Prolific and musically active over the last two decades, acclaimed Boston indie singer-songwriter Will Dailey can still find a way to hide in plain sight.
Maybe not in the New England area, where he’s still based and has ‘local hero’ status (and where he’s earned eight Boston Music Awards and counting, plus has a #1 album [2018’s Golden Walker] on Billboard’s Northeast Heatseekers under his belt), but in other parts of the country, where his music has been heard, without maybe the realization of who it was.
From his 13 million+ Spotify streams, enough songs featured on TV’s “NCIS” to have them considered a recurring guest star, and even appearing on camera to sing on “CSI-NY” and the soap opera “As the World Turns.”
His folk-rock sound can lean toward a nostalgic vibe, while still staying musically current, and can sonically range from a laid-back intimate hush to a larger, widescreen sound, sometimes within the very same song.
The musical troubadour is on the road again, on the second leg of his “Ten Dollar Song Tour”, in support of The Wallflowers for this run, stopping by The Uptown Theater in Kansas City on Wednesday, August 17.
The tour name springs from Dailey’s latest innovative idea and a brand-new song, inspired by the vinyl artwork and song “Clouds” by Joni Mitchell, and is a seven-minute love letter of admiration to Mitchell, only available to be heard at the merch table at Dailey’s shows.
Fans pay what they like to listen to the song on a (we’re not calling it ‘antique’ because that shows our age) Sony Discman, before or after the show. Accompanying it is a journal with artwork, lyrics, and credits, and listeners are invited to leave their name, date, place, any reactions, doodles, and random thoughts. Dailey developed the DIY post-pandemic idea as a project to better connect with each listener, instead of randomly releasing the song into the digital abyss.
Through the magic of the interwebs, we had the opportunity to ask Dailey a few questions ahead of his KC appearance and were pleasantly surprised to find his answers as well-thought out and as revelatory as the care and effort he puts into his own songwriting.
WHM: Tell us about your newest song, "Cover of Clouds" and how Joni Mitchell has been an influence in your own songwriting?
WD: It’s not uncommon for Joni Mitchell to be an influence on a songwriter – I am always pulling from her, especially when I need to check for a healthy level of irreverence to any kind of process.
This song “Cover of Clouds” came literally from the painting that she did for her album Clouds, which I wasn't aware that she did the painting for the cover. Though the album was a part of my life since childhood as it was bestowed upon me by loving adults as an important piece of art. And those moments are really important in someone's upbringing, certainly for someone who ends up doing music for their life.
Somewhere in all that this song poured out, and I ended up using it as a personal check point during the pandemic. Once we could be in the same room with masks and recording studio I got myself, Dave Brophy, Jon Evans, who is the bass player for Tori Amos for a long time, at Jon’s studio on Cape Cod. It was the first time people could be in that kind creative space with masks on, and I just thought this is a healthy song to dive back in after such a challenging period for everyone. And I approached it as if I was just recording a song for my own mental health and greasing my own wheels with no intention of ever releasing on my mind.
$10 Dollar Song is described as a project created with the intention of prioritizing human connection over algorithms and analytics- How do you think Artificial Intelligence and related, will affect Art in general, and songwriting/music specifically?
Art has been interrupted since the beginning of time. We sang around the fire and used animal bones for drumsticks. And then someone maybe carved a drumstick out of wood. And someone strung a piece of intestine as a string to another stick and started the first upright bass. And everyone who played the bones was really upset. It disrupted everything. And my job is not to chase the disruption or be the disruption. For me personally, it's to instill that ancient role of connection and honesty through art. That is how I think of “the job”.
And it can be in the smallest way, and it can be in the grandest way. I've hit a point in my life and career where I cannot measure the difference between one person and 10,000. A million spins, to one person having a sincere emotional reaction to a performance or a song. And AI is going to do more than we imagined and less than we imagined. It's gonna have negative consequences. And it's gonna possibly have some positive results. Maybe it will free us up – we don't belong on a factory line, sitting all day. We don't belong staring at a screen all day.
If we are freed up, maybe we can return to that fire, and we gather around a little bit more in the fields and maybe to our Earth. So, I can't answer, I don't know or worry myself too much about all those questions. Because I'm focused on what my job is. And that will never really change. And if robots take over, and they all look like Arnold Schwarzenegger, we're still going to need artists in the bunker. To sing at the end of the day after we killed a bunch of Arnold Schwarzeneggers.
You've shared the stage/studio with numerous legends- John Mellencamp, Roger McGuinn, Willie Nelson, Steve Earle, and even Stephen King- does any one story or lesson learned, stick out over others?
I think my experience with Eddie Vedder definitely sticks out more than any other cause it's based exclusively on music and seeped in a person I looked up to probably the most. Not only their music, but their ethics. And upon meeting him, I was playing on stage playing music with him within 15 minutes. It instilled confidence in my musical judgment and in who I have looked to for guidance. Which is a lot of what “Cover of Clouds” is about. 
I think that people who do this, especially now when we're in this tyranny of content, and we really don't need new songs delivered to us –100,000 songs come out a day, humanity doesn't need new songs coming at them.
So, you can end up kind of questioning what the hell you're doing with your life, right? So, for this really natural experience to happen, and upon working with this artist and meeting them in person – to immediately take off in a musical direction that was very natural instilled a sense of confidence in my choices and my judgment.
I've kind of existed outside the industry of music, and there's no reason for some of these people you mentioned to work with me. I'm not coming up the charts or anything, I'm not a household name. And so, I’ll always be grateful to someone like Eddie Vedder or Mellencamp, and McGuinn, Tanya Donelly, Steve Earle, Stephen King for all these moments that elevated my artistic experience
What's the best thing about Boston (other than the Food- fresh seafood, great Italian)?
I think the people that I look up to here musically just communicate so much authenticity because if you're called to this path to make it the output of your life, I believe everyone has a song in them but people who have multiple songs in them have some lovely wires crossed, and to operate that calling out of Boston communicates a sincerity that I hear in other non-music biz cities too, but it’s something you have to sometimes hunt for it the Nashville's and LA's and New York's.
If you meet a lifer from Boston, whether it be Duke Levine, who's an amazing guitarist and out with Bonnie Raitt right now or Kevin Barry who is out with Jackson Browne, friends like Tonya Donelly, the hip hop community here, with Latrell James, Oompa and STL GLD, it just feels you know what's going on in Boston and you get to some real soil. It's so so rich, and way more interesting and dynamic than seafood or sports.
You're currently touring with The Wallflowers- have you known Jakob Dylan previously, and what can audiences look forward to?
Jakob is just one of those guys who's been amazing to me. And, like I said I have a scrappy, independent career, and add him to that list of monumental people that I have these opportunities with. I've been doing this a long time, I've never even had an agent, and I kind of love that. That's another very Boston thing to survive that way.
I'm heavily influenced by Jakob, he’s just such an amazing songwriter. The band is ridiculous, his new album is one of his best. I love this audience. I've done a couple of rounds with them; this will be my third.
If I’m out with them in New England or the East Coast a good portion of the audience might know me, but in the mid-west- I don't know how many of those audience members will know me. But I know I'm walking out to a room of people who love songs. They're not expecting, “A show” they want songs to come off that stage. That sounds like an obvious statement, but with so many concerts with backing tracks, lights and a social media element… I don’t know that it is that obvious. And one of my favorite feelings is walking out into a full room that doesn’t really know who I am yet and then I get to play that first song to introduce myself.
Music can do so many powerful things. I just have songs. That audience is looking forward to songs in the songwriter. We do have a culture where a lot of tracks are being made by a wonderful collection of people. And you'll see this big hit with 31 writers, it's not a bad piece of music at all. I’ve listened to some people lament the amount of writers but that fire that we talked about, might have had 31 writers around it, all hitting bones on a piece of animal skin. And then once that wound down, one person got up and maybe did something before in the middle of that. All these practices are ancient, none of it is a new thing. We are just new people experiencing it through each other. And that Wallfowers audience is always waiting for those moments.
Thanks to Will Dailey for taking the time to answer our questions so perceptively and catch him on his 10 Dollar Song Tour, including Aug 17 in Kansas City with The Wallflowers.
Also check out just-released Season Two episodes of the iHeart Podcast he hosts, Sound of Our Town, which is a travel series that happens to feature the music of a spotlighted city and its influence in defining that area’s culture.
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