Singer-Songwriter James DiGirolamo Taps Into Classic Pop Roots

During the course of a career that stretches back to the late ’90s, Nashville-based musician James DiGirolamo has worked with Mindy Smith, Holly Williams, Peter Bradley Adams, Alice Peacock, Robby Hecht, Fognode, the Bittersweets, Judson Spence, and many others. Now, he’s finally establishing himself as a singer-songwriter in his own right.

His latest album, Paper Boats, features songs that have a classic, natural feel to them. “The Girl Who has Everything,” one of many album highlights, features a somber piano melody as DiGirolamo explores expresses his feelings of love and devotion. A co-write with Daniel Tashian, the tune possesses a Burt Bacharach feel. “Top of the World,” a song DiGirolamo co-wrote with Robby Hecht, features some terrific electric guitar work.

DiGirolamo spoke to us via phone from his home outside of Nashvile, where he was editing a music video for his new single, “Top of the World” and “pushing my 5-year-old computer to the absolute breaking point where it might have a meltdown,” as he put it. 

Talk about your background. How’d you first get into songwriting?
I never set out to do it. It all kind of happened accidentally, as many things do. I thought I would be a composer or a film scoring guy or something like that. I went to college as a piano performance major, but I don’t think I was going to set the concert stage ablaze with my classical playing. I was very focused on doing instrumental music and moved to New York and I got a few things on television here and there. It was mostly work for hire. I moved back to Nashville. I knew the city to some degree from my four years of college. I had a bunch of friends here. I discovered I could be in a band. That was fun. I played in a band with some guys. Though I never set out to do it, I have always had Paul Simon, the Beatles and that stuff from childhood as something that struck me, but I didn’t think it songwriting something I would be able to do. I tried my hand at it and was really, really bad at it for a long time. It’s a mystery to me how I have become a not-bad songwriter. 

You played mostly in pop and rock bands in Nashville?
Yeah, mainly. And then there was this writers’ night that started in the 2000s. It was Daniel Tashian, who has gone to become a pretty big producer, and Sarah Siskind and this guy Millard Powers who’s a great bassist who used to play with Ben Folds and is with the Counting Crows now. Somehow, I was there. It started at a coffeeshop and grew and had to move to this club called 12^thand Porter. Slowly, that writers’ night turned into a band showcase thing. From week to week, we would sit in and play with each other. Most of it wasn’t country. It was mostly pop and rock stuff. There were all kinds of people come and going. It was a blast. It was a fun time and a really creative time. 

You’ve put out records prior to this new album.
I put out a few things. A couple of years ago in 2018, I put out Lullaby a Black Sheep. I have been trying to figure out what I’m doing artistically, but I’m happy with how that one came out. Prior to that, I had been toiling in obscurity. I hope to change that. I really like that record. I made it with Lex Price, who is a great producer. Anything I got to play on that was cool at all was due to Lex calling me for keyboard stuff. I rang up Lex and asked him what he thought. I had some stuff I recorded at home and wanted to add other instruments. I said, “Should I burn the tapes or should we work on this?” I put that out and was gearing up to start playing my own shows again after a long, long hiatus and then the pandemic struck. I just got this guitar and had a nice pickup installed and was practicing every day. It was like, “Now what?” 

And at that point, you decided to work on Paper Boats?
The thinking there was that I forced into this weird spot along with everybody else. I had been writing a lot and co-writing with people. There was this little handful of songs that kind of cropped up. I don’t want to make it sound like they were connected sonically or they had some lyrical through line. It was almost the opposite. They were pretty diverse. I wanted to see if I could make something out of them right away. Maybe it was a bit of impatience on my part. I wanted to put some other instruments on this and started calling people. That’s how that came about. 

How’d you come up with the concept of bookending it with “boat” songs?
I don’t know. I think I let the music tell me where to go. The name was just a lark. I just liked the sound of it. That was just a playful thing.

Did something in particular inspire “Same Boat,” the first song?
That’s a pre-pandemic thing. It’s funny how events can make you reflect on a lyric completely differently. I started playing that tune one day. This is how my writing process happens. I’m sure it’s not any different for anyone else. You sit down sometimes and play something and mess around and it’ll go nowhere and you won’t have any lyric ideas. Other times, you sit down and play something and it comes right away. It’s a great feeling when that happens, and it’s hard feeling to explain. I think it only happens if you have gone through the process when things are not flowing. If you sit down and make yourself write a song long enough, then this can happen. I had this music that stylistically seemed different. Then, the rhyme came. I thought, “I’m writing this trite simplistic little thing.” But I thought, “You know what. I’m doing it.” I don’t need to answer all the world’s problems in one song lyric. I just wanted to write this happy sounding tune and let it be, and that’s how that came about.

“The Girl Who Has Everything” dates back several years. 
It’s another example of how things happen accidentally and weirdly. That song I had tried to figure out how to record for a very long time. I took a couple of stabs at it, but I couldn’t pull it off. A lot of that is completely my fault. You play it at this tempo or that. You add this instrumentation or that. For whatever reason, I just wasn’t happy. That was a session I did in 2019 in August. I did that during the same session as “Top of the World,” which is out right now. I always loved that song, and I had a chance to make it work finally. I’m so happy that we recorded it. I was possibly a little afraid that it was me coming out of the woodwork with my Daniel Tashian co-write. I worried about how it might go over, but I didn’t want that to stop me. It’s a great song. I couldn’t believe it took so long to get it out, but I’m happy that it turned out well. I bounced it off of Daniel, and he said he liked it and is digging it too.  

Do you see yourself as more of a singer-songwriter or someone who fits into the alt-country scene?
It’s terribly hard for me to answer those types of questions. I’m not opposed to anything. As I get older, I have friends who will talk about how much they hate certain types of music and complain that nothing good comes out anymore. It’s easy to see why people do that. I used to be like that. It’s easy to see why I did that. These days, I feel more accepting of things. If something comes out and it’s not my cup of tea, I feel like it’s a waste of energy. I would be thrilled to have a big superficial pop smash. That would be fine by me. Maybe someday.

As far as labels go, I have just thrown out my militant thinking. It doesn’t mean that much to me. 

You hope to tour behind the album?
I hope so. I’m taking a cautious approach. I think things are heading the right direction [in the wake of the pandemic]. I want to concentrate on playing some shows. It feels a hair shaky to me, but I think we’re heading in the right direction. 

Do you have a band?
I think I would start with just myself. I’m not known as a songwriter. I’ve played on a few records here and there that people have heard, but it’s easier to go out and do it yourself. I’m not going to be headlining. I’ll try to get as many opening dates as I can. I think that’s the way to do it. I don’t know if I’d take piano or not. I’d probably do most everything on guitar to start out with.