Article Contributed by Russell Levine
Published on 2026-06-22
BERTHA: Grateful Drag | Key West, Flordia | June 5th, 2026 - photos by Russell Levine
Five inches of rain in four hours will get your attention.
By late afternoon on June 5, parts of Key West looked less like a tropical paradise and more like an aquatic obstacle course. Streets flooded. Tourists scrambled for cover. Locals shrugged the way locals do when the sky decides to dump an inland sea on their island. And somehow, in the middle of all that, BERTHA: Grateful Drag was preparing to open Pride Month at Key West Theater.
A flooded island. Pride Month. A theater full of Deadheads. A Grateful Dead drag band finally arriving in Key West. Sometimes the story practically writes itself.
The rain finally stopped just before showtime, and as people emerged from bars, restaurants, hotels, and wherever else they had sought refuge from the storm, they began making their way toward the theater. By the time the lights went down, the room was nearly full. The Key West Theater's dinner-show layout leaves limited room for dancing, but that proved to be little more than a suggestion. Nearly every table was occupied, the upstairs balcony was packed, and before long the aisles had become makeshift dance floors.
The atmosphere was pure Key West. People were drinking. People were laughing. People were dancing. People were very clearly in vacation mode.
The spirit of the evening revealed itself before a single note was played. Standing in the lobby, I spotted what appeared to be an entirely normal Deadhead. Comfortable shirt. Casual shorts. Standard-issue Grateful Dead attire. Then he turned around. Stiletto heels.
Nobody blinked. Nobody stared. Nobody cared. It was Key West. It was Pride Month. It was a room full of Deadheads. The jury had already reached a verdict: be whoever the hell you want to be.
That philosophy seemed to run through the entire evening.
Throughout the show, members of BERTHA spoke about how excited they were to finally bring the project to Key West. For a group built around celebrating individuality, community, and self-expression, there may not be a more fitting destination. The performers clearly understood that. The audience did too.
What surprised me most was how many people had already become devoted followers of the band. Roughly a quarter of the audience members I spoke with had seen BERTHA multiple times. Several described mini-runs built around the band's performances. They had traveled to Key West specifically for this show and were thrilled the group had finally made it to the island.
The first-timers were there for a simpler reason. They wanted to hear Grateful Dead music. And once the opening notes of “Shakedown Street” rang through the theater, they got exactly that.
Any lingering questions about whether BERTHA was a gimmick disappeared almost immediately. Within minutes it became obvious this wasn't a novelty act built around a clever concept. This was a band filled with serious musicians who understood both the technical and emotional language of Grateful Dead music. The groove settled in. Heads started bobbing. People rose from their seats. The party was officially underway.
Every member of the band had their own moment throughout the evening.
Jacob Groopman energized the crowd by drifting through the audience while playing, erasing the invisible barrier between stage and crowd that has always been part of the Grateful Dead experience. Justin Showah added rhythm, personality, and one of the evening's most entertaining surprises when he appeared with a washboard during the percussion segment.
Thomas Bryan Eaton repeatedly reminded everyone that he is a serious guitar player with genuine talent. His leads were confident, tasteful, and powerful. The man can flat-out play, delivering some of the night's most memorable riffs. Caitlin Doyle combined an outstanding voice with natural stage presence, commanding attention whenever she stepped to the microphone.
Mike Wheeler held everything together with strong playing and, occasionally, some surprisingly decent dance moves that drew more than a few smiles from the crowd. Alex McMurray moved effortlessly around the keyboard, adding color and texture while somehow always finding exactly the right notes at exactly the right moments.
And Melody Walker served as the band's center of gravity throughout the evening. Her voice, presence, and leadership seemed to hold the entire production together. As a photographer, I also have to mention her makeup, particularly the Grateful Dead lightning bolt framed in rainbow Pride colors around her eyes. It was one of those visual details that perfectly captured what BERTHA is all about.
The band's warmth extended well beyond the stage. Jacob and the entire BERTHA organization were incredibly welcoming, providing full access for photography and spending time discussing the project backstage. The positive energy they projected from the stage proved equally genuine behind the scenes.
One of the evening's most enjoyable interludes came courtesy of local drag queen Beatrix Dixie, who introduced the band and later returned during the set break for a spirited mini-performance featuring singing, dancing, and plenty of audience interaction. The crowd loved it. Beatrix also pointed attendees toward the official after-party at a local nightclub, ensuring the festivities would continue long after the final encore.
Musically, several moments stood above an already impressive performance.
“Bird Song” was a technical masterpiece, exquisitely played from beginning to end. Every musician contributed, creating one of the evening's most captivating performances.
Later, the transition from “Truckin’” into “Eyes of the World” transported me back to the intimate Grateful Dead theater shows of the late 1970s and early 1980s. For a few minutes, time seemed to collapse. The connection felt immediate and familiar, the way great Grateful Dead music always does.
But my favorite moment arrived early in the second set. Most Deadheads know the opening lyric of “Scarlet Begonias” by heart: “There's a dragon with matches that's loose on the town...” BERTHA had other ideas.
“There's a drag queen with matches loose on the town.”
The room exploded. It was funny. It was ridiculous. It was perfect.
In one lyric, BERTHA explained the entire evening better than any reviewer ever could. The line captured everything happening inside Key West Theater that night: Pride Month, individuality, humor, acceptance, and a deep affection for Grateful Dead music. It wasn't parody. It wasn't mockery. It was celebration.
As the show approached its conclusion, the band delivered one final gift with “Uncle John's Band.” Few songs better embody the communal spirit that has kept the Grateful Dead experience alive for generations, and it proved to be the perfect choice to close the evening.
As the final notes faded away, the audience spilled out onto Duval Street and into the wonderfully chaotic energy of Key West during Pride Month. Pride flags waved in the warm night air. Music poured from open doorways. The after-party was just beginning. Somewhere nearby, somebody was making a terrible decision that would become a great story tomorrow morning.
Which, now that I think about it, is exactly how a Grateful Dead evening is supposed to end.
For this longtime Deadhead, the biggest takeaway was simple. BERTHA may attract attention because of its concept. But that's not why people come back. They come back because the music is real. The musicians are real. The community is real. And on a flooded June evening at the southernmost point of the continental United States, that was more than enough.
Russell Levine is a photographer and writer covering live music for Grateful Web. He has been documenting the jam band world and its community for years, camera in hand and a few decades of Dead shows in his bones.
