CR 023: Will Dailey on Connecting with Audiences While Staying True to His Art
CR 023: Will Dailey on Connecting with Audiences While Staying True to His Art
The Boston singer-songwriter discusses his latest album, “Boys Talking,” and his unorthodox career choices.
Over the course of his 20-year career, Will Dailey has consistently forged his own path. In 2014, the singer-songwriter broke free of his major label contract in order to go the indie route. In 2023, he launched a “$10 Song Initiative,” enabling attendees at his concerts to pay $10 (or however much they can afford) to listen to a prerecorded, seven-minute, unreleased song—one they can’t hear anywhere else. That project served as a catalyst to his latest release—a full-length album, Boys Talking, which is available only through Dailey’s website, and will not be offered on streaming platforms.
These unconventional decisions, he says, are driven by his desire to connect with listeners on a personal level. “I’m upset about everything that’s going on in our world. What can I do about that? Well, maybe this isn’t the repair or the fix, but it’s one push in a direction that values the human next to the human. It’s just a pebble in the ocean, but what if we all find a pebble that resonates with us?”
A Massachusetts native, Dailey records his music in his hometown of Boston—a decision he made early on in his career. “I got a record deal from an independent company, and they wanted me to make the record in L.A.,” he says. “I thought, ‘Well, I could employ my friends if I do this at home and work with people I really trust.’ And that just started my vision for doing everything out of Boston. Look, if we all moved to Nashville, New York, and L.A. we’d be doomed as a culture. Any small, even seemingly insignificant way I can rebel against that I will, because I have plenty of friends that are counted as corpses in those towns because they gave those towns their dreams.”
Recording at home also gives Dailey access to some of Boston’s finest musicians. Kay Hanley (Letters to Cleo) and Tanya Donelly (Belly) are just two of the many artists who contributed to his 2009 release, Torrent. This year, Juliana Hatfield joined him on “Make Another Me,” the first single off Boys Talking. “The gift of having mentors like Kay Hanley, Tanya Donnelly, and Juliana Hatfield makes the decision to come home and operate out of this town perfection,” he says. “That trio of talent and power for me... I don’t know. I don’t really have the words. And I have to be cool about it, too, because I just want them to think I’m cool and be my friend.”
Dailey and I recently chatted about his creative choices, his musical influences, and what he hopes to do next.
SANDRA EBEJER: You’ve been part of the Boston music scene for a long time. How did your interest in music begin? Were you raised in a musical family?
WILL DAILEY: There was always music. I went between houses most of my life, between families, and different people came in and out as those families expanded, and I got to understand people through the music that they loved and how they related to music. I don’t remember thinking, “Ah! Music!” It was just, music was my way of understanding myself and people. Then my mom ended up marrying a musician, and he had a guitar. I used his guitar as a gateway, but he had a nice guitar, and he’s like, “You gotta get your own. If you get 75 bucks together, I’ll help you find one.” He found one somewhere, used, and thus began my relationship.
You struggled early in your career. You had to sell your car to fund your first album. You went on tour but had appendicitis and no health insurance. You were in debt. A lot of people at that point would have given up on their dreams. What made you keep going?
Giving up kept me going. I was so young when I think of this time, but in my mind, I had been in my college band for seven years. Then I went and made my own record under my name on the side, thinking, “I just need to do this for myself,” because I was really writing songs for them. I was writing songs for those three friends, not for myself.
I dropped CDs of my first record, Goodbye Red Bullet, in the mail, and put one to XM Radio, and they started spinning it on this one channel. And I was stuck being myself. And as myself, I had to go through that whole upheaval of, “This label wants to meet with you” and this and that for two years, to the point of [it being like] this dark, tragic Coen brothers kind of comedy of none of it working out. And living in Los Angeles, getting appendicitis, getting a bill for $50,000 from the hospital, and thinking, “Okay, well, this is just silly.”
In my brain, I walked away from everything. And as soon as I did, the phone rings, and a guy I was working with was like, “I got you this indie investment record deal, and they want you to come back to L.A. and make this record.” I said, “No, I’m going to stay in Boston. Fuck all this.” In my mind I was like, “I’m making one last record with someone else’s money, because I’m broke.” I told them, “I don’t have a guitar to record the record.” That’s the best I could get out of it. They’re like, “Okay. You can go to Guitar Center and use our credit card.” So I got the most expensive Gibson acoustic I could. I still have it. It’s this triumph in my life, where I learned to bend the rules a bit to make sure that I can always do this. And that’s been my business plan—just, how do I get to write and record the next song in the way that I envision? That’s it. That’s my business plan.
And it’s crazy, because just a couple years after struggling to get by, you were signed to a major label, you appeared on CSI: NY, and your music was featured in a bunch of TV shows. What was that time of your life like for you?
That period was whimsical in that I had hit rock bottom, and everything started to work out beyond my control. When I went with my hometown crew in Boston to record Back Flipping Forward, my producer, Tom Polce, said, “My buddy in California is starting up CBS Records again, and he wants to hear what you’re doing.” And I was like, “Man, I’ve heard it all. More of this? Sure. I don’t care. Guess what? It’s not going to work out, because I’ve been on this roller coaster for years.” He sent the tracks to CBS. In the meantime, I put that album out on my own and did some album release shows and was having a good time. I was like, “I got these guys to pay for this record,” thinking I had a final coup. [Laughs] Then all of a sudden, I’m signed to CBS, and I had to start thinking seriously.
One night I played in New York, and I’m getting some air outside after the set, and this guy with tattoos and gold chains comes up to me. “It was a great show, man.” I was like, “Oh, thank you.” “I’m gonna put you on my TV show.” I was like, “Oh, yeah, sure.” Again, like, “Yeah, sure, sure, sure.” Two weeks later I’m at CBS with Gary Sinise sitting in his trailer while he’s making sure he’s playing everything correctly on the bass to my song that he’s going to play in a fictional show where I’m playing myself after he solved a murder. And I’m just so enthralled by the adventure. I’ll say yes to everything once, because if it feeds even my disappointment, it feeds my life and my artistry, and if I don’t like it, I won’t do it again. So it was interesting to get swept up into all that while, at the same time, that industry avalanche was still happening. I mean, that label didn’t last long. They sold me to another one, and I got there, and the two people who signed me to even a bigger label were fired and let go, and then went to run the show The Voice. And I realized, “I’m gonna be a tax write off on this label for the next five years and my nightmares will have come true, not my dreams.”
You’ve released projects in very interesting ways. With Torrent, you put out digital EPs of new music every few months. You did the $10 Song Tour. You have the new album, Boys Talking, which is not going to be fully available on streaming platforms. What drives these decisions?
Well, Torrent came from being on CBS and having released Back Flipping Forward on my own, and then having to release it again and talk about it over and over. When it came time to do my next thing with CBS, I said, “By the time you record something and you put it out and you hustle, it’s like two years down the line, and you’re faking it, because you’re really writing something else.” I was trying to answer my own artistic needs with Torrent, and that was the first time I said, “What if we did it this way?” I put it in a marketing pitch to them while I was taking care of myself, and that really helped me connect some dots to survive. And when I was on Universal, I had to go in and say, “I shouldn’t be here. I’m gonna wither away.” I had to part ways with them. I had to come up with this really soulful agreement with the label to get out of my deal. I went and did National Throat on my own, which turned into, “Guy leaves biggest label in the world to do it himself.” I did the thing to protect myself, and everything worked out better for that record, better than I had on any label. It charted on Billboard, got me all around the country and all around the world.
With the $10 Song, the song is called “Cover of Clouds,” and it’s six-and-a-half minutes. I thought, “If I drop this online, my own mother will get a text message before it gets to the first line of vocal, and she’ll be like, ‘It was lovely. I love it.’” We have access to the world in the palm of our hand, [yet] we’re not really engaging with the world. We’re not getting a true representation of everything. No one’s really running it. People are benefiting from the problem. But I can’t just say, “Spotify sucks” if I’m not willing to say, “How can I add value to myself and you?” Literally you, when I say, “I need six-and-a-half minutes of your time. And I believe it’s important, because I made this.” I’m asking for less with the $10 song project, so that we can each have more.
The reaction is cellularly realigning for me, because I have to abandon all the normal market measurements. There’s no counts, there’s no streams, there’s nobody feeding me texts or posts or shares of this thing. It’s just us. The emotional feedback isn’t a play count, a chart count, or view count or a follower count or sales count, it’s the actual person. Many times, at many shows, the response is some form of, “I don’t think I’ve been listening to music very much, because I gave you $10 to listen to something once. I knew I was listening once, so I told my companions to leave me alone. I put my phone away, and I just focused. I didn’t ask what genre it was. I just listened.” It feels so good. But I’ll be lying in bed like, “Man, I wish I could release ‘Cover of Clouds’ and share it with everybody right now.” You still have that feeling. You want to give it to the world. But when I take that 20th century, capitalistic mindset, and I slow it down and I keep it in its lane, its rewards are continuous night after night after night.
I was like, “How do I do that with my next album? I just won’t release it!” I’ve sold more copies of Boys Talking in two weeks than I did of my last two records in two weeks. The thing about these choices is that they’re connecting me to the people who would enjoy my music before they’ve heard it, if they haven’t already. That’s something that I did not expect, and that’s been really nice.
Juliana Hatfield sang with you on the single “Make Another Me.” How did the two of you come to work together?
Juliana, to me, is a McCartney-level songwriting talent. I was supporting her [on tour] in 2020. At that point, I was a fan, but spending all that time with her show, night after night, and it getting ingrained further and further, you just see the other edges of the talent, and it fully wedges into your psyche. Then her album Blood came out, and I was like, “This is her 19th album, and it’s my favorite one.” So when I had “Make Another Me,” I knew that song needed another voice to help cut it through a little bit. There’s humor in that song in its sadness and its honesty, and I thought another voice would quell some of the loneliness intrinsic in the song, to pull some of that out, like a zest of lemon. And I was like, “Man, it’d be so cool if Juliana did it.” I thought that for three months, and then I was like, “Alright, I’ll write an email.” So I thought about the email for two months. Then I wrote the email for a week and sent her a demo. And she’s like, “I’d love to do it. I love this song.”
Then I’m thinking, “When do I ask her to come into the studio?” We cut most of Boys Talking live in the room, but we cut it without her. I was like, “This song’s just not working. We’ve got to recut it. It’s horrible.” This whole time my co-producer, Dave Brophy, is like, “You want Juliana. Let’s get that, and then we’ll assess.” She comes in, gets on the mic, and I just collapsed to the floor. I was like, “Yes!” That was the vision, and it all came together.
The songs on Boys Talking touch upon isolation. Did you go into this project knowing that you wanted to write about this issue? Or did it come up organically as you were writing these songs?
I had two friends pass away during 2020, one from cancer, one from suicide. They were the friends that, on the morning of the release of a record, when I woke up, there’d be a dissertation in my phone about it from [one friend], the other one I would see on the road. When both those people are gone, you start thinking about all the people that your energy relies on. So it started there, and the feeling of loneliness that comes from that, and of being without and conversations with men, men trying to have conversations and trying to communicate.
I found a post from your website that was written during the pandemic, in which you wrote, “I find myself leaning on the songs of others to cope.” That really gets to the heart of why I launched my Substack. I wanted to talk to artists about the art they turn to when they need inspiration or comfort. So, who are some of the artists that you turn to?
A big one that isn’t mentioned a lot is Joan Armatrading. I love her. I’m often looking to be humbled. Fiona Apple does that a lot for me. Eddie Vedder, who is a friend—I’ve gotten to play with him a bunch—he’s like my spirit animal. I listen to a lot of jazz because it frees me up. If I listen to songs I think, “How’d they do that? Why’d they do that?” I’m constantly re-engineering, reverse engineering. With jazz, I’m just free to enjoy it.
I heard the new album by the band The Smile, the Radiohead offshoot. It blew my mind. So on this whole tour—I just finished two weeks out—I listened to the first five Radiohead records while I was driving, and it was wild, because I’m obsessed with constant growth. That’s why Juliana is so huge for me, or Radiohead or Vedder, or Fiona Apple or even McCartney’s third record and Dylan’s last record. They were digging deeper. I never want a past hit to be the thing I’m known for. I want the thing I made to be what I’m known for. And through all the things that we just talked about, that up and downness, the perceived failure of my career in the marketplace of American music has been the greatest gift, because I’m ripe for discovery. I would run away from, “This is it. Boys Talking is what you’re going to be known for the rest of your life.” That wouldn’t be healthy for me.
You’ve achieved a lot in your career. You’ve performed with incredible artists, you’ve toured the world, and have released critically acclaimed albums, often on your own terms. Is there anything you haven’t done yet, professionally or creatively, that you’d like to do?
I don’t have a big list, other than more of the same. Like having someone like Juliana Hatfield on your record, playing with Eddie Vedder—I’ll do more of that. I would love to play with the Boston Pops. There’s a ton of people I’d want to work with. What I know now is that if you just keep going, magical things happen, so I don’t really need to set too many goals. This goes for all of us. When you think it’s over, if you can take one more step, it’s shocking what might happen. Anytime I get in my wallow, it’s like, if I could just get up and get a cup of water, if I could just open the door and walk outside. You have to allow victory [in]. Brushing your teeth, taking a shower, picking up your guitar, playing a C chord on the piano. Especially since 2020, as an independent artist in lockdown, the things I want to accomplish, [aren’t], “I’m going to do this for an hour a day.” It’s more like, “Hey, you folded your clothes. Good job.” And, “You made a record. You put it out. Great. How many people listened to it? Doesn’t matter.” People I work with say, “How much have you made off that?” Doesn’t matter. Let’s do the next thing. Keep going. Magical things happen.
It’s hard. It’s not easy. America is designed to make you feel like you’re not enough. People come up to me and say some variation of, “I just discovered you. You’re going to blow up!” Or, “I am your biggest fan. I love the new record. I don’t know why you’re not bigger. You should be famous.” Five, ten years ago, I would start making excuses for what I was not to them, or I would feel awful. Now I realize it has nothing to do with me. I’ll say into the microphone, “You need to know that you’re enough. You feeling that way about me? There’s no higher. And no one should rob either of us of that feeling of how you feel about my music and how that makes me feel, knowing that we connected through it. If that’s being taken from us, we’re fucked. So let’s not let it.”
To learn more about Will Dailey, visit his website.
This interview has been edited for clarity and length.
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