It’s about 6:45 on a warm, breezy Saturday evening on a rooftop overlooking Brookline Ave. at Fenway Park when Will Dailey makes a pronouncement about his career and immediately rescinds it. “I’m just going to play places you can bring kids to from now on,” he says while musing about the vibe of this Fenway Rooftop Session and announcing his next gig at the Festival at the Farm. A second later, after a chuckle, he adds, “I just said that, and it’s maybe something I don’t want to commit to.” I think we all knew he was kidding, but he felt the need to clarify because of something fundamental about Dailey. He’s thinking about each person in his audience, and he’s thinking about the connection he has with them.

“[It] also goes back to working every record until I know somebody who thinks a particular song—and each song on the record is covered—was made for them," Dailey said last month when we talked about Golden Walker, his latest release that dropped earlier this summer. "It could be a stranger, you know. It could be my best friend. But that’s the intention. Not an audience or a broad audience or a genre. It’s engaging the person—even if I don't know them—who needs this right now. And I’ll feel better knowing that we're connected through this piece of music.”

Dailey’s heterogenous approach to songwriting—what he describes as a musical pluralism—results in a style that’s difficult to pin down. Early critical notices lumped him with a mid-00s burgeoning Americana/roots boom, which is understandable given the acoustic orientation of 2004’s Goodbye Red Bullet, and 2006’s Back Flipping Forward. But digging into the deeper cuts on those records hinted at an artist pushing toward a broader sensibility. This mainly succeeded in casting Dailey into the “Indie” waters of musical miscellany, as it became more difficult to spot his style, and was fully realized on 2014’s National Throat, which has been Dailey’s most lauded record to date. Despite any worries that the vagaries of genre identification might put him at a disadvantage in a rapidly shifting industry, Dailey points out that his inclusive approach to music-making extends from a broader sense of how he approaches his life and art.

“I don't want to go through life being one thing. Certainly, artistically," Dailey said during our interview."I like going through life being attached to one person that I love and dedicating myself to people I love. But with art, I want to be able to try everything.” And that disadvantage is precisely what he means to challenge with Golden Walker.

“If I made everything exactly like ‘Bad Behavior’ or everything sound like ‘The Submariner,’ then the algorithm picks up a lot more for me because the algorithm then feeds you to the people who like that beat-per-minute, who like that key, who like that tonality and voice, and whatever it is,” Dailey said. “So the more you make the music a little more homogenous the more you benefit from things like playlist placement. I wanted [Golden Walker] to be the thing where you maybe discover ‘Bad Behavior,’ but then you put it on in the context of the album and you’re kind of like, ‘What the hell is going on here?’ You have to stop and think about it and engage with it personally."

“So I feel like I'm making this record almost as a response to the algorithm taking over too much, trying to fight the atrophy that can happen when we don't stop and listen to things,” Dailey continued. “I think the album is only one part of making music. It’s an art form. So when you're doing it, it should have a whole vision, a whole reason for existing.”

The album—as an artwork—has become so conventional, that it can escape our attention that making one can still be a statement. And in a mediascape increasingly dominated by playlists, insisting on a vision for an album becomes an audacious act. Will Dailey is well aware of that. At one point in our interview, Dailey said he can see himself making one more full-length album, and following it up by “exploring all corners, and taking advantage of digital music,” recognizing the shifts in distribution that now define the music industry. Making an album encourages audiences to listen in a particular way, and while some of those listeners are dedicated to tried formats—National Throat was issued exclusively on vinyl for a period, after all—new encounters with music have taken on varied dimensions, and artists ought to be aware of that.

It’s in that spirit that Dailey undertook the Fenway Rooftop Sessions for the Red Sox with a pilot last season, and in full launch in 2018. “Sam Kennedy saw me playing in Cape Cod. I was opening up for G. Love,” Dailey remembered. “And when I was playing Hot Stove [Cool Music] he said, ‘I know you. I saw you play a couple months ago. I loved your set… Come to Fenway sometime. I want to talk to you about doing something cool, something different.’ And I was like, ‘What?’”

Kennedy and Dailey would come together over a concept that Dailey described as “opening up the community at Fenway to everything that Boston represents.” Kennedy took Dailey around the park to come up with ideas for a collaboration and on coming upon the roof deck (now the vineyard vines club, abutting the Fenway Farms rooftop gardening project), Dailey offered, “There should be a concert series here. I did a little test run of it last summer. This summer I gave them suggestions on who they could get. I gave them thirty acts and tried to represent all the things in town that I love… all the kinds of music.”

“It’s a huge opportunity not only for the artists, but also for the Red Sox,” Dailey continued. “They can be inclusive of everything that makes Boston great.”

At the same time, Dailey recognizes the potential problems of putting smaller independent artists in the corporate complex of major league baseball. “It’s hard to explain to people, ‘Hey, you get to come to Fenway early, go to a secret location that’s gorgeous, hear a concert from a New England artist, and then go watch a baseball game.' But once you’re out there on the roof, it turns out to be one of the best days the artists have.”

Courtesy of Facebook

Just getting to Dailey’s show last month was a synecdoche for that “lost in the corporate world” vibe of the local artists’ concert series. When I got to Fenway—arriving at Gate E as directed—no one really seemed to know where the rooftop sessions were, as I was directed around the entire concourse and up four flights to the Pavilion Club on the other side of the ballpark before finding an usher who could direct me to the vineyard vines club back just a few yards from where my search started. The crowd for Dailey’s set trickled in as he mingled among them, even asking a couple waiting at the bar, “How’d you hear about this?”

By the time he started his set with “It Already Would Not Have Worked Out By Now” from Golden Walker, Dailey played to a crowd that had filled from sparse to intimate, with a clear divide between the rooftop pre-gamers in the corner, and the Dailey fans huddled a few yards away from center stage. It seems the dreams of bringing Boston’s music community into Fenway might experience a few bumps.

As Dailey put it, “There’s a little bit of an authenticity that I have to protect sometimes. I can only make records now with fans and people’s involvement. I love that. But it means I also have to be careful with who I work with. Of course I’d love to work with the Red Sox, but they’re also a big thing. But the way [Sam Kennedy] handles some of the issues that come across the Red Sox desk, I find inspiring. And I’m proud of the fact that he wanted to bring in these artists.”

And Dailey’s thinking ahead with his involvement in the concert series. “Part of my long game is making sure cities like Boston thrive with their music,” he says. “Cities like Boston are going to be in a lot of trouble in five years if they don’t figure out how to protect, celebrate, and elevate modern art forms, especially music. So if songwriters, hip hop artists, rock bands, and indie artists can’t thrive in cities, in Boston, in Chicago, in Seattle, in San Francisco… culture’s going to drop. You need popular art forms to thrive in every major market.”

Given the shifting avenues to make a living as a working-class artist in a city like Boston, there are going to be some adjustments to opportunities for live performances, just as Dailey sees the need to make adjustments to recording practices. This partnership with the Red Sox might strike some as making for awkward bedfellows—massive MLB franchise and hustling local musician—but Dailey sees it as the necessity of behemoth institutions in Boston reckoning with, welcoming, and celebrating what would happen anyway. “Art finds a way no matter what. And it’ll find a way away from you if you don’t have culture… so I applaud the Red Sox for creating opportunities like this. And I’m determined to make sure opportunities like this continue in Boston. I’m from here. I believe in this city.”

Even if not all of those opportunities are necessarily those you can bring your kids to.

Golden Walker is available now. Learn more about the Fenway Rooftop Sessions at