‘I Just Want to Bring People Together’: Dermot Kennedy Talks His New Album and Loving the Unpredictability of Playing Live

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It’s the last week of August, and singer-songwriter Dermot Kennedy is gearing up to perform an intimate acoustic set later in the day. The stage? New York City’s Hudson Yards.

This isn’t exactly a typical stop on Kennedy’s tour schedule for the season, but instead to help launch Jameson Irish Whiskey’s Distillery on Tour in New York, an experience that features tastings, along with a special performance from Kennedy, whose second album Sonder drops Nov. 4.

“My relationship with this music is very short-lived,” says Kennedy over the phone earlier that day about the new tracks, which includes the latest single “Kiss Me.” “Like I don’t know it as deeply as I know the other ones. So it almost feels as if me and whoever hears it are going to sort of fall in love with it at the same time. Because some of these songs, I don’t know them for a very long time at all, so that’s what makes the idea of touring them so exciting because I can get to know them in a deeper way.”

Before playing for the crowd in Hudson Yards, Rolling Stone caught up with Kennedy to talk more about teaming up with Jameson for its Busk on Us program, which will help cover the busking fee permits for artists in New York, preparing for his upcoming festival appearances, and connecting with his fans on the road.

Speaking of performing live, you’re set to play Jameson’s Distillery on Tour in New York for the ‘Busk on Us’ program. Are you performing some of those new songs live, and what are your plans for the set?

I’ll do a couple, yeah. I just want to bring people together. I think something that’s been very really beautiful about these busking shows is it just feels very real and very genuine, and there’s a real connection there.

Because so often when you’re on tour, even when you’re playing to 20,000 people, or just 5,000 people, it just, it feels like you kind of run up on stage, do your thing, and leave. And sometimes it feels like you wish you could get a deeper connection with people. Especially in theaters, the room’s so dark, I barely even see people sometimes. That can be a strange feeling, especially when you’re sharing something that’s so meaningful to you, and you know it means a lot to people out there as well, so you just want to be close to them.

So the busking’s a great way to find that connection with people and it’s been really lovely, so I’m going to try to do the same thing this evening.

You started out busking in Dublin, and you’re continuing to do these pop-up performances, the Sonder Street Sessions, for charity. Seeing some of the videos of the performances, they’re outdoors but feel super intimate. What have those shows been like, and which songs are your fans most excited to hear?

One of the things I love about them the most is how kind of unpredictable they are. There are so many variables: A., we don’t know how many people are going to show up. B., I don’t really know what songs I’m playing. And C., you just don’t know how it’s going to go.

Literally, when we played in Philadelphia the other day, two minutes before we started playing I was like in the bar across the street writing the set list down on a piece of paper, and I just kind of love that because I think in music these days, everything is so planned just so much. And set lists are planned. And your lighting is planned. And your album is so planned. And everything is sort of so regimented. Just to be honest, it’s very it’s just fun to not really know what’s going to happen, and it’s nice to be in a position where if you’re playing and someone kind of suggests a certain song, I can actually just play it because it feels like everything is off the cuff, and I like that.

You’re also playing some festivals this fall, including Life is Beautiful and the Ohana Festival. How much of the Sonder Street Session shows and your ‘Acoustic & Intimate’ set will make it into those festival performances? How do you approach those sets?

Yeah, those ones are quite different and to be quite honest, despite how much I love the busking and stuff, I also really love playing like massive shows with a full band and having that full production — that’s my favorite. And I think that when we play a set like that, like a full show, it feels very dynamic in the sense that some moments are really, really up and huge and they feel enormous in terms of their arrangement and the instrumentation. But we also have those moments that are way down and super intimate and very quiet. I’m lucky enough to be able to check all the boxes and get my fix for every thing that I love when I’m playing.

But those shows are a bit bigger, yeah. There’s like about five or six of us on stage, and it just feels like quite a big production, and even though it is this kind of singer-songwriter project, it doesn’t feel like an acoustic show at all.

You started touring with Shawn Mendes earlier this summer. I know he’s a big fan of yours. What was it like playing shows with him, and do you have a favorite track of his?

Yeah, definitely. The shows we did get to do with Shawn — it was hugely valuable just to see a show of that scale to be honest, to see how there’s literally over a hundred people working backstage from early in the morning to get that show up, and just the level of professionalism — it’s just a different level. And also I had no idea how I would feel playing in stadiums to 20,000 people. I didn’t know if that’s something I would like, if I felt like there was intimacy lost or anything like that. But I absolutely loved it, and we loved it as a band, too, so it just worked for us.

And that was very reassuring because I just know that that’s something worth chasing for me now. I really did love that feeling of playing to that many people. And even though it is like 18,000, 20,000, in those rooms it feels like it’s quite intimate. Because the way they’re set up … it just feels like everyone’s attention’s geared towards the stage, like more than a festival so that was very exciting.

In terms of his songs, he’s got so many good ones. But I think, to be honest, the one I was always waiting to hear was “Stitches,” like I think that’s just a ridiculously catchy song. “Monster” is also great. And he played both of them just pared back, just him and acoustic, so it was really cool.