11 Questions to a Nashville Musician: Hugh Masterson

Hugh Masterson (Photo by Danielle Holbert)Photo by Danielle Holbert

Fresh off a tour opening for The Bottle Rockets that included a local stop at The Basement, Nashville-based Americana singer-songwriter Hugh Masterson has released a new single, “Trouble,” that is sure worthy of a listen or a few. The song is from a yet untitled LP that will be a follow-up to Masterson’s first solo effort, “Lost + Found,” that he released in 2017. The bulk of the new record was recorded here and was produced by Justin Glasco formerly of The Lone Bellow. 

“Trouble” is a hauntingly beautiful reflective number that as one might suspect, came from Masterson being in a tender place in life as well as having to come to grips with being challenged as a songwriter. “I lost my mom to dementia during the coldest part of the year in northern Wisconsin,” Masterson recalls of the inspiration behind “Trouble.”  “I ended up suffering from a depression I was having a hard time getting out of. I lost a job and a relationship, and I needed a change. I moved to Nashville, so I had to start over completely, and it wasn’t the easiest process for me, having left my band behind as well. In the end, if you keep working through and towards something, a lot comes out in the wash. This song, and the album it comes from, are about trying to get by and to get through the challenges of life and love, and ultimately realizing much of what we try to control, we cannot.”

We thank the “Milwaukee Man” for giving his 11 answers to the 11 questions. You can see Hugh during this years Americanafest on September 11 at 7pm when he joins a songwriter showcase at the Cambria Hotel’s True Music Room.


Where are you from originally, when did you move to Nashville and why?

I grew up in Northern Wisconsin near Lake Superior and lived in Milwaukee for 15 years. I just needed a change and a new challenge, and I already had so many friends in Nashville. Also, winters are cold.

What are the first and the last records you bought, and where did you buy them? Were they CD, vinyl or digital?

First was Taj Mahal’s Senor Blues on CD, and last was Phosphorescent’ s C’est La Vie on digital.

First and last live concerts that you’ve seen? 

First was Bob Dylan in Duluth, MN (although I saw plenty of polka music in the small town that I grew up in) and the last was Tristen (Gaspadarek) in Appleton, WI at the Mile of Music.

Whose star should be added to the Music City Walk of Fame?

Keith Whitley

Where do you go in Nashville for coffee and pizza?

Mmmmm, coffee and pizza, my favorite combination! Caliber Coffee in Donelson and Lockeland Table for pizza.

What’s your favorite record to ever come out of Nashville?

That’s hard for me. Obviously, there’s so many great records, and I have an extremely hard time picking just one favorite.

Where’s the best place to eat late night after a show?

Dino’s, Dukes, and Elm Hill Tavern since it’s open late and close to my house.

The Bluebird calls and asks you to host an “In the Round.” Pick three local songwriters to join you.

Brian Elmquist, Liam Russell and Rachel Kate.

What are your favorite music venues to play in town?

Basement, Mercy Lounge and Basement East.

Name a musician who you’d like to see move here?

Greg Brown

Finally, what’s in your musical future?

Working on finishing a new record. I have ten songs recorded, and we are adding the final touches and mixes!  After the release, I’m sure I’ll be out on the road much more to promote it.



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