Meet the trucker hat-wearing musical sensation whose delicate lyrics and distinctive, sound has amassed millions of streams worldwide.

James Gillespie for Rollacoaster SS20 hat
James Gillespie for Rollacoaster SS20 hat

Taken from the Spring/Summer 2020 issue of Rollacoaster. Order your copy now.

Gillespie has shared stages with Pink, Facetimed Elton John and had his intimately wrought anthems draw fans from every corner of the globe. It’s no surprise then the artist is pegged to be one of 2020’s most exciting artists, a sort of modern-day troubadour whose colourful life has led him all over the world and – from the sounds of it – into all sorts of trouble. With his debut album Safe out now, we caught up with a rambunctious Gillespie to talk about keeping it moving, making music and a particularly cryptic encounter with a Spanish monastery…

You’ve led quite a nomadic existence, where does that wanderlust come from?
I have no idea where it came from to be honest. I left the country really young and one thing just lead to another. There was always an excuse to leave the country and move to another one. If I’m honest – I don’t think I liked the idea of putting roots down.

When you were in your teens, something happened, and you had to flee to a Spanish monastery. What happened exactly?
Haha, not much I can say here. I made some questionable decisions when I was younger! A friend knew about this monastery in the mountains for €8 a night. It was kind of cool. Lights out after 7pm type [of] stuff.

I heard that while you were in France you convinced promoters you were a big deal in Scotland to get on the line-up. Would you describe yourself as a bit of a hustler?
How do you know all this stuff? Yeah. I just knew I wouldn’t be taken seriously unless I have some kind of proof that I was good enough to perform. So I lied. And it worked. Big time. It was how I got my first gigs, how I got did my first recording and probably the only reason I’m signed now.

Operator Records booked you into a studio for a day and you came out with 38 songs! How did you manage that?
I had written A LOT while I was travelling. Then after signing the first thing they did was ask to hear my demos… which I didn’t have. So, they put me in a studio and asked me to record whatever I had written… and God knows how many hours later I had 38 songs done!

You performed “Don’t Let Me Get Me” onstage alongside Pink herself. How was that experience for you?
Where do I start? We played about 4 shows together, each as crazy as the next. She’s just the most talented, amazing person. It just oozes out of her. So relaxed, so professional and so fucking lovely.

What’s next for you? Can you tell us about the new single?
“Someday Sundays” is an uplifting tune about escaping all the shit that’s going on around you and just having a great time. We get too caught up sometimes. You need to get away every now and again. It features a friend of mine Nattie [Natassja Shiner], who is the singer from Fickle Friends – another awesome woman and crazy talent. I was super lucky that she was into the song.

Gillespie’s debut album Safe is out now.

James Gillespie for Rollacoaster SS20 standing
James Gillespie for Rollacoaster SS20 standing
Meara Kallista Morse
Anastasia Busch
James Coward
Hannah Brooke at Gary Represents
Federica Barletta
Production assistant
Penny Nakan