5 Q&As with Drew Holcomb, ahead of his show at World Cafe Live on Oct. 23.

Even when singer-songwriter Drew Holcomb isn’t wearing a hat on his head, he’s still donning figurative ones.

For instance, he's the leader of his namesake band (Drew Holcomb and The Neighbors). He’s the founder of the Moon River Music Festival, an annual affair held in Tennessee. Holcomb also is a husband and father. 

Audiences will get a chance to see Holcomb sporting his musical cap when he and The Neighbors tour to the World Cafe Live in Philadelphia with the new album, “Dragons,” on Wednesday, Oct. 23.

Holcomb dished on the meaning behind “Dragons,” grieving the loss of several loved ones as a young adult, and his most memorable Halloween costume.

Within your late teens to early 20s, you experienced a lot of loss. How did you manage to cope with that, Drew?

I am not sure anyone that young manages it all that well, but music was a big part of my grieving process. Music is where I went to feel the pain and remember the joy. Before I lost my brother I was mostly into classic rock like Zeppelin and grunge like Pearl Jam, Nirvana, etc. But after his death is when I really started listening to more singer-songwriter oriented music, like David Gray, Patty Griffin, Van Morrison, etc., and that really started me down a different musical path altogether. 

Why did the title "Dragons" attract you? 

It's a song on the album I wrote about my grandfather. He was a larger-than-life figure... a World War II veteran, a doctor who lived in Kenya for a few years, a fisherman, a golfer, an itinerant preacher and a fantastic storyteller. He was one of the major influences in my life. I wrote this song about him, and played it at a few shows last year before we made the album. The first show we got a standing ovation after the first chorus, and I knew it was going to the be the name of the album. It just seemed to resonate with people. As the old saying goes, “Be kind, for everyone you meet is fighting a great battle.” Everyone is fighting some type of “Dragon” in their life. 

Why was it important to add co-writers outside of the band on "Dragons?" What impact did that have on you? 

I have been making records for nearly 15 years. So I wanted to try something new. I have not done a lot of co-writing over the years and really wanted to take advantage of some of the offers from other artists and friends to write together, with folks like Lori McKenna, etc. I think it stretched my creative imagination, both in terms of melody and lyrics, but also just the idea of what is possible. Sean McConnell really challenged the capacity of my voice on “End of the World” in a way I would never have done on my own. 

Moon River Music Festival includes a lot of talented artists. But how do you walk the fine line of selecting the right performers for the festival?

Well, it is both fun and exhausting. You want a little bit of everything for everyone and that is a challenge, especially dealing with budgets and artists schedules. So I let my partner AC Entertainment do most of the heavy lifting. I just make a dream list and they start having conversations with managers and agents and we talk every couple weeks to see where things stand. I always want to have some of my friends on the bill, and that has made it a lot more fun. 

With Halloween right around the corner, what's one of your favorite costumes you've ever worn or seen? And what's one of your favorite scary movies?

In 2013 in Philadelphia we were actually playing on Halloween at World Cafe, and so the whole band dressed in Star Wars costumes. I was ObiWan. Ellie was Princess Leia, Jon the drummer was Yoda, Rich the bass player was Darth Vader, Nate the guitarist was Luke Skywalker, and our 1-year-old was a wookie. It was a blast. And my favorite scary movie is “The Shining.” It haunted me for years.