The first time Justin Rutledge told Gord Downie he was going to make an album of Tragically Hip cover songs, it was via an email. “He wrote me back, ‘Sounds like career suicide to me,’” Rutledge say, laughing. “I thought that was perfect.”

The album in question is Daredevil, which consists of 10 stripped-down and atmospheric Hip covers. The emphasis is on the Kingston band’s ‘90s output, from Road Apples to Phantom Power.

“I wanted to focus on the years when I got into the band, when I was 16 or 17” says Rutledge, on the phone from New York. “That golden period of Tragically Hip.”

Starting with a long list of 25 songs, Rutledge carefully curated the song selection down to 10 and brought in guests like Brendan Canning, Jenn Grant, Mary Margaret O’Hara and Andy Maize to help him realize his vision.

“I’m not looking to make any money off this,” he says. “This idea was strictly respect. I wanted to pay homage to these wonderful people who gave us all these great songs.”

Below, Rutledge takes us through each track.

‘Looking For A Place to Happen’

"It’s a really interesting song. Of course I’m a huge fan of Gord’s lyrics, but there’s this really Bukowski-esque ne’er do well aspect, these strange characters. I see them sitting at a bar in limbo or the afterlife. You got Jacques Cartier putting his coat on the bed, stuff like that. I chose that song because it’s really a strange little poem. When we produced it, I wanted to create this ethereal environment that was almost creepy."

‘Springtime in Vienna’

"I’ve always had a thing for Vienna, and maybe it stemmed from that song. It’s this amazing chorus, 'We live to survive our paradoxes,' it’s anthemic and it’s joyous and it’s cryptic, and I’ve always had a penchant for that song. I really wanted to make this one a little more folky, and then there is this big choir at the end that really elevates that chorus. Gord belts it out in the original, but we almost made it more plaintive, more gospel."

‘Thugs’

"This song was very difficult to work out. It was the one song where we just didn’t know what to do. I thought this would be an easy project but it ended up being one of the more difficult projects I’ve worked on. And 'Thugs,' it’s a very small song, two verses, two choruses and this outro, but I really wanted to make it more driving and dark, but musical. It’s one of the most difficult to do though because it’s like, only the Hip can do these songs. Hopefully it worked out."

‘Escape is at Hand for the Travellin' Man’

"It’s always been one of my favourite Hip tunes. It’s actually this really sad song about a suicide. It's a real heartbreak of a song on the chorus: 'I guess I’m too slow, I guess I’m too slow.' So I really wanted the lyrics at the forefront of this because it’s a really powerful song and a great story. Gord at his best storytelling."

‘Grace, Too’

"It's such a creepy song and it’s always confused me. As Canadians, how does a song like that, and I mean this with all respect, but it’s a dark song, it’s very creepy, it’s really enigmatic, but it’s one of the biggest Canadian songs of all time. Another difficult one to do. The version we do is almost like a duet, with myself and Julie Fader, who sings with me on the whole album. It’s a conversational song between a man and woman who are in this strange dark place. Having Julie helped me understand that more."

‘Locked in the Trunk of a Car’

"This is the one song I knew how to treat right away. I really wanted to make it a dark, acoustic, haunting, Hank Williams, Townes Van Zandt thing. Part of it is a minor blues song, the verse, and I remember in my teens watching this interview with Gord and he was really open and he said, 'You know, there was a point in my life where I messed up, I really messed up, and I was living with this guilt.' It’s a song about living with guilt, so as a young aspiring songwriter it really opened this door to me. If you can talk about these human things in this kind of way, this changes everything for me.

"So this song was extremely important in my understanding of how to communicate through poetry and song and lyrics."

‘Courage (for Hugh MacLennan)’

"I tried to sing the chorus on this, and it’s one of those things where I think only Gord can do it. So what you have in the song is just the three verses and Andy Maize of Skydiggers sings the third verse. … Then I realized, why do I need to sing the chorus? Everyone in the country knows it."

‘Long Time Running’

"I’ve always thought it was a great, small-town Kingston ballad. I spent a lot of time around Kingston growing up and you can see Highway 33 and the ferry and the beautiful southeastern pastures. But I’ve always heard this song as a really slow country song, so I took it way down. I really made it about the words and the sparse space of those pastures and rolling landscape. … And what a great story he tells. It’s his early stuff, and a real glimpse into Gord’s matter-of-fact, poetic sensibilities."

‘Put it Off,’ featuring Mary Margaret O’Hara

"It’s one of those dark, broody Hip songs, and just a repetition of three chords. A trance-like tune. But I wanted to amp it up and create this trashy, weird electro song with two drummers and Mary Margaret doing her thing, which is pretty wild. This song, it’s so cinematic. And those opening lines: 'I wrote unfriendly things, truly cruel, on the day that you were born.' It’s like, OK, you trumped me again."

‘Fiddler's Green’ featuring Jenn Grant

"A friend of mine was born on Sept. 17, so we always sing it on his birthday. I understand there is a pretty sad song behind this song, so I really wanted to be delicate and give it as much respect as possible. Which is why I didn’t really want to sing lead vocal. I felt like it required a woman’s touch, so I called Jenn Grant and she was kind and gracious enough to sing lead vocal. I really felt as though it lent to the tenderness of the song. Another case where I relinquished my role as lead singer because you really have to serve these songs."

(This article was originally published in 2014 when Daredevil was released. Purchase the album via Bandcamp.