Country singer-songwriter Jimmie Allen continues to expand his musical journey with the release of two new singles, Live Another Day and Drop It Like a Tailgate. Known for blending traditional country storytelling with a modern pop sensibility, Allen reflects on the personal moments that shaped his music, including the loss of his father in 2019 and memories of his hometown of Milton, Delaware. In this interview, he also discusses his path to Nashville, collaborations across genres, and what it means to see his music reaching audiences around the world.
Your new songs “Live Another Day” and “Drop It Like a Tailgate” carry very different energies. What does each one represent for you at this point in your career?
Live another day is a constant reminder for me to always fight to make tomorrow better than today. When I lost my father in 2019 my world was crushed. The support of my friends and family keeps me going. The phrase keep going is whst comes to mind every time I hear or sing that song.
Drop it like a tailgate gives me home town summer feel good vibes. Where im from when summer rolls around we drop the tailgates on the truck, open a few beers and take life slowly .
From the beginning, your music has blended traditional country storytelling with a modern pop energy. How do you balance honoring the genre while still pushing its boundaries?
When creating my music I never think about a genre past or present. No matter the genre they all have a history that has been built my artists before. I just focus on the song im writing in that moment. The only thing that goes through my mind when I’m creating is: do I love it? Do i trust it? This is what feels right to me. As far as genres go , i dont think about them. I only think about the music. I just create and i let other people determine the genre.
Your journey to Nashville required years of persistence before your breakthrough with “Best Shot.” Looking back now, what was the most challenging moment of that path?
There were a few challenging moments, one was living in my car for a couple months. I think the most challenging was just remaining patient and staying true to myself through my music. Never focusing on what other artists were getting opportunities when I wasnt . My parents raised me to never be jealous of someone else’s success. Seeing other artists I know get record deals only motivated me to keep going.
Many of your songs carry personal stories and references to your hometown of Milton, Delaware. How do your roots continue to shape your songwriting today?
My hometown raised me and no matter what the songs are about my perspective comes from how and where I was raised.
Throughout your career you’ve collaborated with artists from very different musical worlds, including Brad Paisley, Noah Cyrus, Nelly, and Jennifer Lopez. What do you enjoy most about working across genres?
Working with other artists across different genres is one of my favorite things. I get a chance to learn how they process songwriting from their experiences. For me its educational. Learning is something I have always loved.

Country music has been expanding globally in recent years. What does it mean for you to see your music reaching new audiences in places like Brazil and the United Kingdom?
It’s incredible to see my music travel beyond the small spaces and places where I create them. It further promotes the idea that we are a lot more like than different. Seeing songs I created in my hometown connect with people in Brazil and UK is a magical thing.
Beyond music, you’ve also appeared on television, from hosting award shows to participating in music programs. How have those experiences influenced your perspective as an artist?
Stepping outside the music world I get a chance to meet so many different kinds of people. It also gives me a chance to step into other things I love such as hosting, stand up comedy, acting etc.
Looking ahead, what kind of story or message do you still feel you haven’t told through your music yet?
I feel like I haven’t really told the story of personal heartbreak. Who knows maybe thats something i will write soon.
Follow Jimmie Allen on Instagram
