Isaiah Bennett

Featured Maine Artist of the Month – Isaiah Bennett

Isaiah Bennett is a Billboard Top 10 country singer/songwriter from Southern Maine. A husband, father of 3, and troubadour. Over the past 10 years he’s established himself playing all around the New England music circuit, opening for big country acts, having some singles on local radio, and continues to do what he loves while still being true to his roots. Isaiah’s unique voice and compelling songwriting, blended with his charismatic energy have helped solidify him in the community as one of Maine’s staple singer/songwriters. If he’s not playing at public venues, you can find him serenading people at private venues, weddings, and charity events throughout the New England area. We had the pleasure of interviewing Bennett & hearing his new single, “Keep Me Company” at our location on Spring Street in Downtown Portland. You can find both his interview & the live video of his new single below!

What Are Some Of The Most Significant Influences On Your Music Career in Maine?

I grew up singing in the church, so there’s a lot of that soulful singing that’s influenced me, but also artists like John Mayer, Coldplay, The Beatles, Keith Urban, James Taylor, and Kenny Chesney. Other than Mayer really, I more gravitate to songs and how they make me feel.

Who Or What Inspired You To Pursue a Career In Music?

I had been playing out in bars/private events since 2008, but it wasn’t until my wife convinced me to do it full-time in 2016 that I made the leap.

As A Musician, What Do You View As “Success” in the Music Industry?

First and foremost, it’s connection. Creating something unique to me (and hopefully to others’ experience, too). Knowing some people get it, or at least get off on it in some way. It’s waking up not trying to go after quick wins in the industry, but doing the hard work of writing and singing songs people love. Having the respect, admiration, and support of my peers and ultimately managing to pay the bills through doing something I love and am passionate about!

Isaiah Bennett Maine Musician Playing Guitar and Singing at Stage

What Are Some of the Greatest Challenges of Your Career So Far?

Not feeling good enough and comparison. Regret for not taking some opportunities that were given to me.

What Advice Would You Give to Someone Just Starting Out in The Maine Music Space? 

Put in the work, connect with other musicians/promoters/business owners, be humble, and always be authentic in your performance and storytelling.

If You Could Be Remembered for One Thing, What Would It Be?

I would want to be remembered as being my authentic self, even if people didn’t want to listen to my songs, that I would stay true to my sound.

What do you think is your greatest success in your career?

Honestly just building my career around my busy life. I have friends that tour full time and are away from their family and miss so many memories they will never get back. My wifeand I have 3 beautiful young children, so Im thankful most days I’m around them until I go to work at night. I’ve built up a very successful wedding business singing/DJ’ing for the past 10 years, that allows us to take time off and travel in the off season.

If You Could Start All Over Again, What Would You Do Differently?

I have a lot of things I’d do differently, but when I had more time when I was younger, I would have put myself 100% in from the start.

What Would You Do To Gain Self-Awareness When Everyone is Out to Flatter You?

I feel like Im my own worse critic haha, so even when the praises come, I remind myself there are so many other incredible performers out there, that are way more talented than I am and more hardworking. I’ve been thankful for all the connections and open doors that have come my way, but at the end of the day I’m just a husband, father, and aging musician in a world full of incredible art.

Isaiah Bennett Maine Musician Playing Guitar and Singing at Stage

Follow Isaiah Bennett Here:


Website | Instagram | Spotify Weddings & Private Events



Staff Writer