Q&A with Robyn Ottolini ahead of her Way, Way Back Tour

By Whitney South – Special to SWOMP

Canadian country music’s favourite small-town dreamer turned chart-climber, Robyn Ottolini, is hitting the road — and this time, she’s doing it her way.

The platinum-selling CCMA Award-winning singer-songwriter is more than ready to kick off her headlining Way, Way Back Tour Nov. 6 — which will make its way across Ontario with a stop in Montreal — promising to bring her signature blend of cheeky lyrics, heartfelt storytelling, and unapologetic honesty straight to fans.

This time, as an independent artist, she’s calling all the shots, with the creative freedom to craft songs that feel 100 percent Robyn — encompassing highs and heartbreaks, nostalgic moments, and everything in between. And if you’ve ever seen this incredible woman perform, you know every show is bound to bring plenty of laughs, raw emotion, and more.

We jumped on a call with Robyn to talk everything from pre-tour planning and preparation, to the triumphs and trials of life as an indie, as well as what the future (hopefully) holds for one of the nation’s most electric talents.

WS: Easiest question possible; you have a headlining tour coming up fast — how excited are you to hit the road?

RO: I am so, so excited. Headlining is one of the most fun, but most scary things I think most artists can do because it’s all on your shoulders. But I’m going to have so many really great friends . . . wow, I was going to say friends instead of fans. But really, they are. My fans are my friends too — they’re great and they always show up for me and it’s always a blast. For this tour, I’m hoping everyone is going to see how much work we really put in. The show is very fresh and new from what I’ve done in the past. So, I’m equally as nervous as I am excited.

WS: A lot of performers have different things that they do before a show. What do you do to try and take care of that nervous energy?

RO: “Um, I cry. No, just kidding. I exercise a lot more than I usually do and just eat really healthy for about a month before tour, and while we’re on the road. And then on show days, if I have nerves, I squat a lot — like backstage. That sounds weird. But right before I’m about to go on, you’ll catch me squatting or doing yoga or stretching, just trying to get that nervous energy out of my body. I think it’s okay to be nervous, but I tell myself deep breath, everything’s okay. No one’s gonna die, you know, everything’s fine. If I could bring my dog on stage and just stare at her the whole time, that’d be nice. Or, when I have friends or family members in the crowd, it’s like this instant calm comes over me. I remember my opening night of the Shania Twain tour, that was a huge deal. We were in Halifax, and I came out on stage, and I was scared and just hoped no one would know. All of a sudden, my high school friends — who had flown out for the show — jumped up, like in their row, and everything was immediately okay. It was amazing.

WS: After a huge reaction from fans at the CCMAs in Kelowna (and after teasing us all on TikTok for a bit), you released the track Oh, Canada, co-written by acclaimed songwriters Michael August and Jesse Slack (Owen Riegling’s “Moonshines”), and produced by Grammy-nominated Jordan Schmidt alongside Lenny Pey — can you tell us a little bit about what inspired it?

RO: Yeah, I mean, Canada is my home. I’ve traveled to the UK, and all over the States. I’m in Nashville a lot for writing and recording, but I miss Canada all the time. And it’s the people that make the place — and I love the people in Canada. So, it was just kind of an ode to home. I feel like a lot of people think people in the industry move to America and maybe don’t think about where they came from, and I just wanted to make it very well known that I still love Canada no matter where this journey takes me.

WS: Do you find there’s a certain homecoming when you take the stage here in the Great White North? Do the Canadians welcome you with open arms?

RO: Of course they do. I think they’re open for everyone honestly, when people bring live music up to Canada, everyone is always so stoked. I feel like some of the best country fans are Canadian, and you hear it time and time again. And that’s so special. Like when Morgan Wallen came up and played Boots and Hearts, he said that was probably one of the craziest crowds he’s ever played for. So yeah, they’re very welcoming when I come back, and I think they really appreciate it, too.

WS: Most recently, you dropped your latest single Way Back — the inspiration behind your tour. Can you tell us a little bit about it?

RO: Yeah, Way Back is a song I also wrote with Jesse Slack and Lenny Pey, as well as AJ Gatio, and it’s about that bittersweet, nostalgic feeling when you see an ex . . . in a place where you don’t expect them, and then boom, you’re thinking way back to all these memories. It’s funny because my exes are like, I’m never taking you back — but it’s like, jokes on you, because you take me way back. It’s kind of like a breakup song, but without the sadness. Sometimes it’s a beautiful thing to have those memories, even if you’re not together anymore. That’s how I see the song. I hope that’s how other people see the song, but I also hope they interpret it however they need to.

WS: Nostalgia and memories play a big part in your entire catalog of songs, really. Is that a theme you consciously tend to draw from?

RO: I really do love reflecting on memories. I like looking back into the past and on who I was and what I was doing in general, but you’re so right. In a Small Town is definitely another nostalgic one, and even Oh, Canada is too — I should bring that up in therapy.

WS: Sticking with Way Back, you recently asked your social media followers ‘What memory do you keep going back to, even if they won’t take you back?’ What’s that memory for you?

RO: Such a good question. I feel like I’m a simple person, and the memories I like the most are just back road drivin’, window down, hand out the window, passenger Princess, listening to Old Dominion. But I’m trying to think of like a really beautiful memory — just hanging out with a bunch friends. I’m really sentimental for garage parties for some reason, and I don’t know why. Maybe those are memories. Just like every Friday, you know, meet up at the same place and do it all again. There’s a consistency in that, a safety. I like that.

WS: I have to get greedy here and take a minute to ask you something I’ve always been curious about — and it definitely goes with our theme of memories. In I Want to Tell You Everything, there’s a line that says, ‘I want to tell you everything, every little detail, how I got the scar above my left eye from a kid in middle school.’ Is that a true story? And if so, please spill.

RO: It is a pretty true story. I got a scar on my left eye from a kid I did go to school with. It was elementary school, not middle school, to be fair. If I’m being honest, and I love being honest. I was at their house, and they were playing with a golf club, and the backswing hit me above the eye. Their parents didn’t even call my parents — my mom came to pick me up and I had this huge gaping wound on that boney part right above my eye. So, my mom had to take me to ER, and I had to get a bunch of stitches. She was so confused.

WS: You have no idea how satisfying it is that I was able to ask you that question.

RO: Oh, good. Oh, good. But yeah, that’s my life, you know?

WS: It’s clear you put a lot of thought and detail into your songwriting. Is there anyone you’re listening to right now — any artists out there — that you just can’t get enough of their lyrics or style?

RO: Yeah, it’s funny, because it’s actually a lot of pop artists. But I love Role Model’s lyrics. I love Maisie Peters’ lyrics and Sam Hunt’s lyrics. Oh, and Maren Morris, too.

WS: Tell us, what’s the best thing about moving forward as an independent artist? And what’s the biggest challenge?

RO: The best thing is getting to put out whatever song you want, whenever you want. Right now, it’s the great joy of my life — I’ll write a song that pertains to what I’m going through right at that time, and be able to express exactly how I feel in the moment. That’s the easiest way to be authentic. In the past, I’d write a breakup song, but then it wouldn’t come out for a couple years — when I’d be in a healthy relationship. Things like that.

Something that’s a bit of a challenge is how much you have to depend on the Internet and social media to get your music out there, along with a few phone calls you can make, and just your team around you. So, it can be scary, but I’m here doing everything I can to put out the best music I can. I always say, as long as you’ve got fans, you’ve got a career. And I’ve got the best fans.

WS: Speaking of those fans, is there anything else you want them to know as you kick off the Way, Way Back Tour?

RO: Yes! It’s a fresh set and it’s really fun. We’ve all been working so hard, and I don’t think people will expect the covers that I’m going to do — but maybe they will. Maybe people can read my mind. But really, I’m so excited, the band is amazing, and we’re all really pumped. I can’t wait to see everybody on the road.

Robyn Ottolini’s The Way, Way Back Tour

Nov. 6 Hamilton – Bridgeworks
Nov. 7 Kitchener – The Hub
Nov. 8 Guelph – Sonic Hall
Nov. 9 St Catharines – Warehouse Concert Hall
Nov. 13 Oshawa – The Biltmore Theatre
Nov. 15 Toronto – Lee’s Palace
Nov. 20 Kingston – The Broom Factory
Nov. 21 Ottawa – The 27 Club
Nov. 22 Montreal – Petit Campus