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Q+A with LEAF Singer-Songwriter Competition Finalist Stephen Sylvester

May 1st, 2022

Who’s over six feet tall, an old soul, and definitely doesn’t have a “V” in his first name? You guessed it—Stephen Sylvester, a down-to-earth country artist whose unique and powerful voice is reminiscent of the great R&B singers of the ’60s. He’s living just like his mama taught him, a true-to-his-roots force to be reckoned with. You’ll want to remember this true Southern gentleman: check out Stephen Sylvester’s new album Let Me Be Strong on Spotify or Apple Music.

NewSong Music: What was your intro to music?

My dad was a prolific Christian singer-songwriter in the ’90s, so music was a part of our home from my earliest memories. That plus all the Disney movies meant young Stephen sang A LOT, but my musical awakening happened because of Stevie Wonder, oddly enough. I distinctly remember hearing him sing when I was about 7 or 8 and thinking “I’m going to do that one day.”
What is the first song you wrote that you were proud of, and why?
That would have to be “I Promise You,” which is the song I submitted for the contest (how poetic is that?!). It’s one of my oldest songs that I’m not embarrassed to play, and it was the one that caused my first experience moving an audience emotionally. I played it for folks I didn’t know in a wine bar years ago, closed my eyes for most of it, and when I opened them everyone was crying. After that moment I figured I didn’t have much choice but to be a songwriter.

What instrument do you play, and why?
Full disclosure – I started playing acoustic guitar at 16 specifically to get a girlfriend. It didn’t work, but I fell in love with music instead! My first instrument was actually drums, and that’s still my favorite one to play, but it’s hard to be a solo performer (or get a girlfriend) as a drummer.
How did the pandemic impact you as a performer, for better or worse?
Ooof, yeah the pandemic was rough for me as I know it was for all performers and gig workers. I had about four solid months of no gigs whatsoever, and then opportunities to play started coming back slowly. Today, two years later, I’m only just now back to what I would call a regular performing schedule. The benefit, though, was that all the extra time meant way more opportunities to write, so I write and virtually co-wrote songs like a madman! And I can credit the pandemic for helping me become a much better writer if we’re talking silver linings.
Does the place you grew up inspire you as an artist? If so, in what way?
Yes absolutely, I think Coastal Alabama is about as inspiring of a place to grow up in as a kid could ask for. Scenery-wise it’s full of gorgeous beaches and wildlife, which have been a great source of visual inspiration for me. It’s also still a developing area of the country, so if as a kid I didn’t experience hardship directly it was right there in front of me. And drawing from those stories has been just as powerful of a songwriting inspiration for me as my own experiences, if not more.
In what ways does the craft of songwriting still surprise you?
The magic!! I’m the type of person who wants to over-analyze and really dig into how things work so that I can improve. But songwriting really doesn’t work like that. You get better by practicing and try new methods and know how rhyme and meter work, but there’s still something unquantifiable about writing a song. Which, for me, can be frustrating, but it’s also incredible to experience in real time – songwriting is literally magical.
What are some of your creative goals for this year?
Well my goal every year is to get George Strait to record a song I wrote for him (haha) but I’m also actively playing more regional shows now that the world seems to be opening up for music again. My manager and I are pitching songs to publishing companies trying to get me a deal, and I’m still writing and performing all the time. My unrealistic goal is to quit my day job and do full-time music by the end of the year, and who knows? I’ve been pleasantly surprised too often to think it’s impossible!