After becoming the first artist signed with the resurrected CBS Records and spending two years stumping for his last album, Back Flipping Forward, Boston singer/songwriter Will Dailey is riding into 2009 guns blazing, with an ambitious commitment to release four separate EPs over the course of the year. After his performance on the Late Late Show with Craig Ferguson, Dailey sat down with MetroWize to discuss writing, the Internet, and how to break up with a band you’ve been with for too long, among other things. Coming up Will Dailey will tour to World Cafe Live in Philly, Mercury Lounge in New York City and the Boston Harbor Boat Cruise in Boston - look into buying tickets for his shows here.

How did you decide on the schedule for your EP releases?

WD: I put out a record called Back Flipping Forward, and then CBS Records picked it up, and the time between actually recording it on my own, it getting re-released, doing promo for it, going on the road for it, 2 years passed. I wasn’t able to release anything. It wasn’t conducive to being creative. I thought, “What would make me happiest? What would be best for me as an artist?” and I walked into my record label and pitched it. Not only as that, but as, “This is kind of the way people digest things nowadays. Things go really fast, so why not just kind of ride that rollercoaster?” So it was about serving myself as an artist and being in the present as far as the industry goes.

How has it been working so far?

WD: I think it’s been working great. Maybe it’ll start a trend. It has been one of the things that has caught people’s eye about the project that gets them to listen to the music in the first place. I also wanted to do it for my fan base. I wanted to give them my actual experience of writing songs. I think too often with our modern technologies, we end up saying, “I’m getting out of the shower right now,” instead of giving a real piece of yourself.

Human interaction is suffering a little bit.

WD: Yeah. And this is my human interaction – making music and giving it to people.

Have you ever considered some kind of system where you incorporate fan feedback?

WD: I definitely like doing that with set lists, and since there’s so much material now – I have three records out – I was thinking “Give me your playlist.” Like, “This is the playlist I paint to. This is the playlist I get speeding tickets to.” I’m getting suggestions all the time from people on what I should do next, and that’s really exciting. There are all these little things I never quite thought about. I just thought, “I know I can write the songs.”

You’ve said that you figured out how to make music without a label. How has it been working with a label?

WD: It’s been great, because at this label, even though it has a big name, there are three people. I can get anyone at that label on the phone at any time, and I get to walk in and pitch my idea. So that part’s been seamless.

Which musicians, dead or alive, would be in your all star fantasy band?

WD: I can answer this question for days, but as of late I’ve been obsessed with Stevie Nicks. Elton John’s not far from my mind, and John Lennon’s not far from my mind when I’m writing songs. Elton John because of just being able to rock out a tune, and then sing just a wonderful ballad in the same album or same show. A lot of woman singer/songwriters have been on my mind lately. Neko Case. I’ve been listening to The Globe Sessions by Sheryl Crow a lot for the way it sounds. Joni Mitchell. Carol King. And there’s this woman from the '70s, like remember Boogie Nights? That song, “I got a brand new pair of rollerskates.” Melanie. I love her. I love her. One of my favorite songs of all time, “Leftover Wine,” is a song she sings.

Are you going to try to work with any of them?

WD: We’ll see. (laughs) I guess I have some phone calls to make.

You’ve also said that you played for too long in bands with people that were friends but didn’t share goals with. What finally prompted you to get out on your own?

WD: I started making Goodbye Red Bullet while I was in other bands on analog tape with no computers at all, and had a blast. As soon as I put it out, it was an immediate change in how my music career was going. It was well received by fans and by music reviewers, and XM radio started spinning it a lot. I never really thought to go out and be “Will Dailey.” It just kind of happened from making a record about facing myself as a musician at that point. It carved the path.

Were any of your collaborators on By the Blue Hills (Torrent Volume 2) former bandmates that you broke up with?

WD: No. Those are all luminaries. Whether it be Elliot Easton from The Cars or Kay Hanley from Letters to Cleo, or Tim Brennan from The Dropkick Murphys. That was just about reaching out to some of the people that inspired you.

What would you be doing to survive if you weren’t playing music?

WD: I don’t know. I’m sure I’d be doing something with music. I’d always be writing, so I’d have to find something that allowed me to write and record my music at home. I like working with dogs (laughs). Maybe something in that area.

Do you have any writing or performing routines or superstitions?

WD: I guess my only superstition is not to think about it too hard, not to answer that question (laughs). Live life. You get asked to do a lot of crazy things in this business, and I’m always up for trying anything new, because song writing’s about translating experiences and feelings and thoughts, and the more experiences I have, the more feelings I have and the more life I’ve lived. It’s a life rule – just say “Yes” to new things.

What’s the best thing that you’ve said “Yes” to in the past year?

WD: Farm Aid. Getting to play with Neil Young and John Mellencamp and Willie Nelson, Dave Matthews. You’re hard pressed to find something that really makes a difference. Farm Aid definitely makes a difference. It faces the root of a lot of our problems head on, so being a part of that was incredible. I got to stand on stage with Willie Nelson at the end of the night. I got to just sit on the side of the stage and watch Neil Young. That was mind-boggling. I got to see all these wonderful people.

Was that your favorite recent show?

WD: I don’t pick favorites. There’s a lot of them so it kind of blends together. I played in my friend’s living room recently and it was one of the best nights of my life.

When did you first start making music?

WD: I played trumpet and violin and piano, and I was always avoiding the lessons, just making noise, making my own sounds. I first got my guitar at age 12. I soon thereafter started recording it into one of those little recorders. I just recently found some of those old tapes, and it was horrible and endearing. I think it was good to have found them. I’m pretty sure it was good (laughs).

Did you experiment with other genres? Did you have a glam rock band at some point?

WD: No. I’ve always played a lot of acoustic music and rock and roll. Sometimes I’ve been in heavy bands. One of my favorite bands is Fugazi, and I had a band where I just wrote like I was trying out to be in Fugazi, but there’s always a thread through it all. That’s been nice recently to see the thread, and kind of grabbing it and directing it instead of just throwing things at a wall.

Sort of coming into your own as an artist?

WD: Yeah. I think walking into my record label and saying, “Here’s how I want to put out my music” was the beginning of that.

Is the Internet the next great hope for music, or is it a little over-hyped?

WD Look, if you drink too much water it’s bad for you. I believe the same goes for the Internet. It can serve a wonderful purpose, and for art it gives everyone a shot. There are more people out there who are having careers and putting out the music that they want. At the same time, I see a lot of musicians spending too much time online writing a blog about what they’re doing before the show they’re about to play, and what kind of tea they’re drinking. You’re asked to do so much more as an artist, all these different kinds of mediums for promotion, when the most important things is just to be true to your art.

What’s your favorite record that you own on vinyl? Maybe top 5?

WD: I got this really pristine copy of Morrison Hotel by The Doors that I always loved. This band Midlake. They’re out of Texas. I think they’re just phenomenal. And Apostle of Hustle. Those are two new bands that I love and they come out on vinyl. I’ve got an old Melanie record. Bitches Brew by Miles Davis is great on vinyl. Fugazi’s End Hits album I found on vinyl. Some Beastie Boys records. I had a roommate a couple of years ago that had a wall of vinyl, so I was spoiled.
What do you find inspiring about Boston?

WD: My roots are there, and our country started there. Traveling the country when you set out from the root - to go out and see the result and then come back - all my experiences there, being by the ocean. I love the state of Maine, so I’m close to there as well. For me it’s somewhat out of the madness.

If you could be any animal, real or fictional, which would you be and why?

WD: My friend Gunnar – who made the artwork for Back Flipping Forward – made me these great sneakers. He asked me this once and I said, “I’m torn between a hummingbird and a puma,” so he made a hummingbird shoe and a puma shoe for me so I could decide on each day which one I was going to leap from.

How long does it take you to write songs? Torrent 1 & 2 is kind of about people seeing your songwriting process, but how does it really go?

WD: Well sometimes it’s five minutes and sometimes it’s five years. There’s a song on Torrent Volume 2 called “Love Is on the Way” which is just kind of a fun romp about a middle-aged, overweight man waiting for a mail-order bride (laughs) and that took me a minute. I knew the story immediately. I could just see this guy preparing for this woman. And then there’s a song that I hope to get on Volume 3 that I’ve been working on for three years. I just try and always keep the window open because you never know when it’s going to come in. “Peace of Mind,” the lyrics came out in 5 or 10 minutes. That opening chord progression though, I was playing for two years and just waiting, and letting be. That’s maybe one of my songwriting rules – I don’t force anything, but I do work at it. I try not to judge myself too much, and have fun.

When are you going to start recording again?

WD: Hopefully August. I’ve been demoing up about 5-8 songs that I’m really excited about finishing. There’s one song on there though that I’ve been working on for like, three years, waiting for that last piece of the puzzle. That’s usually it, the last piece.

The “Aha!” moment.

WD: Yeah. The third thing.