Will Dailey is one of the most recognizable and beloved musicians in the Boston scene these days. His string of awards at the Boston Music Awards is pretty darn long – very impressive. His songwriting and strong performance skills are what keep people coming back to hear him time and time again. Will has a big heart and is often seen contributing his talents to a variety of great charity events. He touches everyone he meets with his catchy songs and gracious personality.
Check out his website to hear some of his latest music.
Enjoy this video of “Sunken Ship.”
Your music is often described as the kind of music that we used to hear on AM radio. Do you feel that’s a fair representation?
When people describe the kind of music they are hearing to the person who wrote and recorded it that songwriter is learning something about that person. Nobody knows the song and recording better than those who made it. There is, for me, this ancillary enjoyment that comes with hearing what other people think of the song. Having the song described back to me. The good and the bad. How they classify it. What stood out to them. I feel like you get to know that person just a little. If there is continuity across different listeners it can certainly be enlightening but more often than not, if you are truly being honest in your music, it is acute and unique to that listener. It is a form of entertainment for me in a way to get this feedback but also part of the challenge when you are making art. So, I’m not as concerned with descriptions being fair as I am with someone even bothering to passionately describe it.
Where do folk, rock and pop intersect? Are there other musical genres that we could add to your own unique musical Venn diagram?
I just want to be free to make whatever I want and not worry that as a songwriter the idea of a genre will precede my next song. It can be exhausting to think too hard about genre because everyone has their own interpretation them just we have our own individual thresholds for spice.
So the story goes that you’ve been playing guitar since you were 12. Were you self-taught or did you take lessons?
I started with some lessons but then mostly self taught. If I had more time now I’d be taking lessons.
What kind of music did you gravitate to? Did you hear bands and try to play their songs?
Good songs go a long way. Great recordings also go a long way. When they go long together it is crushing and blissful. I’ll gravitate to any of it. On the turn table pile right now is Damien Jurado, Roy Buchanan, Bob Carpenter, Hallelujah the Hills & Neko Case.
What were your first public shows like? Were you solo or did you play with a band?
I played rhythm guitar in a band and sang back up. Mostly after school somewhere, garages and any school event I could get into. Thankfully I didn’t worry about being good at first because I wasn’t.
Tell us about your Torrent project. What was that about and what inspired you do think outside the box for this particular project?.
At that time I was anticipating what it would be like to put out another full album. My last album, Back Flipping Forward, we toured on and did press and radio stuff for a long time. Three years into that I was talking about something three years old. This I suppose goes back to just wanting to be able to make whatever I feel compelled to make but I wanted to make recordings as I progressed as an artist. So we did one EP at a time and then released a package of them at the end. That kind of thing is far more common now. It also ended up being a smorgasbord of songwriting instead of a singular album vision. We had all these amazing guests too because we were so flexible with getting the EPs out that it allowed more time to ask people. T Bone Burnett executive produced with his CODE mastering, Roger McGuinn played on it, Kay Hanley and Tanya Donelly sang on it! So much gratitude for everyone who worked on it top to bottom.
Your last recording, National Throat, was produced with the help of a Pledge Music campaign. Was that a scary and challenging process for you?
I see no other way to make an album spiritually. You can be on the side of artists taking bank loans or be part of making art. But yes, I’m always scared.
You’ve made several cool videos. Do you come up with the storylines or do you work with your video producers?
Some of them I do like “Sunken Ship” and “Higher Education” and then others like “Castle of pretending” the director, Zak Powers, came up with. I got video ideas like I got junk mail but I hate spending time to make them. On the next ones I’ll hopefully get someone to play me.
What’s in store for you in the near future?
If I continue this lucky streak, I’ll start a pledge music campaign for a new album in the new year. Till then I have some singles to get out before that and shows to play. Pay some bills, make new friends, visit with old ones, live healthier somehow, not read too many of those how to fix something in 15 steps and fight fear.