Imagine a singer-songwriter for whom the people, personalities and the intimate aspects of a person’s daily life are far more meaningful material than romanticism, landscapes, poetics or even politics. While that would accurately describe the often charmingly self-deprecating body of work of Ontario’s Donovan Woods up to this point, you might be pleasantly surprised by the contrasting directions of his upcoming album Both Ways. He turns things way up and turns them way down too.

The album has a much broader appeal than the quiet acoustic and piano tracks that came before. It sees Woods succeeding in taking confident steps toward a broader palette of sounds. While that can be risky for some artists, it pays off on Both Ways for Woods and for the listener. We talked about how an artist pulls that off, about his motivations, inspirations, and his, perhaps, unusually unapologetic love for Drake.

First off, thanks for taking the time to chat and congratulations on the new album. The first Donovan Woods song I ever heard was “My Cousin Has a Grey Cup Ring” from The Hold Up and I was struck by how you, perhaps more than most, are able to show a relatable vulnerability in your songwriting. You don’t have to resort to melodrama. Your wit comes through despite a heartbreaking melody. I think that continues to this day and I’ve always been curious whether that’s a deliberate, conscious effort in your writing or is it just you?

Thank you. Also, this is a good question. That’s something that people say to me — that there’s a vulnerability in the songs that doesn’t seem pretentious or melodramatic, as you put it. I haven’t spent too much time thinking about it because I just want to keep communicating that without trying to, I guess. I think I’m lucky that my voice records well and tends to sound honest. It’s as lucky as being photogenic, I think. You know those people who are actually really photogenic? They look like different people in photographs. I think voices are like that too. I also try to make sure I say the things I actually think, even if they’re selfish sounding. I try not to couch things in poetics, which sometimes feels safer. So, like everything, I think it’s both. I’m kind of trying to, and that’s just what I kind of sound like.

Both Ways feels larger in scope than your previous records. With a few exceptions, you had established yourself on previous records as a guy who makes quiet, emotional, acoustic music and while those elements are still present here, they’re embellished and dialed up to 10. This record goes all in with everything from the juxtaposition of banjo and strings on “Good Lover” to the noise-rock drone on “I Don’t Belong to You”. What’s going on here?

I think what’s going on is that the big songs are making the small songs sound smaller and they in turn are making the big songs sound bigger. There’s a compulsion to push your art further that every artist has. To make it more demonstrative and clear. So on this album I thought maybe I could make the big songs bigger and the small songs even smaller. There’s a kind of tug that you feel as a musician to be moving towards some type of known artistic journey narrative. Like Bob Dylan going electric, or bearded guy going to shack in the woods and making stripped down record. I guess it felt like we were trying to do both in some ways. Though I think, all in all, it’s a more boisterous record than the other ones.

Like you [I presumed], I think Rose Cousins is a fantastic artist who not enough people know about. You can imagine my excitement to hear that you know each other and that she would also appear on a track on the album. That song, “I Ain’t Never Loved No One”, gives your whispered voice a sort of confidence. It sounds more deliberate and intense than similar ‘quiet songs’ you’ve done in the past. Is that because you were performing a duet with Rose? Could you tell us a little about how the idea for that song and how the idea of working with Rose Cousins came to be?

Like YOU, I think Rose is fantastic too. I think she’s one the best songwriters in the country. She writes with an elegance and clarity that is not available to me because it requires an intense work ethic which I do not have. I think maybe my voice sounds confident because I feel like I’m trying to win someone back in that song? That’s what I was imagining anyway. I wrote it with a very talented writer in Nashville named Kylie Sackley. She and I were talking about falling in love when you’re older and you’ve been in love before and how different it is from when you’re young. I knew from the get go that I wanted Rose to sing on the song. I thought she’d just come in and do a lovely harmony, because she’s as good at that as any human on earth, seemingly. But she came into the studio, told me to shut up, went into the booth and sang the whole second verse, the chorus, then dipped into a harmony in the bridge. James Bunton and I smiled and cackled, because we knew it was so good. Her voice contains a sort of open-eyed, invulnerable sadness — a tough sadness. I cannot hear her song “Good Enough” without crying. I think her entrance is my favourite moment on the record. It feels like, finally an actual singer is here.

Let’s talk more about “I Don’t Belong to You” — I don’t remember ever hearing you rock out like that. The drums are aggressive, the vocal style is assertive and then that unexpected winding guitar at the halfway mark made me do a double-take. Is this a Donovan Woods that’s always existed off-record or are you doing something new?

That’s Hawksley Workman playing the drums, and mostly everything else. I went up to his old place in Burk’s Falls and we sat around for two days doing nothing but talking, and then right before I left we wrote and recorded much of that. This side of me has always existed off records, yeah. I just didn’t have the confidence to do it. I don’t think my face looks like it ought to “rock out”. But I don’t care now. It’s a short life, as Drake says. And I think it matches the sentiment of the song. For a long time the melody of that line “I don’t belong to you, you don’t belong to me” was in my head, and then we finally found a context for it.

Is that ‘larger’ sound something we can expect to hear more of on future material or was it more of a one-off idea?

I think there’ll be more of it, but who’s to say.

What about the decision to do this record on your own label, Meant Well? How does the experience differ from a more traditional model of making or releasing a record?

I put the last one out on my own label too. We looked at a few offers, my manager and I, and we just couldn’t really bring ourselves to sign them. The services a label offers are suited for someone who’s looking to set themselves up for explosive growth. I don’t think I’ll ever have that, nor do I want it. We’ve had more success by building an audience in a sustainable way. And, streaming being the way it is, it’s definitely a good idea to own all your own recordings. So, here we are.

Canada has something of an international reputation as a country of notable writers in everything from fiction, to songwriting and even comedy. It’s geography and the people are often credited with inspiring that, but you’re from Toronto which is its most metropolitan and international city. You have also been recognized specifically by your peers as a songwriter of some note and many of your songs seem inspired by your locales at various times in your life. Does being Canadian, and part of that culture play a role in your writing do you think?

I do live in Toronto, but I’m actually from Sarnia (about three hours south) I mean, I don’t know. I love the song “Galveston” but I’ve never been there. I’ve been told that there’s something uniquely Canadian about my writing, but I don’t really know what it is. Again, it’s one of those things that I try not to think about too much. I love Canada, of course. But I love a lot of other places too.

Will Meant Well be championing other artists as well and if so, what type of music or artists will it focus on?

There’s only ever been one artist I’ve considered releasing but it didn’t work out. I’m not sure I have time, but maybe in the future. I’d like to someday, but I’ve met lots of people who work for labels and they seem very stressed out. I try to avoid that.

What other artists are you listening to or excited about these days?

I love Leif Vollebekk. I love The Weather Station. I love The Barr Brothers. I love Jason Isbell. I love the new Kacey Musgraves record. I love Drake in the kind of obsessive way that we all do right now. How has he stayed this impossibly cool, this consistently, for this long? It’s immeasurable but he seems like the most invincible artist of all time, right?

How do you approach your writing? Is it a sit-down in a coffee shop experience? Home studio? Making notes on a plane or something else?

When I’m writing with someone else, it’s kind of like an appointment during the day in a studio. It can be awkward, but it can also be the most wonderful time. It’s like gambling, kind of. When I’m alone, my writing is almost undetectable. I very rarely sit down to do it. I gather up a lot of thoughts and phrases and ideas until I’m ready and then when I finally do pick up a guitar it falls out fairly easily and quickly. But that ‘good songs happen fast’ bullshit is bullshit. It’s really hard and takes a long time. But most of it, for me, is NOT sitting with a guitar and a pen. I’ve never been a sit down and write at least ____ hours per day type of person. It’s so boring. Having an idea is everything. If I don’t have a really good idea, I don’t even bother.

We need to talk about your sense of humor. It would not be an exaggeration to say that your banter between-songs is very much a part of the show. You move smoothly between having an audience laugh along with you right into very moody, touching songs and the back again. If you weren’t so effective at it, it might be jarring. But you’re very funny. Is this an effort to strike a sort of balance or is it completely unconscious?

I was told so many times to stop talking between songs when I was playing the one million shitty gigs I had to play. People still tell me to stop. When I was a kid I saw concerts by people who spoke so well between songs. Fred Eaglesmith, Bruce Cockburn, Jann Arden. I honestly always thought that’s what you were supposed to do — be funny and then play a song. It feels less natural to me to not talk between songs. We have so many songs to play now that I can’t talk quite as much. Or at least that’s what I’ve been telling everyone, but I probably still will.

I count you among a number of Canadian songwriters who for a long time seemed to fly under the mainstream radar despite a considerable talent for songwriting and performance. Craig Cardiff, Rose Cousins as I mentioned, and Petunia. You seem to be emerging in that sense — and deservedly so. What advice would you give other artists on reaching their audience?

I’m just trying really hard to write good songs. That sounds so disingenuous and asshole-ish, I know. But it really is true. There’s so much more to it, of course, but you have to write good songs. It’s the only thing there is. Without good songs, there’s nothing.

Finally, what would you say is something surprising about you that people might not guess knowing you through your music?

I have an embarrassingly large collection of basketball shoes that I am equal parts proud and ashamed of.

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