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Interview: 49 Winchester Frontman Isaac Gibson Talks New Album ‘Fortune Favors the Bold’ & Much More

Frontman Isaac Gibson talks all about 49 Winchester’s new album, ‘Fortune Favors the Bold’ – out today.

49 Winchester
Credit: Joshua Black Wilkins

Formed on Winchester Street in the small mountain town of Castlewood, Virginia (population: 2,045), 49 Winchester started as a group of neighbourhood teenage friends set on a calculated DIY path. In 2014 they independently released their eponymous debut, followed by 2018’s ‘The Wind’ and 2020’s celebrated ‘III’. Now the boys are back with their new album ‘Fortune Favors The Bold’ (Out today – May 13th 2022). Our writer Neil, sat with frontman Isaac Gibson to discuss. 

Hey Isaac, how are you doing?

Great man, thanks! How are you?

I’m good thanks. Happy Birthday for yesterday, did you have a good day?

Thanks, man. Appreciate it. Yeah, I had a bunch of interviews lined up. It was kind of a half birthday, half press day, but it was fun. It’s album release season whether it’s my birthday or not! 

It’s quite a coincidence talking to you as part of the band 49 Winchester. I work in a town in England called Winchester and that’s the name of the street you guys grew up on in Virginia. Potentially a slight difference between the two with mine being full of old cathedrals and relics and yours maybe not so much?

Oddly enough, it may not be as old as the castles and other aspects but I live in the old part of town, which was there before the main highway was built. So it’s got a lot of old relics, a lot of abandoned buildings that aren’t being used anymore. It’s got kind of an ancient feel, feels pretty old school y’know.

I always find it funny when I tell American friends of mine that my hometown has a 13th century Castle in it, and they don’t believe that the 13th century existed because it didn’t exist in America… (laughs).

Right, like history started in 1776 (laughs). That’s kind of what’s drilled into your brain in school throughout most of early childhood in America (laughs). You don’t learn world history until your 11th or 12th grade!

This small town band that is starting to blow up big now. You’ve got some some great stuff coming up as well as all the current bits, ‘Willie Nelson’s Luck Festival’ is going to be a big one. ‘SXSW Festival’ and the ‘Whiskey Myers’ tour. How are you finding 2022 now live music is back; obviously it’s come a long way since the ‘no contact’ concert you guys played in 2020. 

It has. I’m definitely glad to see people standing shoulder to shoulder instead of pod seating and all that jazz that we tried to try to make work during the Covid period. 2022 has been unbelievable so far really. Things have taken this really rapid uptick for us. We’re growing now faster than we ever have probably; ten-fold faster than we ever have. It’s been a great year so far man. The shows have been great. Everything we’ve done as far as singles released from the album and stuff like that has gotten favourable reviews across the board and it’s only going to get better. Busier and better. Bigger shows with the ‘Whiskey Myers’ tour coming up. 2022 is gonna be a big year. I think when we look back at this ten years from now we’ll go ’22 is where it happened’. 

You’ve said that you’re growing exponentially at the moment. What do you think has been the key to that sort of growth as a band?

I think it’s people seeing the fruits of our labor, seeing that we’re rubbing shoulders and getting in with some of these acts that are, you know, national touring acts, people that we’ve kind of looked up to as heroes for the whole ten year period that we’ve been together. I think thats the biggest thing is our touring, our billing on festivals. After this slow climb that we’ve taken, everything’s just sort of spiked. I think it’s largely due to the fact that some other artists that have notoriety and some substance have taken note of us and taken us on tour with them. So that’s a big part of it. Also, signing with a label. When you sign with a Nashville label, you get some eyes on you. So I think it comes down to some good decisions and the culmination of a lot of hard work and a lot of putting in the time over the last eight years.

I find you guys quite refreshing really, as a band, because you never pretend to be anything you’re not. You’ve said before you’re not hotshots out of Nashville and that you’re just hard working musicians. The new album, ’Fortune Favors The Bold’; that’s what it’s all about, right?

Yeah, for sure and that’s how we’ve always operated. We come from a place where if you don’t have that kind of work ethic, you’re not going to succeed. We come from a place that’s pretty poor. Not a lot of people are given a whole lot. Almost everything that anybody has in Appalachia is something that they worked for; if it’s happens to be of any substance. I think that growing up in a culture like that, where you had to have some work ethic, if you wanted to see any, if you want to even sniff success, you know what I mean, you had to work your ass off for it. I think growing up in a place like this really influenced the way that we operate as a band, which is hard hats on go to work kind of stuff. So it’s a very blue collar approach. But that’s what’s benefited us. I think that’s a big part of why we are who we are.

49 Winchester Album Cover
Credit: Kelly Wills

Throughout the album, you’ve got that story sprinkled throughout. ‘All I Need’ tells the story of being packed in a van playing live music. 

Yeah, that’s a good feeling. That was something that seemed like a pretty far off dream when we first started this eight years ago, as a bunch of high school kids that had never been in a band and didn’t know what they were doing. Had absolutely no knowledge of the music business or anything regarding that. So everything good that happens for ’49 Winchester’  just feels like icing on the cake. We never expected to take it this far and we certainly never expected to take it as far as it’s gonna go… But at the same time, I think we did y’know. That dream was always alive. It seemed like the odds might have been stacked against us. But I think in our hearts, we always knew that if we just stuck at it, kept it up, kept grinding, kept working hard, we could see some some real benefit and do this for a living. That’s what we’re doing. And that’s all I ever wanted out of life. 

I suppose it’s quite an organic process with you guys being high school friends. You played music because there wasn’t really too much else to do apart from getting in trouble with the law when you were growing up. How did you find growing up and evolving into the music scene from a small town? That must have a lot of challenges on its own, rather than doing it from a big city?

Certainly, yeah. It definitely does. Being so far out and even with us being so far away from anywhere that even has a tiny music scene is tough. We cut our teeth in our local scene in the trie-cities area; Bristol, Virginia, Johnson City. But that’s an hour away from home even. So we’re so far out in the sticks that we had, you know, to first take root in this really small trie-cities music scene and we milked it for all it’s worth man (laughs). We still love playing at home. That’s where we learned how to perform; in front of our hometown crowd and I think a lot of times your hometown crowd is harder to please than anybody else. So I think it’s made us better performers, I think it’s allowed us to to keep pushing the envelope. It definitely has its disadvantages, and its challenges, but I wouldn’t, I don’t think I would change it for anything else. It’s it’s been pretty influential on who we are as people and who we are as a band.

Would you ever consider a move to a bigger city or did you guys consider a move previously?

No and I still don’t. We’re really fortunate. I’ve talked about this a lot lately but we’re really fortunate to be in a time when you don’t have to live in Nashville, LA, Austin or wherever else to have a successful music career. The internet changed all that pretty much overnight, you know what I mean? It’s cool to be able to be a professional musician that still lives here in central Appalachia, in the middle of nowhere. That keeps us authentic I think. This being where we come back to, to experience the same places and the same faces that we have our whole lives, I think it keeps you grounded and it keeps you honest as a musician. I think it benefits me as a songwriter, too. The reason I write songs, the way I do is, is because of the place I’m from and the people that are here. And being here when we’re not on the road is very important to me. I was born and raised here. I’ll live and die here as long as I can. Being here has been a big part of keeping ’49 Winchester, 49 Winchester’.

Let’s talk about the new album. You’ve had a relatively short break from the previous album ‘III’ which you released back in 2020. Was there much of a difference in the writing and recording of these two? If it ain’t broke, don’t fix it ideology.

I think so. This was our first time doing anything besides a very independent approach. So this was something we did with a record label and a co-producer. The process itself was a little different. But I think the thing that really changed the most between ‘III’ and ‘Fortune Favors The Bold’ is just us, I think we’re just better. We’re older, we’re more seasoned. We’ve been on the road for the last two years since that record came out. I think we’ve just evolved a lot musically. I think I’ve matured a lot as a songwriter in the last couple of years and the record reflects that. I love the album ‘III’, I love every song on it but this record is a different beast. I’m already looking forward to getting in the studio again. I’ve got maybe almost a whole albums worth of material again!

An album a year hey?

Yeah. That’s the grind. That’s part of it. If it’s possible, I’m not one to push my writing, I don’t sit down for an hour every day trying to write a song or anything like that. When they come to me, they come to me but I’ve had a recent wave of creativity come over me. I guess it’s about time to get back in and start working on another album. I love the lineup we’re playing with right now. Our touring band, which is not the same lineup that’s on the record, is getting bigger, better and badder. I’m super looking forward to getting this record out. We’re looking forward to get getting back in the studio and doing more of it. I think that’s a key to staying relevant. I think that’s a part of why Charley Crockett has enjoyed such great success recently. It’s because he never stopped putting out music, there’s always something to latch on to, something that comes up in the news feed, something that gets your eyes and attention on Charley. I think releasing music often is part of that trick. Even though it’s been two years between every album so far, we’re gonna shoot for one year on this.

I understand the challenge though. I was chatting to a musician recently who hadn’t released anything new in five years. Although it is a longer period of time, he just had a family and had some big life events happening. Everyone was getting onto him about it.

It’s hard to find time to live a normal life, to have a family and do things like that. It always has been. It’s been a tough thing to try to balance the home act and the road act, you know what I mean.

Your production team on this record; you’ve obviously worked with Kenny Miles and Stewart Myers before, what is it that you think works so well when you guys get together?

Man, I think that with our sound being something that’s kind of unique, it’s not easy to put a finger on. I think it’s important to have the right guys in place. Since we met Kenny and Stew, they seem like the right guys, they knew they had this understanding for who we are musically, you know what I mean? I think that really allows them to use their talents on our records better than I think anybody else could have. They’re great at what they do. Stew was such a help with all of his input on the really subtle nuances and things that make a good record a great record, you know what I mean? Kenny was the same way in the post production sense. I’ve always loved Wayne Graham albums. The records are always so huge in scale. They’re deep, and they have this dynamic and depth about them that I’ve always loved. A lot of that is because of Kenny’s talents in the mixing booth. So I don’t think you could have picked a better couple of dudes to do it. I think it’s just because they get it man, they just understand who we are what we’re about, and that we’re kind of a no compromise gonna make our kind of music kind of band, and they roll with it.

You’ve dropped a few singles from the new album but is it still a bit of a mystery to people otherwise or have you played it live yet?

Just recently, maybe in the last month or so we’ve played quite a bit of it live. But 99% of ’49 Winchester’ fans haven’t been to a show in the last month. You can only play to so many people at any given gig and when your audience is growing the way that ours has, there’s always, you know, tons and tons of people who haven’t heard a molecule of new music. So getting that out is gonna be really exciting. I’m looking forward to it. I’m glad we got to release the three singles that we have so far. I think those are the right ones to do. Gotta give kind of a feel for what the album is all about. New singles coming out really soon, too. So keep your eyes peeled for that.

I’d like to delve into a couple of tracks on it on it. ‘Annabel’ was the first single to be released. Can you tell us a little bit about how that one came about to begin with?

Yeah, that was actually a really old ’49 Winchester’ song that we played when we were totally different instrumentally. It had a banjo in it and all kinds of stuff that was not what it is now. When we got into the studio for ‘Fortune Favors The Bold’ we had time together. For the first time, we weren’t paying for a studio out of pocket, scraping together a few hundred bucks here and there and sticking it in a savings account for studio time. You know, we really had time, ‘New West’ provided us with a platform to just hunker down, really stretch our legs on everything we wanted to and flesh things out fully to get things the way we wanted them. We didn’t know how ‘Annabel’ was gonna turn out musically when we started recording it but we decided to cut it in whatever way it happened. It turned into a totally different animal with that big baritone guitar line, all that reverb and the vocal harmonies. It was interesting how it just changed and morphed, the more layers we put into it, the more it kind of just created itself, you know what I mean? We just sort of let let the song benefit the song. I think it wound up being one of the best songs on the record.

If I was to sum you guys up in one word it would be organic because everything you do seems to just fall naturally.

I’m a big believer in things happening for a reason. I think that there’s been a lot of ’49′ things that feel that way. They just come about just the way they should you know what I mean, things just kind of fall fall into place for us a lot of times, whether it’s a musical idea, or an opportunity of some sort. It just seems like there’s a lot of a lot of wind in our sails right now and it feels really good.

You said earlier about not sitting down to write for an hour a day but do you guys have a schedule for when you meet to write new material and the like?

No, we spend so much time together that usually I’ll bring the guys a new song via cell phone recording, it’s not even at a rehearsal or anything. Just a way to get the progression and the movements within the song done and they can then work in their own parts. I think that’s why ’49’ has been able to maintain a lot of that integrity as far as our sound being different and unique is because I’ve always done that. I’ll write the song progression, lyrics, you know, and give the song to the guys and let them flesh their parts out. Then we just start it out live. We’ll throw it in the setlist. If it kills it kills, if it bombs, it bombs. 

I think our bombing days are about done though (laughs). We’re not the younger musicians that drank a lot more beer than the musicians we are today. A few run throughs live and stuff gets really tight with this group that we’ve got. That’s kind of how songs usually come about, they sort of work their way in one by one as often as I write them. So it’s always been that way as far as my writing process. It’s just kind of take it as it comes.

‘Russell County Line’ seems like a pretty personal song to you guys?

Yeah, for sure. I mean, that’s the home anthem, you know what I mean? That was both a nod to the woman that I love and the place that I love. Russell County and the surface level of it but also to my girlfriend Olivia, it’s a love song to both so that song means a lot to me for sure. I’m glad people are enjoying it.

In the video, you’re back in your old stomping grounds. Are the places that you’re sitting in the video, the places you would sit back in the day?

Oh sure. Yeah, that is the stomping grounds. That’s Winchester Street in Castlewood. That’s all within a quarter mile of where me and Chase, the bass player, grew up so that’s the home place. 

It does give listeners an authentic look then! ‘Damn Darling’ is a little snippet into Nashville. Can you tell me a little about the thought process behind this one?

I think that song mostly started with me trying to push myself a little bit as a writer. I’d gotten to where I felt like too many of my songs were from a first person, introspective point of view. I wanted to write in more of a storytelling way. It was me trying to step out of my comfort zone and think outside the box a little bit. So there was this this idea that I had in mind which is; heartbreak is universal, across space and time, you know what I mean? There’s always some poor sad sack crying in his beer in a honky tonk, that’s a tale as old as time. So I think it was me telling it from a different perspective. The first line of the song ‘was the night before Christmas, 1995’, I was a year old in 99’ (laughs). Coincidentally, I was listening to a lot of 90’s country at the time and I think that’s what put the setting in my mind. The song was just a story wrapped loosely around that. So I think that song came about as an exercise to write outside of the box a little bit and come from a different perspective. 

But also, I think with your writing, it’s got a simplicity and elegance to it, you don’t overcomplicate things. 

That’s a trademark of a lot of great country songs that I love. The writers and bands that I look up to and how they write the songs that I love are often the ones that are delivered that way. There’s not too much emphasis on putting the flair and the spin on s**t. It’s just really telling it how it is. You know, so cliche to say it, but three chords and the truth, you know what I mean? That’s what really makes a lot of great country music, it’s just somebody willing to put their heart on their sleeve and write something with some sort of truth in it. I think people latch on to that. And that’s why people love country music. That’s what makes it great.

I’ve figured out my next big country song that I’m gonna write after this is going to be about the fact that you’re three years younger than me and you can grow a much better beard than I can!

Well (laughs), it looks better on camera a lot of times. A lot more often, it’ll look like this (mimics a lions mane and laughs).

The song ‘Neon’ has got some beautiful keys and organ on it. Is the band going with a full lineup including keys on tour?

Yeah, we are now. Don Eanes is the one that played keys on that record. He toured with us for a little while too but he’s not touring with us anymore. Don has been all over the planet. He’s played with some global, contemporary Christian acts. He’s the coolest musician I’ve ever met in my life. The stuff he does with keys is unbelievable. But the guy we’ve got playing keys in the band called Tim Hall, he’s a hometown guy from right up the road. He’s about 40 minutes up the interstate from Castlewood. He’s 22 years old and he’s an absolute beast. So super, super glad to have Tim in the touring band but it was really special to have Don in the studio. The best moment in the studio was when Don was recording and doing tracking stuff on ‘Last Call’. When he does that solo, the piano solo on that; the whole time, it sounds like it’s gonna fall off the rails. We’re sitting there on the edge of our seats listening to him the whole time, we’re like ‘oh, oh, he’s gonna drop it. Oh, he’s gonna oh’, and he comes back around and slams down on the one with that big slide. Yeah, man, it was fun to have done in studio for sure.

You guys have got a record label now but the fact you were independent and you grew independently for a long time is something in itself. Do you have any advice for musicians and bands that are starting as independent at the moment or have been working through it for a couple of years?

Yeah, you should be independent because you want to be independent; and not because you think that a label is something to avoid or something that you’re above. If you’re going to be an independent band, it’s important to know when to let go of some of that and take on the pieces and the parts that are going to help you grow. But it’s important to find the right pieces and parts because an independent spirit is always about the right pieces. It’s about keeping the circle small. It’s about keeping the integrity of things the way that it was when it started, you know what I mean? A lot of times, that’s why guys want to stay an indie band. They don’t want to waver or concede any creativity or anything like that. So that was why it was such a great experience for us with ‘New West’ being is the artists label. I mean, it’s the ultimate artists friendly label, total creative freedom over everything. Yeah, an upcoming indie band, stay independent. It’s cool. But when the time comes, the right people come along and the fit is there, take that fit because it’s it’s it helps a lot in the long run, man having those other people on your team…

Have you guys got any plans to venture over to the UK soon?

Yeah, yeah, nothing officially scheduled or anything but it’s looking like probably a summer or fall 2023 Europe tour. That’s what we’re hoping for. I would love to go overseas. It would be cool to come over as a support act for one of our label mates or whoever makes sense. But if it’s a headline tour, we’ll be super stoked about that, too. Hopefully next year, we’ll be crossing the pond for the first time.

Yeah, definitely. That’d be a pleasure to see. Well Isaac, thanks for taking the time out today. Appreciate it. 

Thanks man, great meeting you. Have a great day!

49 Winchester’s album ‘Fortune Favors the Bold’ is available now.

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