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March 2024
Vol. 23, No. 6

Cover Story

CHRISTOPHER HOLLYDAY: Playing It by Ear

by Robert BushJanuary 2019

Photo by John Hancock.


Hollyday’s first album, released in 1989.


Christopher Hollyday at the Monterey Jazz Festival, 1990. Photo by Michael Oletta.


Hollyday with Gilbert Castellanos. Photo by Jon Naugle.


Photo by Manuel Cruces Camberos.


Hollyday with bassist Rob Thorsen. Photo by Jon Naugle.


Christopher Hollyday Bebop Quintet at Dizzy’s. Photo by Barbara Wise.


“He’s just an extraordinary musician. He’s one of those rare players whose instrument just seems like an extension of his body and he can pretty much express whatever he feels. I enjoy and admire his adaptability–he’s such a good on-the-fly player, even when a tune gets called that he’s not familiar with. He’s such an encyclopedia that he can pull it out of nowhere and jump right in. I thoroughly enjoyed making that record [Telepathy] with him; it was great to get him back in the studio and I think it will raise his profile.”

–bassist Rob Thorsen

I remember distinctly the first time alto saxophone master Christopher Hollyday’s name came to my attention. It was a mention in the “jazz bible,” Downbeat magazine around 1990, and he was being hailed as a “young lion,” mentioned in the same breath with such illustrious company as Roy Hargrove, Marcus Roberts, and even Wynton Marsalis.

I didn’t buy his albums, and I missed the chance to catch him at Elario’s soon afterward, but the name continued to bounce around in my skull, so when I met him formally five years ago, playing at a benefit for a jazz writer down on his luck [me], I could honestly say I knew who he was.

He asked me what my favorite Charlie Parker tune was and, without hesitation, I named Bird’s frantic flag-waver “Segment.” Hollyday rushed to the stage where he, Gilbert Castellanos (trumpet), Joshua White (piano), Rob Thorsen (bass), and Duncan Moore (drums) proceeded to burn through that tune with fire and grace.

Hollyday is the kind of cat who must be experienced live. He’s kind of a throwback to an earlier era of jazz, which is funny, because he’s not nearly old enough to have a direct connection with the heyday of Charlie Parker and Dizzy Gillespie–but after I interviewed him–his personal story yielded all of the missing links to provide clarity.

He’s got a huge, joyful sound and you get the impression that if he weren’t so busy playing the horn, he’d have a grin from ear to ear. He’s an unrepentant bebopper whose aesthetic is filled with long twisted lines delivered with a fat, sassy tone with periodic squeals and whinnies for punctuation.

In his “Young Lion” days Hollyday was discovered in his late teens by music producer John Snyder, the guy who managed saxophone legend Ornette Coleman and ran Artists House records. Snyder brought him to the attention of RCA/Novus chief Steve Backer, who drafted the then-20-year-old onto a label that included Henry Threadgill and Muhal Richard Abrams.

Heady stuff for a guy just out of his teens.

But Hollyday’s whole life had been lived as if he was preparing for that moment. I’m getting ahead of myself. Let’s go back, way back, to find out how he got there, what he’s been up to since, and where he hopes the future takes him

Growing up in a jazz family
“For as long as I can remember,” recalls Hollyday, “there was always jazz playing in my house. The very first thing my father would do, when he got home from work as an outdoor power equipment salesman, would be to put on his music. There was always music playing, especially at the dinner table. And the topic of conversation was always jazz history. My dad talked about Dizzy Gillespie, Dave Brubeck, Art Blakey, and Miles Davis. There was always music in the car, and we’d have music playing on his boat when he would take us out fishing. I was surrounded by music long before I started playing. Music was like a second language spoken in our house. We would go to see live music as a family–when I was like seven, my dad got season tickets to the Strand and we saw Basie, Ellington, Buddy Rich and Woody Herman.”

Hollyday’s father served as a towering influence, for all the right reasons.

“He took me to Berklee to see Sonny Rollins in ’78. When I started to get older, we would go out to bars to see music. Plus, I had an older brother, Richard who played trumpet, so there were always three different streams of music going on in my house at all times. There was my father’s music (he was into everything from Dixieland to bebop), my brother’s music (he idolized Clifford Brown and Chet Baker), and once I turned 10 years old you could hear Bird [Charlie Parker, Hollyday’s principal influence] coming out of my room. So we’d all be listening to our own thing. If you walked down the hall, you’d hear one thing collage into the next thing.”

It was the perfect environment to spark a deep love for the music and an atmosphere that also encouraged other pursuits as well.

“I knew the sound of jazz, the stories, the swing long before I took up the instrument in the fourth grade. I adopted my father’s heroes when I was a kid. He would talk about the great writers like Hemingway and he would talk history and philosophy, too. So I had a lot of heroes; he had enormous respect for nature, so we would talk about people like Jacques Cousteau and Carl Sagan. Whenever I would catch a snake, he would insist that I return it exactly where I had found it.”

One gets the idea that young Hollyday might have stood out when compared to other kids his age.

“I didn’t know anything about pop music, but by the time I was in seventh grade, I could sing all of Charlie Parker’s solos. I couldn’t relate at all to pop music until Michael Jackson’s ‘Thriller’ came out–but even then I was more interested in the backing tracks and singing all of the parts more than I was to Jackson himself.”

Given this background I imagined that Hollyday took to the saxophone like a fish to water, but the reality is more nuanced and complex.

“Even though I was really into music as a kid, I didn’t go hog-wild into the saxophone at first. I had a lot of other interests, and the instrument stayed under my bed a lot at first. I was into science and astronomy and the ocean. I was way more into fishing than practicing–would love to fish all day in the summer with my buddies.”

The epiphany that shook his world.
“Then one day my brother put on Charlie Parker’s ‘Koko,’ and it was a spiritual experience for me–a game changer. I knew then that that is what I wanted to do with my life. I went to my dad’s room and I pulled out all of his Charlie Parker records and took them up to my room. Bird just pulled me in, he was like my pied piper. Because I’d grown up in the house I grew up in, I was somehow able to pick up that music by ear and start playing it.”

Hollyday feels that today’s young musicians are being shortchanged on the organic  experience of listening to records with such focus and intensity.

That’s a lost art these days, in my opinion. To learn how to play you should hear it, sing it, play it, and then change it. It gets taught backwards a lot these days in jazz education. Plus all these kids are getting their music from YouTube or iTunes or Spotify. They download one tune at a time and they don’t have the context of holding a record in their hand and seeing who the personnel is and where it was recorded and reading the liner notes. That’s all extremely important information.”

All of a sudden, Hollyday’s other interests began to take a backseat.

“Until I was transformed by Parker’s ‘Koko,’ I thought I’d be a marine biologist or a fisherman because I loved the ocean so much. I’m still fascinated by large cetaceans. I have a ton of books on that.

“I knew my life had changed when I decided to stay home and practice rather than going to the fishing hole with my friends. All of a sudden, I couldn’t understand why I had to attend school rather than practice all day. I used to fake like I was sick anytime I got the chance. Then, my mom would hear me playing and say she was glad I was feeling better and that I had better go to school tomorrow.”

Soon it became an obsession.

“I practiced all day every day. We lived in an apartment and I knew it probably drove my upstairs neighbor crazy. We had an unspoken agreement. I would practice my butt off and listen to music real loud until she stomped three times on her floor–then I would turn everything down or at least try to play real quietly. Sometimes I could go three or four days without her stomping on the floor. This went on for years until we moved out of that apartment.”

The boy with the horn

“From the first moment I played with him, I knew he was an amazing musician. He has a great ear, and he’s very flexible in terms of direction and adaptability. He definitely has his own perspective, but that’s not at the expense of knowing what’s going on around him. He has a very insightful knowledge of the tradition and the players who created the tradition. It’s always a wonderful experience when we can get together either on the stage or in the studio.”

–pianist Joshua White

“I started going to jam sessions when I was in seventh grade. My brother is four and a half years older than me and he was already playing gigs with his own band. One day, his sax player quit and when my dad picked me up from school, he announced that I’d be playing that weekend with my brother’s band, and that I had a week to learn the tunes. He had a lot of gigs; I was still going to jam sessions at the 1369 Club and I was still in the high school band, so I had a lot of irons in the fire.”

The 1369 Club was a happening place at the time, immortalized in the documentary A Place for Jazz, in which you can see a very young Hollyday doing his thing. This was where the young man began to discover his community among the respected elders and heavyweight players in the Cambridge area.

“The older players embraced me. I went with my brother at first and he could already really play, so when he introduced me as a saxophone player, the guy who led the session told me to come back with my horn the next week. You didn’t need to tell me twice! I went back every Tuesday for a long time.”

While Hollyday felt very comfortable developing as a player in the welcoming atmosphere of the 1369 Club, he had some trepidation about sitting in at Wally’s Paradise in Boston.

“I had a hard time working up the courage to sit in there. That was the club where they played the hard tunes, the ones with lots of chord changes and wicked tempos; I was too intimidated for a long time to bring my horn in, but I’d go to listen all the time. Finally when James ‘Saxmo’ Gates got the gig, he convinced me to come on stage, and on that very first night a fight broke out at the bar and one guy had a gun! James was curled up on the floor, trying to protect himself. I was playing ‘I’ll Remember April,’ and he kept signaling for us to go on. I must have taken 60 choruses that night.”

That’s where Hollyday would meet another important mentor, legendary drummer Alan Dawson, who played with Bill Evans, Dexter Gordon, and Sonny Rollins.

“He was a real teacher. He really pushed me to put myself out there, and he would lovingly guide me into the finer details of getting the tempos just right. I started to develop my own voice by listening to a lot of other players. Of course there was Bird, then Sonny Stitt, Jackie McClean and Wayne Shorter. Not just saxophone players either, I listened to Ray Charles and Betty Carter too. After you blend all of those ingredients into your soup, the flavor starts to take on its own character.”

Ups and downs of young lionhood

“Christopher is my equal. I feel strongly about that. We’ll say stuff like ‘Wonder Twins activate’ when we’re playing. We’re coming from the same planet–we have the same vocabulary; we speak the same language. When I found out that he had moved here, I was so excited because I was a huge fan. I tried to get him for a gig at the Athenaeum, but he was in an accident and couldn’t make it. I’ve been urging him on for years to come out and start playing again, and I’m so happy that he has done it. Working with him on his record was the most satisfying session I’ve done in years.”

–Trumpeter Gilbert Castellanos

“I was walking home with one of my best high school friends when I was 16. A car turned the corner and someone yelled something and we yelled back. That was a mistake. They stopped the car and four or five big guys got out and they were going to kick our ass. But one of them recognized me as that kid from TV and he convinced his partners to leave us alone. That was an example of a situation where having a little bit of fame can save your butt.”

Non-ass kickings aside, Hollyday is circumspect about the whole “young lion” experience. “It’s dangerous because it creates expectations, which aren’t necessarily healthy. I hated being used as a marketing device, you know ‘the youngest cat to ever lead a band at the Village Vanguard.’ None of that stuff says anything about the music. The music was the important thing that got lost in all the hype. I’m 48 years old now. Perhaps it has taken me all these years to develop my voice.”

Hollyday made a demo at the age of 17 that featured John Medeski on piano, John Lockwood on bass, and Ron Savage on drums. That demo happened to cross the desk of famed producer John Snyder, and Hollyday was set to make his major-label debut on RCA/Novus.

“He heard my music and he believed in me and before I knew it, I was putting out an album with Wallace Roney on trumpet, Cedar Walton on piano, David Williams on bass, and Billy Higgins on drums! I was both deeply honored and terrified. It was a dream come true but at the same time, it was everything I had been working for since the eighth grade, so it also felt very logical.”

Still, the eager student of jazz history was not unaware of the storied company he was keeping. “I was playing into the same microphone Dexter Gordon used on Doin’ Allright, in the famed studio of Rudy Van Gelder, where Jackie McClean and Herbie Hancock made all of those incredible records.

“Looking back on it, I realize how lucky I was. The record company gave me four albums. You’re supposed to get one. But then the recession of ’93 hit, and Novus folded. Everybody was let go–James Moody, Mulgrew Miller, everybody. The economy had tanked. Movie theaters couldn’t sell tickets. My booking agent [Ted Kurland] couldn’t book a tour for me with enough dates to justify the travel. I was 22 or 23 years old, I didn’t know what a recession was. I just wanted to be able to practice and play.”

Changing careers
Hollyday, on advice from his father, knew he needed to make other plans.

“So, I saw the writing on the wall, and I picked up the phone and called Steve Lipman at the Berklee College of Music, told him I wanted to enroll, and that I needed a full ride. He called me back a few days later and he said yes. I did a double major: arranging and music education and I worked my ass off, getting my degree in three years. I took 24 credits a semester and I went to summer school.

“So when people ask me, ‘what happened to you?’ or ‘where’d you go?’ That’s the answer.”

Hollyday, who had accomplished all of the milestones in his career at such an early age–had done so almost entirely by ear. To say that he was not a strong sight-reader would be an epic understatement.

“I knew I needed to get my reading together. Herb Pomeroy helped me immensely, bringing me along by encouraging me to read everything I could get my hands on while at the same time making sure the arrangers were writing parts that I could actually handle while I caught up.

San Diego
“I met my wife Janet at Berklee, so when I was done with my student teaching at Lexington, I followed her out here. I had visited San Diego before, when I played a week at Elario’s, and I fell in love with the place. So when she suggested moving here, I didn’t need to be talked into it. I already loved this place, so when God put this woman in my life and she said she was from San Diego, it all seemed like it was part of the plan.”

Hollyday didn’t immediately discover the vibrant San Diego jazz scene, but that wasn’t why he came here, anyway.

“When I got here, I didn’t see much of a jazz scene, but it really didn’t matter, because I was going to be a high school teacher. I started at Orange Glen in Escondido and then transferred to Valley Center. And that’s where I spent the next 13 years of my life.”

Hollyday looks back on his time in the public school system with mixed emotions.

“The best part of that experience was working with kids and their parents and a team of teachers and a community. Do you see a pattern here? We have students, we have teachers, we have mentors, and we have community. It’s not that different from what I experienced in music. It happens in high school, it happens in church, it happens in jazz.”

On one hand, Hollyday loved his job. But there was a big sacrifice that took its toll.

“It was wonderful, but spending 70 to 90 hours a week dealing with life as an educator left me with little or no time to practice or play music. My saxophone was disintegrating. We would do a fundraiser every year and sometimes that would be the only time I’d really play it. I realized that if I didn’t start playing this thing, I might lose the ability to function as a musician.”

Hollyday sees the light
Scared by the notion that his musicianship and its accompanying sense of identity was slipping away, Hollyday began to reclaim his life as a performer.

“The ‘comeback’ began slowly. I wasn’t busy during the summers, so I started driving down to the Gilbert Castellanos jam sessions on Wednesday nights. That really felt good. At the same time, I realized I needed to get my master’s degree and, out of nowhere, I got a call from Rick Helzer at San Diego State, just wanting to introduce himself. I mentioned that I was interested in going back to school and he convinced me to come to SDSU. I went back to school for three years and this time I focused on my flute playing, and worked on improving my reading, which I always need to sharpen.”

That’s when Hollyday made another huge life choice.

“I realized that working in the school system was draining me and I really wanted to get back to performing again–to being Christopher Hollyday again. So, I made a leap of faith and switched from being a high school teacher to working with students privately. Once I did that, I found that I had time on my hands–now I could practice and also stay out later at night. Five years ago I realized that there were lots of places to play in San Diego, so all of these elements converged for me and I got excited about the idea of performing again.

“All of a sudden, I realized I had things to say and I wanted to capture and document those things. While it was true that no one was knocking down my door with offers to record, there was no one keeping me from doing it myself. One day I had an epiphany and I knew I had to make another record. I was very fortunate that Gilbert said yes and Joshua and Rob said yes. Joshua recommended Tyler Kreutel and I’m so grateful to have this record out!”

The Telepathy group with Gilbert Castellanos (trumpet) Joshua White (piano), Rob Thosen (bass),s and Tyler Kreutel (drums) will perform at Dizzy’s (1717 Morena Blvd.) on Saturday, January 12 at 8pm.

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