An interview with local band Winston Ramble: new releases + special Nov. 27 show

Catching up with Justin Oliver and Drew “Ben” Benefield, two of the founding members of Winston Ramble, about their annual Thanksgiving Eve show at Saturn and their new release of Heaters Volume III.

Lemme set the scene: It’s a dreary Saturday afternoon – Ben drives up from Hayden and Justin comes from Southside to my home. I’ve known of Winston Ramble for years, and since 2019, I’ve been lucky to be pals with these fellas (and even bandmates with some of ’em!). So this is not the first time we’re meeting, but it is the first time Justin, Ben and I have done a deep dive — just the three of us. Here’s what I learned:

I know y’all grew up together, but what was the spark that brought the band together?

Ben: Justin and I were high school buddies, and we wanted to get together and play music with our friends, so Justin, Judd, Max, Martha and I did just that. 

Can you tell me a little bit about the origin of your band name? Is there a meaning behind Winston Ramble? 

Justin: We’re from Haleyville, AL out in Winston County, so we wanted to connect with that.

Ben: And a “ramble” is a jam session, a musical throw down or a hootenanny. That’s what we wanted to do. We wanted to play music with our friends. Levon Helms from The Band used to have midnight rambles where folks would come to play music all night.

How long has Winston Ramble been performing together? 

Justin: Marty’s was our first show ever on September 20, 2012.

Ben: At that time, Marty’s was like our version of Litty’s [also known as Little Italy’s – the beloved Five Points hub of Birmingham’s singer songwriter scene. It closed in April 2022 with plans of relocating]. I auditioned to play there in front of Marty himself, and I got the gig!

What genre does Winston Ramble fall into?

Ben: When we first started playing together as a duo and then as a band, we used to call ourselves folk n roll. But now, we rock and roll and adapt to who we’re playing with and how new players or new band members interpret our songs. It’s changed a lot with the three new guys (Taylor, AJ and Ryan), but we didn’t do anything on those first recordings that these players can’t do. 

How has Birmingham and Alabama shaped your sound, your vision and y’all as band?

Justin: I think whether we try to or not that we have a distinctly Southern sound, a Southern voice. Birmingham was the best place for us to grow and find our sound as a band. Both in terms of finding how we wanted to sound and the people we play with now. We wouldn’t be playing Saturn now if it weren’t for our friends and supporters in our early days.

Ben: Growing up in northwest Alabama at that time was everything. It shaped what we were listening to, how we were playing and who we wanted to be. And then coming to Birmingham, where it was such an open music scene, we could grow however we wanted to grow. Birmingham had (and still has) so many different spaces for so many different genres.

Who makes up the current Winston Ramble line-up?

Ben – lead vocals and guitar

Justin – vocals, mandolin and harmonica

Taylor Goodwin – lead guitar – joined in 2019

AJ Covey – drums/percussion – joined in 2021

Ryan Brown – bass – joined in 2022

And for hometown shows, Daniel Raine of Little Raine Band chimes in on keys.

Ben: What we do is not a set thing —like the Grateful Dead— we could have different people sit in or we could all be up there playing maracas and cowbells. You never know what you’re going to get, but we can promise it’ll be a good time.  

What is the creative process for the band? How do you guys create/build songs? 

Justin: Everybody puts their stamp or their spin on it, but usually, Ben or I will have an idea, and if it feels right, we offer it up to the band. With “A Whole New Way,” I had the musical part and some lyrics, so I brought it to the guys to play around with. As they interpreted the song, I listened, grabbed a piece of paper, and the rest of the words fell out of me.

Ben: I try to give Justin space if he’s cooking.

Can you tell me the significance of the 4th Annual Thanksgiving eve show? Is there anything special in store for the night?

Justin: It’s our first official Winston Ramble show in Birmingham this year – that alone makes it special. It’s turned into the show that all of our people come out to and the one we most look forward to. It gives us the opportunity to plan more of a show every year. To make it stand out from the last one, so it’s artistically significant in that sense. You have to come to Saturn to find out who’s playing 🙂

Ben: It’s like our own personal Friendsgiving, but instead of the food, we’re serving up rock n roll and jams but no turkey. 

How does Winston Ramble measure success?

Justin: For me, I’d say success is how it feels when we play together. And the energy that we have toward each other. That connection means more than if we sell out a show – the crowd is a huge part of the experience – but I measure success by “did we capture the moment we were in while we were in it?”

Ben: The live setting. The fact that we’re having a show at Saturn on 11/27 – the fact we’ve been able to play together for this long and that people continue to show up for us – that’s success. 

In over 10 years, what would you say your most transformative performance was?

Justin: All those moments along the way have been significant – that first show back in 2012 was a huge moment for us. And then moving to different venues — playing actual music venues instead of bars— was a big step too. Having our first proper tour back in 2017, where we spent two weeks in a van playing 11 shows. After we ended that run with the last show in Birmingham, that was the first time when we were like “OH SH*T people came to hear us play.” 

Ben: We’re all on the same page at the same time – we’re all in the moment, in the groove. We bring the feeling or vibe of a new idea Taylor, AJ and Ryan bring the “know how.” They get us there – they help us execute our attitude. They’re the perfect guys to bounce our sounds off of and they understand what we mean. We’re listening and responding to each other better than we ever have. 

Justin: The more meaningful moments are when we’re playing live, and we don’t know where we’re going until we look across the stage and we recognize that this is Winston Ramble – this is what we do. 

How do you continue to grow, learn and collaborate with each other as bandmates change and life priorities shift?

Ben: We really are like a family or a gang. The original players (Judd, Martha and Max) are brothers, and when they left, Justin and I felt like it was important to develop similar, deep bonds with new players like we had with the friends we had known for all our lives. All of these guys are our brothers. 

What do you want your audiences to takeaway from your live shows/performances?

Justin: Hmm, that’s a thinker. I want people to have fun and to be entertained. And I hope the music elicits some type of emotion – whether it’s sadness, anger, happiness, anything. It could be one lyric or one guitar solo – it would mean the world to me if someone could Feel It.

Ben: I want people to forget the world as they know it. We’re all in the same room, and we’re experiencing different things. I want people to be sucked into the environment, the music, the whole experience and say “Man I completely forgot about work today.” Or maybe you shed whatever you’re carrying. I want each person to feel like they got to let go for 90 minutes, 2 hours or however long we were playing. 

What do you believe keeps people coming to Ramble shows and/or streaming your music?

Ben: I’d like to believe there’s a feel good factor — a period of time to let loose or a means to build a community. I think the community sort of feeling makes people wanna come back to a show. 

Is there any big news to share with your fans? Any upcoming releases?

Justin: We’ve got Heaters Volume III releasing on November 22nd. Working with Brad [Brad Lyons of Boutwell Studios] has been awesome. It’s been fun to record and release some covers we’ve been playing for a long time and reinventing some older Winston Ramble tunes. 

Ben: And we’re planning shows for 2025. We’re so ready to play. 

Do you have any current Birmingham artists you’ve been listening to recently? 

Justin: Mountain Grass Unit – they’re my number one of all music right now.

Ben: It’s so cool to see Mountain Grass Unit on Billy Strings’ page. Lemme add Little Raine Band – we’re so close to those guys, and it’s cool to see them changing and growing just like how we are. And everybody at my house loves the Stepdads.  

Justin: There is a ton of talent in and around Birmingham – it would be an injustice to not list everyone we know playing in this town.  

Do you have any words you’d like to leave BhamNow readers with? 

Justin: We have a good show planned for the 27th, and we’d appreciate it if you feel like joining us for it. We hope to see you there!

Ben: I just wanna say one last thing, and that’s rock n roll.

It’s a different experience to hear their music live than it is to sit in my safe space and talk with Justin and Ben about what it means to embody Winston Ramble — to capture a moment, to connect, build and grow and to be a brother. 

You’d be doing yourself a disservice if you weren’t at Saturn on 11/27. I’ll be there, and I’ll be looking for you in the crowd.  

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If you dig stories like this, please let us know @bhamnow or leave us a comment. If you’re not able to attend Ramble’s November 27th show and you’d like to know about future Winston Ramble shows and upcoming releases, give @winstonramble a follow on your preferred social media platform.