Canadian Jazz singer Holly Cole takes us behind the music 

Jennifer Stewart: Holly, your interpretations are so emotionally rich and personal. Can you remember the first song you ever sang that made you feel like this is exactly where you should be, this is exactly what you should be doing?

Holly Cole: I can remember that – and it was a long time ago. I was 16, and the song was Body and Soul. I remember this: my brother, who’s a piano player – he was two years older than me, which was a whole lot of years back then – he told me he wanted me to come up on stage and sing with him. He wanted me to do Body and Soul, and I had never performed before. I was so intimidated. I said, “Okay, I’ll do it – but only if I can stand behind you.”

So I stood behind my brother, and it was pretty dark – the lights weren’t on me and stuff – but I sang Body and Soul. And I did feel, at that time – although I was a nervous wreck – I felt that I was at home with that song.

Catherine Clark: So that was age 16. You’ve just released a new album  –  you’ve released many albums! When did you actually realize, though, that you could make a career from singing. Did you know that on stage at 16?

Holly Cole: No, I did not know that on stage at 16 at all. I just knew that I felt at home with music. But it took – it was a number of years later before I achieved some success and knew that. I mean, I guess it was when I was offered a record contract – then I knew it was serious, and it was real and stuff. But that wasn’t until I was in my early 20s.

Jennifer Stewart: Talk to us about how growing up on the East Coast has influenced you as a person and as an artist?

Holly Cole: Well, I’ll tell you – the place I’m sitting in right now is the same place I sat as a little girl. This cottage has been in my family my whole life, and I recently inherited it from my father. I absolutely adore it here. I adore being on the East Coast.

Speaking of my father, I want to share a little story that connects to my new record, Dark Moon. I’ve always been a lover of the moon – it’s been a muse for me for as long as I can remember.

One of my earliest memories is from when I was about four years old. We were living in Halifax, not far from where I am now, and I had the croup – a kind of harsh, barking cough that little kids get. I woke up my parents in the middle of the night, probably around four in the morning. My mom crushed up some aspirin into canned peaches to help me take it, and my dad bundled me up in a pile of blankets, put me on his shoulders, and took me outside for a walk in the night air.

I’ll never forget that moment. I’d never really been outside at four in the morning before. It was so dark – and the only light came from the moon, which seemed to glow over everything. The streets were completely quiet, just my dad’s footsteps on the pavement and the sound of the ocean air. I remember breathing in that damp Halifax night and feeling better, physically and emotionally.

There was something magical about that experience. I felt like I had discovered a secret. I couldn’t understand how the moon could shine so brightly at night, but be invisible during the day. That mystery stuck with me. It made me fall in love with the night – and especially with the moon.

That memory has stayed with me all my life. It’s one of my earliest, and one of the most meaningful.

Jennifer Stewart: Holly, you went through a deeply traumatic experience when you and your band were in Tokyo during the 2011 earthquake and tsunami. In fact, when it was happening, you didn’t think you were going to make it out alive. How did that experience change you as a person and also as an artist?

Holly Cole: That experience… it was awful, obviously. It happened during the earthquake. I was on a different floor of the hotel than the rest of the band, and I didn’t know whether they were alive or not. We were all lying on the floor with our coats over our heads.

The hotel itself – it sounded like an old ship. It was swaying. It was a tall building, and it was moving back and forth like it was going to break. The maids were clinging to the door frames – because if the hotel goes down, that’s your best shot at survival. So they held onto the door frames for dear life.

It was… I mean, it was terrifying. And it just went on and on.

I remember thinking to myself: This might be it. And then I asked myself, What was the best day of your life? I thought about it, and the answer came to me – it was the day I got my horse. I was 13 years old, and that was the happiest day of my life.

I held onto that memory for a while. And in the middle of all that chaos, I felt something unexpected – I felt grateful. That moment changed my life.

I realized I’d been dealt a really good hand. I had beautiful grandparents, wonderful parents. I love my family. I have an amazing band. I’ve had the chance to make the kind of music I want to make, and I’ve found success doing it. That’s incredibly rewarding.

So now, I live with a lot of gratitude. You’re dealt a hand in life, and you can only play the one you’re given – but you do your best with it. And I feel really happy with what I’ve been given.

Catherine Clark: It’s interesting that you were able to take a moment of such abject terror and turn it into a reflection on the good things that have happened to you – and from that, feel gratitude. I mean, I think anytime we escape death, we feel grateful. But there must have been some lingering trauma from that experience. How did it inform the way you live now, and also the music you made afterward?

Holly Cole: Well, there was trauma after that. Even after we got back to Canada, simple things would trigger it – like when my washing machine goes on and shakes the house. I’d have this immediate, knee-jerk reaction of horror… and then realize, Oh, it’s just that.

That kind of thing lingered for a while. But like I said, it also made me more focused on what I have to be happy about – what I’ve been given, yes, but also what I’ve created. And what I still want to create in the future.

That’s something positive I took from a very negative experience. It gave me a deeper sense of purpose and gratitude – and that continues to inform how I live and make music today.

Jennifer Stewart: How has the music industry evolved for women? Has it become more kind? Was it difficult when you started? What are the transitions in the sector that you’ve seen over your career?

Holly Cole: I think it’s changed for the better. It still has a long way to go – it’s still really focused on women’s appearance, and that’s unfortunate. But I do think there are a lot more women in the industry now who are finding great success. And there’s a real variety of women – with different styles, different voices – and I think that enriches everyone. We’re all better for it. So yes, it’s getting better. It’s not there yet, but it’s moving in the right direction.

Catherine Clark: You talked about the focus on appearance, Holly, and I honestly believe that’s something any woman in a forward-facing role feels. Have you ever felt pressure to present yourself – or even your music – a certain way because you’re a woman?

Holly Cole: Yes, I think everyone does, to some extent. That’s just how we grow up – even if you’re not in music, if you’re just a woman in the world, you know that how you appear is considered really important. It shouldn’t be that way, but it is.

In the music industry, or in film and similar spaces, that pressure is even more emphasized. But you know what? I’ve been fortunate. My manager, my record companies – they recognize that I’m not going to go for that kind of pressure, so they don’t really push it. They might kind of wimpily offer some advice, and I’ll just go, “Nah.” So I haven’t had to make many compromises, luckily.

Jennifer Stewart: If you could go back to that time in your life, Holly, when you were just starting to explore jazz and you were new to the sector, and you didn’t quite know what to expect, what piece of advice would you give your younger self?

Holly Cole: The advice I would give is this: get a great band. Surround yourself with people who are like-minded, who are focused, and who share the same musical aesthetic as you. It’s so important.

I see so many young singers working with bands that aren’t really interested in the same things –   it’s unfocused. And what happens is the singer either gets pulled in a direction they’re not comfortable with, or the whole thing just becomes vague.

It’s crucial to have people around you who are on board with your vision and who support you. That kind of alignment is hugely important, especially when you’re starting out.