Authentic Florida Brilliance: How Ben Prestage rocked my world

I have long grappled with whether I’m an actual fan of blues, honky-tonk and bluegrass. Upon hearing one of the best musicians I’ve heard live in Sarasota last weekend — Mr. Ben Prestage, “One Man Band,” who happens to excel in all three of these genres — I’ve gotten some clarity on my fandom status.

My first encounter with Ben Prestage happened in St. Pete last Saturday, and ended up with me coming back for more here in town at the unique Stragglers Bar in south Sarasota. I’ve come to realize that what makes me love these genres, when I do love them, is not that a particular style of note combinations, vocals or songs are used, but rather, that the musicians themselves communicate the essence of where that style was born. Hearing Ben Prestage not only gave me eight-plus hours of being in love with these genres all over again, but also the precious experience of witnessing true excellence, extraordinary talent, impressive showmanship and just a great, unique human being in full swing.

When I first saw him in St. Pete, I’d been convinced by a good friend that he was a “must-see” phenomenal musician. Skeptical by nature due to my somewhat picky musical preferences, I went up to St. Pete open but not expecting that much. I was also tired from a trip to South Florida earlier that day, and secretly hoping we wouldn’t stay out terribly long. I walked up to a crowd surrounding Mr. Prestage as he launched into a new song … he sported a full beard and a train conductor hat, surrounded by a gaggle of instruments including drums, harmonica and stringed things such as guitar, banjo, cigar box and who knew what else. I was won over instantly as Ben played something jivey that sounded Appalachian. As the night wore on, my respect grew deeper as he performed a wide range of styles from bluegrass to blues and some honky-tonk thrown in.

I’d originally planned to spend the next day at Busch Gardens, but when we heard that Ben was playing Sarasota the next night, the Busch trip got curtailed. We headed to Sarasota’s own Stragglers Bar in the early evening, which I hadn’t heard of until that day. The car population was heavy with motorcycles outside the bar, and it was a pleasure to walk in on a group of smiling, rapt motorcyclists along with other folks who I don’t tend to see in the haunts I frequent downtown.

Seeing Ben play a second time expanded my respect yet again: I had heard a near-full set the night before, and it was two hours before I heard him play something from the night before.

While I’m in no way a musician or legit music critic, I can safely say that Mr. Prestage has a rare mastery of each of his instruments. What makes it cooler, he’s usually playing several at once — with drums hooked up to foot pedals, he strums and sings simultaneously, often with a lit cigarette somewhere within arm’s reach and a harmonica duct-taped to the microphone nearby as well.


It was a marvelous evening. As Ben switched among his various stringed instruments — acoustic guitar to cigar box, cigar box to electric, and on again — he moved through genres with a fascinatingly rugged fluidity. His voice flipped easily from a bearlike, barrel-deep growling tone to soaring high notes, his songs from joking jumpy (a song about moonshine was one of my favorites) to raw, soul-carved, husky blues. In between songs he also went the extra mile, weaving each act together with an entertaining monologue to lead into the next song — “Who here went to the Baptist church this Sunday?”

Days later, I still feel full from this show. What was it? And why do I now rank him in my very narrow list of favorite musicians? What stands out for me in Ben Prestage is what I can only call “wholeness” and “authenticity.”

Here’s my theory. Ben Prestage is one of those musicians who has achieved (or perhaps always possessed) full authenticity. He is real, pure and unrefined in the sense that he’s not trying — he just is. Not to say he doesn’t work at what he delivers — that level of picking, singing and coordination doubtlessly takes hours of solo practice. But it comes out of him with such full force that each of these components, and the magnetic whole package, are merely an expression of a core that is very deeply anchored in the creative spirit. However hokey it sounds, I think it’s this level of deep connection with the creative spirit that turns artists into conduits — conduits for the human experience, of whatever it is that flows through us and the world to make things work (I’m not going to try naming it here), of the collective memories, wounds, hopes and wishes we share.

Perhaps one reason Mr. Prestage delivers such a punch is that, as his website explains, “Ben Prestage’s musical background began before he was born … even before his parents were born. Ben’s great-grandmother was a Vaudeville musican who toured with Al Jolson and in medicine shows. Her daughter was a Boogie-Woogie pianist and painter who used to play for Ben when he was coming up.”

Here’s an interesting mini-documentary about Ben:

The other aspect of Ben Prestage that gets me going is the fact that, like me, he’s a Florida native.  In fact, he’s from near where I grew up.  Unlike much of Florida goings-on I come across in this and other towns, Ben lets fly with the “country” side of Florida that I know and love, but often feel gets kicked under the rug in place of more “refined” or more “tourist-friendly” ways of being.  Something about Ben’s performance, unabashedly rough and down-home, validated and helped me revel even more in my roots.

Speaking of another side of Florida, I highly recommend taking a trip down to Stragglers. There’s live music every Sunday, and you can also pick up some delicious fresh-made Mexican-style pork or chicken tacos for just $2 each right outside. The owner, Will, was super welcoming and gracious with me when I asked about the place. “It’s just a good little neighborhood bar where people come to have a good time,” he told me.

Ben: Six shots strong by end of set.

I checked in with another couple of friends who came out — videographer da Lee Woodman said of Ben, “He was the best musician I’ve ever heard live.” Bootsy, who takes in tons of live shows at Pastimes Pub in Gulf Gate, shared: “It rocked my socks off. I lost one sock and can’t find the other.”

Ben plays the cigar box guitar.

Drum/cigarette holder.

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