The voice of David O’Leary, CRB Classical 99.5’s new morning host, might sound familiar. Over the course of a forty-year career on the airwaves, O’Leary has established himself as a mainstay of Greater Boston radio. A private pilot, a voracious reader, an amateur musician and marathoner, O’Leary’s has no shortage of stories to tell. And, unsurprisingly if you’ve listened to one of his broadcasts, he’s no slouch when it comes to conversation. We sat down with CRB Classical’s new morning host to figure out where his love for radio began, what makes him tick, and his hopes for his work with CRB.
You’ve worked in radio for more than 40 years now. How have you found the transition to GBH?
It’s been marvelous. I love being on the radio. I’ve done mornings for many years, so waking up each day for the morning show is nothing new to me. The team at CRB has been incredible. Friends ask me, ‘How do you like the new job?’ And I say, ‘I love it.’ It’s just been amazing in so many ways I hadn’t considered. It’s a great group of people, committed to producing excellent work.
What differences have you found between commercial and public media?
It’s worlds apart. In commercial radio, it’s baked in that you’re beholden to the advertisers and corporate shareholders. They always get the last word. Whereas, public radio is much more focused on, ‘What’s the best way to produce this for the listener? What’s the most high-quality way to perform the job?’ I’ve had a great career in commercial radio, but at this point, it’s nice to be working for the work itself, and not just trying to sell stuff.
Over the course of your career, you’ve adapted to a bunch of different music genres — from rock and adult contemporary to classical. How have you been able to make those transitions in stride?
My job is to connect with listeners — aside from the music — to be relatable and share my life with them a little bit so they see and hear themselves in the show. In some ways, I tend to think it doesn’t matter what the music is if you’re relating to people and connecting with them one-on-one.
Has working at CRB deepened your appreciation for classical music, or opened you up to composers you weren’t familiar with?
A thousand percent. My mom was a graduate of the New England Conservatory of Music, a classically trained pianist. She was a piano teacher, and a choral director at our church for decades. She’s passed now, but when I talk to my siblings about working at CRB, they all say, “She would be so happy you’re there.”
I’ve always had an appreciation for classical music, but I’m connecting with it more deeply and intentionally than ever before. This music we love so much, it’s everywhere. It’s in Bugs Bunny cartoons and a million different pieces of media. It’s withstood the test of time. That’s why we’re still playing these pieces that are, some of them, 300, 400 years old.
What appeals to you about radio?
I like radio because it’s super intimate. You’re in people’s headphones at the gym, you’re in their kitchen while they’re cooking dinner, you’re in their cars as they’re driving to work every day, you’re in their bedrooms when they’re folding laundry; it’s like you’re there with them. When you make that connection with the listener, it really is pretty special.
Have you always wanted to have a career in broadcasting?
Absolutely. I went on a middle school field trip to the local radio station, WGTR 1060, in Natick where I grew up. I was smitten; I fell hard for broadcasting as a 13-year-old kid.
I started hanging around the radio station, and then I got a part-time job painting the place. When I was in high school, I got a job at a rock station in Worcester, WAAF, then I went to another station in Boston, WBCN. There was a TV station called V66, which was a video channel in the 80s, so I was a VJ introducing music videos for as long as the station was on the air. After that, I went to work on the radio at KISS108. I was fortunate in that I’ve been able to stay pretty much in Greater Boston my entire career. I grew up here, so I’m a bit of an anomaly in that I haven’t had to move around a ton for work in broadcasting. But I knew this is what I wanted to do, and where I wanted to do it — I just love it.
Your program starts a little bit earlier now than your previous show. What’s your morning routine look like now?
I go on the air at 5 o’clock on CRB, and I was not quite that early at my last radio station. I will say, and my family will attest to this, that I have embraced the morning lifestyle by going to bed at a decent hour every night. Earlier in my career, I would try to stay up and say “I’ll make up all the sleep” on the weekend. In my old age—maturity, we’ll call it—I’ve become much more cognizant of my need for sleep. Maybe I don’t get a full eight hours every night, but I get a solid seven.
What tricks do you have for maintaining your voice?
I hydrate a great deal, and that keeps my voice in pretty good shape. I try to avoid concerts or ball games — anything where I’m screaming or yelling at the top of my lungs. I’m very attuned to what my voice sounds and feels like. I just try to baby it a little bit, and take care of it.
Is the Boston market unique compared to other places in the country?
It is in the sense that Boston has always been a top-shelf market with great quality programming in just about every format. Other markets — New York City, LA — may be bigger, but it’s just not great radio. This is, writ large, a generalization. But there are some heritage radio stations in Boston that have been admired across the country. In KISS 108’s heyday, everybody was trying to be like them. WBCN, GBH, these stations are known and respected nationwide.
Who would you say has influenced you in your broadcasting career?
That’s a great question. There’s a guy named John Garabedian who is legendary here in the Greater Boston area — but also nationally — with a show called The Open House Party. I know John pretty well, and worked for and with him at a few different radio stations through the years. He’s definitely a mentor and an influence.
The late Dale Dorman is another. He was on the air when I was growing up, but I also had the opportunity to work with him at KISS 108 back in the 80s and 90s. He was just fantastic to work with and for. Anybody over a certain age in Boston knows the name Dale Dorman.
On the programming side, at Magic I worked with Cadillac Jack. People might not know who he is because he wasn’t really on the air, but he was one of the first program directors who really drilled down deep with me to think about storytelling and communicating with efficiency while you’re on the air. I got so much from working with him. When I think about what I bring to my radio broadcast at CRB, I think it’s that kind of storytelling.
Finally, I’ve been able to work with the amazing Cathy Fuller here at CRB over the past few months, exploring the background of so much of the music we play. She’s so knowledgeable about classical music, of course, but she’s absolutely lovely to work with — and one of the biggest Red Sox fans I know!
What’s one word that describes you as a radio host?
Warm, I hope, and relatable.
So, I read you’re a pilot. How did you pick up that hobby?
I was in my early 20s and a friend took me up in a small plane. I was amazed. After that, I wanted to learn to fly. I went to Marlboro Airport, took flying lessons, and got my private pilot’s license.
I wooed my wife in a plane — I’d say, “Let’s fly down to Block Island, or P-Town.” I’ve flown down to Philadelphia to visit one of our daughters who went to school down there. It’s been a tremendous way to spend time when I’m not “on” the air. I’m the president of the Aero Club of New England, which is a nonprofit that offers flying scholarships for young flyers and people who are furthering their aviation training, as well as safety scholarships and education. It’s just nice to be around people who like planes and flying. And it can make for a nice commute.
Dumb question, but can you get radio up there?
Generally it’s not great. You can get satellite radio. But when I’m flying, I’m pretty locked in, listening to air traffic control or the tower, rather than turning the dial to find a song I like.
What other hobbies or interests do you enjoy in your free time?
I’ve run six marathons, including the Chicago Marathon recently with my daughter. I’ve run in support of the American Foundation for Suicide Prevention (AFSP), an organization I’ve been involved with for about 25 years. My cousin died by suicide years ago; mental health and suicide prevention impact a lot of families and communities. I ran the Boston Marathon three times and Chicago twice to fundraise for AFSP, and it’s been an outstanding experience.
What are you reading or watching lately?
I just finished Absolutely on Music: Conversations with Seiji Ozawa by Haruki Murakami. To say it’s about music and the orchestral world would be selling it short. It’s a book about leadership and life, and it’s just a fascinating read. I’ll also read ANYTHING by David Sedaris.
What kind of music do you listen to outside of work?
I play a little guitar and trombone, and I love the blues and rock, as well as showtunes. My wife and I actually met doing theater. I was an actor in the show, she was a stage manager. It was Shakespeare’s Twelfth Night. Thankfully, I was playing a smaller character, so I had all this downtime to chat with the stage manager!
What’s been your favorite aspect of hosting for CRB so far?
Besides the people, it’s amazing to spend so much time with the composers, artists, and music that I’m playing. I played Sibelius’ Finlandia today — I just love that piece. Gershwin’s Rhapsody in Blue is another favorite, and pretty much anything by Mozart. It’s just wonderful music for any part of your day.
What are your hopes for your work with CRB?
Just trying to do substantial, great work is really, really important to me, like everyone else here. I love that this is our goal: to try to serve the listener with companionship through the beauty and power of classical music. I’m just thrilled to be a part of it.
Why is public media important right now?
It’s more important than ever. It seems that public media, television and radio, is one of the only places where you can get high-quality, honest programming.
Listen to Mornings with David O’Leary every weekday morning from 5AM–9:30AM on CRB Classical 99.5, the CRB Classical App, or on classicalwcrb.org.
