Christopher Hollyday’s Vanishing Act

The esteemed alto saxophonist decades ago transitioned almost exclusively to teaching—but with a slate of new albums, he is gradually finding his way back into the limelight

Christopher Hollyday

Like thousands of young jazz musicians before and after him, alto saxophonist Christopher Hollyday enrolled at Berklee College of Music to expand his artistic knowledge, learn from seasoned professionals, hone his skills, and chart a path for his future.

Unlike almost any other Berklee student in memory, Hollyday did so after having recorded four albums for a major record label, performing at major clubs and jazz festivals across the nation, and being hailed as one of the most virtuosic young lions of the late 1980s and early ’90s.

Moreover, when the Connecticut-born saxophonist enrolled at Berklee in 1993, his goal was not to lay the groundwork for launching himself into the national limelight. He had already been there as a recording artist and as the leader of his own bands, which included such budding young phenoms as pianists Brad Mehldau and Larry Goldings.

Instead, Hollyday enrolled in order to expand his instrumental palate—on clarinet and flute, specifically—and to prepare himself for a career teaching jazz. That is what he continues to do until this day just north of San Diego, where he moved in 1996 following a brief high school student teaching gig 20 miles outside of Boston in Lexington. His quiet transition to teaching may constitute one of the more notable vanishing acts in jazz. 

“I was able to be at the right place at the right time,” said Hollyday, 49, who was just 18 when he signed a multi-album deal with RCA/Novus and made his debut solo album with such greats as Billy Higgins and Cedar Walton.

“I was able to get that magical ‘1980s triangle,’ which doesn’t exist anymore—a record label supporting you and putting out your music, a booking agent, and a manager,” Hollyday recalled. “And I think I had two publicists back then! The difference is that, when I was doing all those things, I wasn’t doing any teaching. I had a quartet and we were on the road 250 nights in 1991. Doing that, even at 19 and 20, I got a chance to play at colleges and talk to students.

“That’s when I got bit, and realized: ‘I want to teach.’ Not only did I want to teach, I had great jazz professionals telling me: ‘This whole touring and performance thing is up and down. So it’s important you teach, or you’ll wait for the phone to ring for gigs for the rest of your life.’”

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It was sound advice.

Novus dropped Hollyday not long after the release of his fourth album for the label, 1992’s prophetically titled And I’ll Sing Once More. He would not record another album until 2018’s self-produced Telepathy. Without record company support, Hollyday’s touring career evaporated almost as quickly as the young lions phenomenon, which had started in the early 1980s with the ascent of Wynton Marsalis.

Apart from a few club dates that Hollyday was contractually obligated to fulfill, his gig sheet was suddenly empty. Fortuitously, he had already moved from New York to Boston while still touring and recording for Novus. That made it easier for him to subsequently enroll at Berklee and study with the likes of Herb Pomeroy and Phil Wilson. Never mind that some of his instructors and fellow students were stunned to suddenly find Hollyday in their midst as a music education major.

“People thought I was crazy!” he said with a laugh. “I’d just done a bunch of albums, played at the Village Vanguard—which I’d lived around the corner from in Greenwich Village—and toured extensively. And here I was at Berklee, carrying a clarinet, a flute, and all my books. People said: ‘What are you doing here?!’

“But I needed to learn,” he continued. “It’s important for every musician to go to school. I mean, you don’t have to. But you have to learn theory, how to play composed music, theory, how to write charts, and there’s really only one way to do that. You have to have a teacher. There has to be some formal training.

“When I went in to talk to [Berklee’s dean of performance] Matt Marvuglio, he said: ‘Do you want to study with Bill Pierce?’ I replied: ‘No, no, I want to study flute and the clarinet.’ And Matt was like: ‘You’re crazy, but OK.’ That’s when I started working on my doubles and started practicing every day at 7 a.m.  It was so interesting to see great musicians who teach at Berklee, like Bill Pierce and George Garzone, be in every day at 7 a.m., practicing. You know it’s really serious when you have to practice every day at the same time.”

In fact, Berklee was the second music conservatory at which Hollyday studied. In late 1991, after moving to New York from Boston, he had enrolled at the School of Jazz at the New School in Manhattan. He started there the same year as Mehldau and Chris Potter. His New School teachers included Jimmy Cobb, Jim Hall, and Kenny Werner, whom Hollyday later featured on his final Novus album.

But the young saxophonist was on the road so often that his attendance at New School classes became increasingly sporadic. Conversely, Hollyday was so dedicated to his studies at Berklee that he graduated in just three years. To do so, he took 20 credits per semester and attended classes during the summer, in effect making him a year-round student.

Christopher Hollyday

Intriguingly, his start with the saxophone as a kid was decidedly lackadaisical. As Hollyday acknowledged in a 1991 interview with this writer, his main incentive when he started playing alto at age 10 was to “get out of class every day for a half-hour… and that half-hour was really the only time I touched the sax for the first two years.”

That all changed after his older brother played him Charlie Parker’s incandescent 1945 recording of “Ko-Ko.” Mesmerized by what he heard, Hollyday soon stopped taking lessons altogether, a move endorsed by his jazz-loving father. The pre-teen saxophonist began transcribing solos from records and practicing up to eight hours a day in solitude. By the time he was in seventh grade, he was skilled enough to become a member of the high school jazz ensemble. He soon joined his brother’s band and became a fixture at local jam sessions, to which his father happily drove him.

Hollyday chuckled when asked if he has ever encouraged any of his students to stop taking lessons and practice eight hours a day on their own.

“No, but I tell them all about what my story was,” he replied. “I tell them that I didn’t do any math homework, because I did nothing but practice. That won’t fly these days. Now, you have to have good grades to get into music school; you can’t just have ambition. I’m very honest about what my story is and how I did it. And I tell my students how lucky I am to have been given opportunities by great jazz musicians, who put their hands out to me, and said: ‘Here’s some knowledge and wisdom; here’s an opportunity for you. Now, you take that and share it with someone else.’

“They taught me so that I can teach others. I think we all do that, and that’s part of the gratitude and love that music is. Once you do it right, it’s about love, community, friends, colleagues, and respect for the music and musicians that came before you and taught you how to do all this. That holds true whether they met you or you transcribe their music off records. Really, it comes from love. And the whole idea is to give back.”

After moving to the San Diego area in 1996—his wife, Janet, grew up in nearby Garden Grove —Hollyday taught at Orange Glen High School in Escondido for one year. This was followed by a 13-year teaching stint at nearby Valley Center High School, during which time he also taught at several junior colleges. Yet, while he loved teaching—and still does—Hollyday realized that his own playing was suffering because of the long hours required as a public-school teacher.

Needing time to woodshed and build his chops back up, he decided in 2011 to devote himself to teaching privately at Bertrand’s Music, where he now has 30 students a week. He also teaches at San Diego State University, where he earned his master’s in jazz studies, a performance degree, in 2007 and this fall became a part-time faculty member. He credits Bill Yeager, SDSU’s jazz department head, as a key mentor.

“It was invaluable to be able to sit down with Bill every day, to listen to him and watch him teach,” said Hollyday, who applies what he learned from Yeager to his lessons with his own students.

“I enjoy teaching one-on-one,” he added. “That is where I have the most impact with students. That doesn’t mean I won’t go back and teach high school jazz bands again, or that I won’t do a combination of public school and private teaching. But jazz is the one constant for me with all the stuff I’ve been through in my life. All the good stuff, all the bad stuff—everything I did has been about the music, whether it’s the playing, the learning, the teaching, the friends, the business, the living. The music has always been what’s most important.”

Christopher Hollyday

The fundamentals of jazz have remained much the same since Hollyday’s time at Berklee. One of his main goals throughout his teaching career has been to help guide his students by providing those fundamentals. He does so more through suggestion and encouragement than by giving “do it like this” directions.

“Students will come in and play their solos, and part of me wants to tell them how they should play,” Hollyday noted. “But I don’t. Instead, I’ll say: ‘I don’t want to tell you how to play your solo, but you’re not playing the changes.’ Or I’ll ask them: ‘What are you listening to? What do you like?’ Sometimes, they reply: ‘I don’t know.’ And that’s fine, because you have to figure out what you like.”

What has changed since Hollyday’s time at Berklee is technology and the ways in which aspiring young jazz artists access music. Where vinyl albums and CDs used to be the lingua franca, it is now increasingly common that many students don’t actually have—or want—complete albums, just the individual songs they have streamed or downloaded. Hollyday laments that the context in which a song was made, and how it fits into a greater statement as part of an album, has little or no currency for many of his students.

“If they tell me they like Coltrane, I’ll ask them: ‘Well, what album?’ And they’ll have ‘So What,’ but just the song, not the Kind of Blue album by Miles that ‘So What’ is on,” Hollyday said. “I’ll ask if they like the rest of the album, and they’ll tell me: ‘No, I just have that one track.’ That’s a big issue. I tell kids that they must have the whole album and they must catalogue it.

“The other thing is students coming in with material they don’t own. Or they got one song for free, but not the whole album. So, my job is to tell them: ‘You need to get the whole record and listen to all of it. Pick one record and listen to the whole record. Then, pick one tune and just listen to that one tune and one solo, and find that one lick or expression—something you love about that one song—and go learn that and try to catalogue that.’ There are a tremendous number of steps we have to go through to create our own jazz vocabulary that we can use on stage, and it takes a lot of discipline.”

Hollyday is quick to stress that he is not a Luddite who is opposed to technology. He welcomes the immediate access online music offers his students.

“It’s easier now, because we have a lot of tools that are available to students,” he said. “I had to go to used record stores as a kid and hunt for stuff. Now, it’s all available in a few clicks. I love that, because I have it, instantly, to show the students. So, that part I like.”

Yet while he appreciates how easy it is to isolate chord progressions on computers and then loop the progressions to repeat, he discourages his students from playing along with computer programs.

“I use Jamey Aebersold’s Play-A-Longs, which use top musicians simulating live accompaniment,” he said. “The kids all want to use computer programs that play the same rhythms over and over. I don’t see the value of that, even if it’s free. I tell them to play along with the piano solos or the bass solos on records, which is what I used to do.

“Another thing is various students come in with one page of sheet music, which they downloaded for free, and I can’t write on it. Argh! I tell them: ‘You need to buy all of it; it’s only $10!’ There are so many kids who are playing well, because they have access to all those recordings online. But if it’s on YouTube and you’ve already seen it, will you go out and get the live experience of the performer and audience listening, and their spiritual interaction? The electronic options are good in some ways, but you have to go see live music.”

Hollyday also stresses how imperative it is for his students to have musical heroes to learn from and emulate as role models, just as he did—and still does.

“The process of knowing the language, and living it, and falling in love with the music, and finding heroes, and adopting that hero, is a very important thing that we talk about. Studying that hero, and getting to know what you really like, is also very important,” he said.

“So, I try to help my students figure out who they love, and why, or that they don’t even have to have a reason why they love it, just that they do love it,” he continued. “For me, it was hearing Charlie Parker when I was 11 or 12 and how commanding his sound was. I remember Billy Higgins telling my class at the School of Jazz at the New School that it was a ‘sound that swings—listen to that sound.’ Sometimes, my students’ minds are all over the place, so you have to sit them down, and say: ‘Now, we’re going to listen.’ That’s what my father did with me.

“I ask each of my students: ‘Why are you doing this? What is your dream? What do you want to do?’ Then, I tell them: ‘There’s your priority. There’s your focus. You have to be committed and consistent, which means we’ll practice at the same time every day.’ We all have our priorities. And it’s great to talk to young musicians, because I learn from them, too.”

Christopher Hollyday

Hollyday’s switch to private teaching from high schools in 2011 freed him up to begin regularly sitting in at weekly evening jam sessions. He befriended leading trumpeter Gilbert Castellanos, who founded and heads San Diego’s Young Lions Jazz Conservatory. Castellanos encouraged Hollyday and arranged a headlining gig for him at Croce’s West, a now sadly defunct San Diego restaurant and music venue.

No longer required to teach early morning classes, the saxophonist underwent a gradual musical rebirth as a performer. In 2018, he recorded his first new album in 26 years, the self-produced Telepathy, which features Castellanos, rising young piano dynamo Joshua White, bassist Rob Thorsen, and drummer Tyler Kreutel.

In January, Hollyday and the same band will release Dialogue, an even more accomplished album that showcases the leader’s increasingly impressive composing skills as well as his increasingly assured instrumental prowess. Like Telepathy, the new album will be available via his website at christopherhollyday.com.

“The big thing for me now will be getting out of San Diego for gigs and finding work for the band,” he said. “I was blessed when I was younger to have a record company, a manager, an agent and a publicist. Now, it’s me doing all of that, but I’m eager to get on the road with these guys. It will be a whole new learning experience for me.”