PAIR OF PIRATES: THREE BUCCANEERS, ONE DELIGHTFULLY CROOKED JOKE

by Alan Linq

The first laugh often comes before the first note: Pair of Pirates walks out three strong. The math is wrong, of course, and that’s the point. It’s a running gag that has carried this crew—Elizabeth the Stowaway (Dana Smith), Jack the Rum Runner (Fred Flores), and Harvey the Corpsman (Dave Ruffin)—through malls, libraries, and heritage groups across Texas. The trick is simple: play with the joke, lean into the music, and keep the crowd smiling.

The name stuck years ago when the group was in fact a pair with just Smith and Flores, but even after Ruffin joined, the punchline was too good to abandon— and, as they note, the stationary was already written anyway.

This ship initially set sail when Flores and Smith (a true pirate couple!) decorated their home for Halloween and went all-out on a “Pirates of the Caribbean” theme. It was also then that Flores first stepped into the swagger of Captain Jack Sparrow. What started there has turned into a steady schedule of shows where history, humor, and harmony all sail in formation.

Pair of Pirates isn’t one-size-fits-all entertainment. For preschoolers, it’s nearly wall-to-wall songs—jump, wiggle, dance, repeat—with just enough chatter to move things along. Older kids get more story: the language of ships, the lives of privateers, the clothes and cannons that defined the golden age of piracy. Seniors and history buffs can expect a deeper dive where songs accent the stories rather than the other way around. The trio reads the room, trims the sails, and steers each show to fit the audience.

Their best-known programs include “Sailing the Seven Seas,” which pairs geography with music, and a new American Revolution set that runs from the Boston Tea Party to Yorktown. “Captain Jack’s School for Young Pirates” may be the most raucous—complete with mock swordplay, tug-of-war, and an inevitable moment when Harvey makes off with the treasure. At Christmas, they turn familiar carols into salty singalongs, booked this year for the Galleria Mall with more holiday stops in the works.

Crowds have grown. A NorthPark Mall show drew roughly 340, and a recent library appearance topped 500. Libraries have become a natural harbor, mixing the joy of a concert with a gentle nudge toward reading. They’ve also played fairs, heritage groups, and civic events, often tailoring their shows to match the host organization’s themes.

Backstage, the do-it-yourself spirit runs deep. Flores built a 19-foot pirate ship float large enough for a landing party, and the trio set up a home studio where they’ve recorded two albums and even made videos. One fan favorite turns their dogs into shanty stars, lip-syncing to “Wellerman.” Between the ship, the costumes, the sound gear, and the music itself, they’ve built a floating world that’s both playful and surprisingly professional.

Each member brings depth. Ruffin, 74, draws on decades as a teacher, principal, and actor. His theatre and history background gives weight to the stories, while his improv instincts keep every show fresh. Smith, 60, has been a flutist since childhood and once served as a drum major; her melodies give the group its lift, and her background in scouting makes her especially attuned to young audiences. Flores, 67, once hampered by stage fright, is now the arranger, guitarist, and builder, shaping both the sound and the spectacle.

Their priorities reflect both experience and age. Rather than grinding through multi-week Renaissance faire circuits, they prefer shorter stints—library tours, mall events, single-weekend fairs—where they can give their best without the strain of travel and heat. As they put it, a half-hour library show can pay about as much as a full weekend outdoors, and it comes with air conditioning. More importantly, it comes with the kind of laughter and engagement that feels like treasure.

For audiences, the result is pure fun. For the performers, it’s also a philosophy. Don’t sit still in retirement, they advise. Stay involved, volunteer, find ways to connect with young people. Time spent with kids and causes keeps the heart young. For Pair of Pirates, that’s the true secret to longevity—and the best reason to keep booking shows. The math may not add up, but the joy certainly does.

And that joy is certainly the X that marks the spot.