When it comes to record companies that changed the face of modern music, few are more legendary than Chicago’s Chess Records. Founded in 1950, the label specialised in rhythm and blues before expanding to jazz, gospel, soul, and early rock & roll. It was where late rock & roll icon, Chuck Berry, released his recordings, together with the likes of Muddy Waters, Etta James, and Bo Didley, to name a mere few.

Being sold in the late 1960’s, the record label's vaults remain a historical treasure trove and now a talented singer from Canada, Elise LeGrow is bringing a selection of the Chess Records classics to life again on her sophomore album, Playing Chess. Working with The Root’s QuestLove and S-Curve Records founder, Steve Greenberg and R&B legend, Betty Wright, LeGrow’s soulful re-workings of the Chess back-catalogue bring some of the most iconic songs from music’s history to a new generation.

Speaking to LeGrow ahead of the album’s release in October, she talks about the joy of unearthing records from the catalogue, the complexity involved in reworking the records and in bringing the records to live audiences.

DiS: How did the idea for the album come about?

Elise LeGrow: I flew down to New York in February 2016 with a guitar player and we did a little showcase at S-Curve. It went really well. After that, we started figuring out what we were going to do together. Steve had this wonderful idea to do an album of songs from the Chess catalogue – this is Steve Greenberg I'm referring to – and S-Curve is his baby, and so too really is this project to a certain extent. It was his idea. We poured over the material for months, sort of comparing notes and digging because some of the songs actually required a certain level of excavation just to find them.

What the process behind finding and excavating those songs from the Chess catalogue? Was it a difficult process?

It was challenging because there was so much music in the Chess catalogue. Just actually going through it all and listening to all of the music [was challenging] as we wanted to do for a thorough job. We knew that there was some really great stuff that may not be in all the anthologies but a lot of my research was on Spotify, Google Play and Apple Music, because I wondered whether there might be songs that appeared on one of the music services that wasn't in the catalogue. We were scavenging and scouring through Wikipedia pages and things like that, looking for clues to where all the recordings were.

It was a bit of a scavenger hunt. The artist Sugar Pie DeSanto, who I had never heard of before, well I discovered her in this process of searching through Chess. We do a song that she recorded called ‘Going Back To Where I Belong’. It was really a matter of following several rabbit holes to the end and then finding this gold at the end. It was exciting.

It all culminated in about a seven-hour meeting [laughs] at Steve Greenberg's office where the three of us sort of sat down together and compared the notes that we had arrived at, and shared songs with each other. We played lots of songs in that room and in the moment, gave our immediate responses and our feelings about them. It was really important to me that the songs that we chose were things that were in some way relatable to me – a story that I felt I could honestly tell.

Was it hard narrowing the songs down for inclusion on the album?

It was, it really was. Even after all of those months of our own individual research, coming together, we still ended up with, you know, even at the end of that seven-hour meeting we still ended up with a list that was [laughs] far, far beyond an album's length.

It was really challenging because there's just so much beautiful music. There were a few songs that I intentionally steered away from because I didn't feel like I could sing those words believably like the song ‘I'd Rather Go Blind’. It’s a gorgeous song and it's like a sacred recording - but I couldn't do it believably. At one point, we were considering doing that song, and as I was sort of singing these songs in my head or at home or wherever, but I just couldn't sing those words. So yes, challenging to choose but it was also a delightful process.

What was the process of recording the album like once you'd chosen the songs?

We recorded a significant portion of the album in New York City, and then another portion in Toronto, over several months. We started in the fall of 2016, around the end of October – I remember I was in New York on Halloween, I don't remember the exact dates – it was right at the end of October that I flew in. Then we had several days at Mission Sound in Brooklyn and then at Bunker Studios, also in Brooklyn.

It was an awesome process. I'm not a producer, I was looking for direction from Steve and Mike but what was smart about the process was that I hadn't made a record like this before. I think they made a wise choice letting myself and the band figure shit out rather than [telling us what to do]. For sure there were concepts, we had rough ideas of how something might go, we certainly wanted to make the very well-known songs radically different than the original recordings, you know?

There was a sort of general roadmap, but other than that we had a lot of freedom, we had time and freedom to try things out. I think that's why some of my favourite moments on the album were the result of that – of just myself and the guys just going at it until something cool happened [laughs].

It was a really great process. It was certainly a thrill to have members of the Dap-Kings, Captain Kirk Douglas, Questlove came in and played drums on a track written by his father all those years ago. It was kind of a surreal experience. I don't know, I had never known Questlove personally prior to this, but he's on television every night. Obviously, I'm aware of his other successes, but primarily that was as far as I knew of Questlove personally.

It was really a surprise and a thrill for Steve to say, 'Oh yeah, I called up Questlove's manager and he's going to come in and play drums on the track. It was really awesome being a relatively unknown artist from Canada. Anyway, yes, recording was great. Honestly, I live for the live game, but this process, this recording process, was really a lot of fun.

It sounds like it was an incredible experience.

It really was. And I had Betty Wright – an American soul legend – she was also there every step of the way, infusing her own magic into everything. That was really great too. Having that support of somebody who's [so experienced]. She's a singer, a writer and a producer. She has a career that I dream of having – spanning several decades and genres, and she's done so much interesting work. She's really somebody. Having her fingerprints on this really meant a lot to me.

What was the biggest lesson you learned from this experience?

The greatest lesson during the recording I would say is simply let the music happen. I had a lot of anxiety, frankly, going into it because this was a really big deal to me. I remember having nightmares about waking up with laryngitis [laughs]. I don't know, sleeping in through a session or something – the kinds of dreams you have before your wedding day or your first day at your big job or something [laughs], a day that really matters to you. This really was a huge deal to me; I had a lot of anxiety going into it.

The first day I was going in to work with Betty Wright especially, I really wanted to impress her: I wanted to do a great job. I would say to my future self: "Just relax - let the music happen – what you do, just do it!" [laughs]

What's been your experience of touring so far and what are the tour plans once the album is released?

I've already done a few shows in the States with a fantastic band some of whom actually played on the album. That was a real treat, you know, getting back with those guys. I've done quite a bit of touring – we've now done a few dates in the US, and we're going to be touring quite a bit more there. And also in Europe starting in the fall. The live show is very much a reflection of the album. Of course, there are nuances here and there, but for the most part what you hear is what you get. We're kind of just laying the groundwork for all that now, but really that's the thing I'm most excited about – getting out there and playing these songs live.

Did you have the live band in mind when you were planning the tour or did that emerge organically?

First of all, I should say there's a band in Canada that I've been working with for a few years and a lot of these guys will be joining me on the road for the next haul. But the shows that we've played so far, a lot of those guys were based in New York – I actually didn't know a lot of guys in New York, but the label's based there. A lot of those artists, a lot of those players, rather, are also in the band of another artist on the label called Michael Bloom who is really great artist. I basically borrowed his band for a while [laughs].

Some of these guys for sure will be appearing in future shows, and they were great to work with, but Michael's going to need them on his tours coming up. So that'll be the time when the band from Toronto I've been working with for years will have an opportunity to step up and come out with me. Prior to that, just logistically, it was easier for the label to sort of work with people they were familiar with. And the touring we've done so far was exclusively in the States and they're American, so it was just kind of easier. Going forward, as we're venturing to other countries it won't matter as much where the guys are from – Canada or US – so my regular band out of Toronto will be doing a lot of the touring with me going forward.

The guys in Toronto I've been working with for a few years, so there's certainly a level of comfort and the cohesion that sort of happens naturally when you've been working together with people that long. These guys are like brothers to me so it'll be great to get out with them.

What music were you into growing up and when did you start to make and record music?

It's kind of funny because I actually don't recall when it happened. But my mother tells me that when I was like four, I declared that I was going to be a famous singer and that was what I was going to do. She was always very supportive of me. Neither of my parents were in the business or knew anything about the business [laughs] or anything like that, so I was sort of left to my own devices in many ways. They always encouraged me to sing for sure. I would sing at family gatherings, and school talent shows and stuff like that growing up.

But by no means did I have stage parents or anything like that. I was sort of left on my own to a certain extent, which I think was great because I learned to love music on my own. And I think that's kind of why my music tastes are so eclectic. It was nice to have that independence. I think a lot of kids have a lot of structure in their music learning, and it can be really beneficial but it can also put you in a bit of a box – it was nice to have all that freedom. My uncle's a musician, my grandfather was a musician, and so there's definitely music in my blood.

Were there any particular artists who you kept returning to influence-wise?

It kind of changed over the years. Admittedly, when I was really, really young, you know, school talent show-aged young, I was singing Disney movie songs [laughs]. Obviously, I've come a long way since then! [Laughs]. But in between there and where I'm at was The American Songbook, I was singing jazz and classic jazz for several years in my teens. Then I kind of made my way forward to soul music, R&B, blues and soul, and then I landed there. It felt really good to me.

Some of the songs on the record are not R&B songs, but I think there are always—generally there are soulful elements. Even ‘You Never Can Tell’, which is not on its surface an R&B song, has got those beautiful soulful backgrounds which kind of give it that colour.

Did that feel more poignant in light of Chuck Berry's passing?

This is what's so eerie about the whole thing; Chuck Berry passed away in between the finishing of our recordings. When we were recording, myself and Steve and other people in the room, we were imagining a scenario where Chuck Berry would actually hear our renditions of these songs. That would’ve been really great. That would’ve been really cool. Obviously, it was devastating to have heard that he passed away in between the recording and the release of the album. It was very sad news.

He was just a giant, of music

Absolutely. I mean, they sent him to space, jeez, I remember hearing that story about the—not the time capsule, but…I can’t remember what they called it – space capsule or something? [Laughs] like Beethoven and Chuck Berry. And there’s that great SNL skit [laughs] where the aliens write back, "Send more Chuck" [laughs].

Has covering the artists you have made you a more confident composer in your own right?

Absolutely. I think interpretation is crucial in development. I think the study of any craft generally involves years of research and interpretation of art that’s come before. I didn’t have a lot of sort of formal school music training, but certainly, music listening and interpretation has been something that I have actively engaged in since I was a small child. This is one step in that journey.

And these songs are beautiful – they’re the underpinning of a lot of rock and blues and R&B that I grew to love that was made years later, but, you know, was founded in a lot of this music. Like you said, Chuck Berry is heard in all of the great rock n’ roll going forward. I'm a huge Beatles fan, a huge Stones fan, and you hear him all over that stuff. I feel like it was a gift to be able to make this record.

What was the most challenging and enjoyable thing during the process?

That’s a hard one [laughs]. Okay, what’s challenging? I would say one of the most challenging things was interpreting ‘You Never Can Tell’. There’s a melody that you hear in our recordings which was written by Steve Greenberg in the ‘70s before he had ever heard Chuck Berry’s recording. He had this book – this is a really interesting story, actually – he had this book of rock n’ roll legends, you know, chronicling the life and times and work of rock n’ roll legends. And an entire page of that book was dedicated to the lyric of ‘You Never Can Tell’. And while he had never heard the original recording, he came to know this lyric and he wrote his own melody to go along with it.

It was years later that he actually heard the Chuck Berry recording, so in his mind, that was how the song went [laughs]. When we went into this I had only ever heard the Chuck Berry recording, and so in my mind that was the song. It was definitely a challenge for me, you know, finding my own voice in this new melody. Steve made no presumption that we would necessarily do his rendition of it, but he pitched the idea. He sat down and he played it on his acoustic guitar, and he sang it in his Steve voice [laughs]. It was great.

I fell in love with the melody that day. But for years prior to that I'd been singing this song in my own way based on the Chuck Berry recording, and so it took some time to find my own voice in this new melody. That was definitely a challenge. But it turned out great. I think Steve just had a dream of recording this song this way for decades. It was kind of a cool and surreal experience for both of us – me having never heard his rendition, and for him having had this melody in his head for, you know, 30 years prior [laughs] and finally having it manifest on this recording. It was a challenge finding my voice in that melody.

And what about the most enjoyable moment of the process?

Okay, well, one of the most enjoyable moments actually happened really early in the process. It was the very first song that we recorded together – myself and the band all in the room together – that was when we were recording ‘Who Do You Love?’ That was the very first song we attempted to do together.

We were just working stuff out at this point. We had a sense of what we wanted to do but we were really working things out. And just in one of these little jams that we were doing together, I arrived at the melody that you now hear in the chorus and that just kind of came out spontaneously – so that was cool because it just happened and it kind of feels like a magical moment when you didn’t have a melody and now you have one [laughs]. So that was really fun, just that.

But then also, later, moments later, in the same take I believe, as a group we all kind of arrived at the breakdown that happens in the song – around, I don't know, a couple of minutes in – there’s a breakdown where the music almost completely cuts out, I start singing this repetitive line: ‘Tombstone hand/Graveyard mind’ and that all happened kind of spontaneously as well. That’s one of my favourite records on the entire album – that breakdown and the swell that happens leading into that final chorus.

So that was really cool. Coming from a jazz background especially, with the energy of the live show - it kind of felt like that. It kind of felt like because we arrived at it together and it was unplanned: it felt like a true jazz moment, sort of improvising and somehow just working. That was really cool and one of my favourite moments.

That’s why I love the live shows – it’s when those things happen. Or at least if you’re given the freedom to do that. I think some people approach the live shows differently. Certainly, we’ve worked out some kinks and things by this point. And now there is a joy in recreating those moments together. We’re not improvising on stage certainly as much as we were when we were working out the arrangements, but having the ability to sort of relive - I do feel a little bit like I'm reliving the moments of creation when I'm on stage with these guys.

Playing Chess is out via S-Curve / BMG Records on 6 October. You can find Elise LeGrow on Facebook and Twitter.