatever it is.

You’re right to point out how classic and giant this Monterey Jazz Festival is to the community. It has always existed in our heads that way because, as Kris said, when we were in high school, we would go and do the competition and see all these great people play. As I’ve returned to be a part of the festival community, I want to thank the folks who actually put the festival on: the people who work year-round to make it happen. It really takes thoughtful and caring, hard work.

Kevin: Gerald, as the director of this year’s Next Generation Jazz Orchestra, you’ll be taking 20 of the most accomplished high school musicians from across the country and lovingly letting them loose on our earholes. What does ‘Director Clayton’ look for in a talent? And with five returning NGJO members, what are you hoping your veteran musicians will pass along to the incoming artists?

Gerald: It’s been a real joy and honor to lead the Next Generation Jazz Orchestra. It is really inspiring to see how the level just keeps rising. The information that cats are dealing with at that phase in their development is very different from what I was dealing with at that age. There is something to be said about this crazy technological boom that we’ve all experienced, where the capacity for information has really grown. First and foremost, I’m just excited and inspired to be around young musicians who are so talented, and who are hungry for this music, and for stories and lessons and experience. That’s really what it’s all about.

For the newcomers and the folks who were here last year, it’s Let’s get together and talk about the music. Let’s play a chart by Thad Jones, Mel Lewis, and then let’s rewind and go back phrase by phrase, and talk about how we can bring out those four bars exactly as they’re meant to be brought out. Are we phrasing that together? How’s our blend? Our intonation? All of the great values that you get from studying the music—but [it’s really about] playing in a big band. It’s a special thing.

Kevin: Kris, can you speak to that as somebody who’s been a part of the orchestra?

Kris: I was really blown away by a lot of the artists who were in that big band, and some of those guys are still playing now. Names like Eddie Barbash, Ben Flocks—these amazing musicians who were in the band when I was in it who were really incredible. It’s such an incredible bridge from the high school music experience, to college and professional settings. It’s always awesome to see how the band continues to develop and grow to find a new sound.

Kevin: How do you both see your individual collaborations with the Monterey Jazz Fest reshaping discussions about Black music? Since jazz is a Black American art form, how do you feel that your collaborations will reshape discussions about Black music in popular culture?

Gerald: I don’t know if I would completely agree with any premise that I’m doing anything that reshapes anything. Anything that talks about the effect of something, I put my hands up. I can’t claim that anything I do will have some kind of impact. I think it’s important. ‘Important’ is another one of those funny words that always needs some unpacking. But I think it’s important that we have opportunities for this community that we know and love: for these great musicians, these great artists to gather, to express themselves, to invite more people to that party. Our responsibility is to get the music out. I feel like exposure is the reason there’s some kind of a big mystery about what the music is, or the fact that we have birthed this incredible language and creation. Yet, the majority of folks growing up here don’t even hear Duke Ellington or Count Basie or Billie Holiday in a major way. Let’s just get it in their ears, and the rest will take care of itself.

“I remember preparing for a competition, and my dad was pushing me, saying, ‘No, what you’re doing isn’t impressive enough.’ I was like, ‘No, I’ve got to play what’s in my heart. I’ve got to sing. I’ve got to play what’s connected to that.’”

Kevin: I want to transition into your friendship. Gerald, you were a mentor to Kris. You’ve seen his development firsthand. What have been your most cherished moments with Kris?

Gerald: Kris has a special quality and spirit within him that I recognized when I first met him. I have enjoyed seeing how that essence has blossomed and been carried throughout his journey. He’s contributed to the music. It really fills me with a sense of pride to see all of the wonderful things he’s doing. It’s all well-deserved. He hasn’t been jaded by any of these experiences. He’s still the same kid who I recognized as that good kid from a good family. It makes me happy. In a way, this is my younger brother right here.

Kevin: Same question for you, Kris.

Kris: I don’t know if I’ve told you about this, Gerald, but one of the big moments for me in my process was a lesson you gave me. I remember you being over at my house and talking about singing while improvising. Until that point, all of my improvisation was kind of regurgitating licks. I would learn these licks, transpose them into all 12 keys, and then assess the chord progression to figure out where I could drop them in. I was treading water until I got to another lick that I really knew. You encouraged me to sing while I played, and talked about the honesty that is inevitable in that process.

I did a lot of competitions in LA when I was growing up, and my dad was very competitive. From the time I was four, he would ask, ‘Are you the best in the class? Are you getting all the solos?’ That’s just never really been who I am in my core. Like Gerald was saying, the reason why I love this music is the communal, conversational, collaborative aspect of it. I remember preparing for a competition, and my dad was pushing me, saying, ‘No, what you’re doing isn’t impressive enough.’ I was like, ‘No, I’ve got to play what’s in my heart. I’ve got to sing. I’ve got to play what’s connected to that.’

That was a frustrating moment for him—accepting this idea that I was just going to trust the process of self-expression, and allow that to develop in its own time, and not necessarily force this facade of what my abilities are. That’s something that’s still such a huge part of the process for me.

Kevin: What does this year’s festival mean for you, as architects of jazz in today’s music scene?

Gerald: It’s another chance for us to invite people to this journey that reminds folks that there is a community of creative expression, artists, and musicians all around you. The way to support that is to go and listen. I don’t care what you think of it. Just come to the gig.

Kris: The beautiful thing about these festivals is that they’re curated in a way where it’s a snapshot of a wealth of diverse music and talent. The exposure is definitely the answer.

The 65th annual Monterey Jazz Festival will take place between September 23 and 25 in Monterey, California. Tickets and more information can be found here.