“You want a beer, you get your own beer.”
Like any good squall, Captain Ron comes on you fast, and it leaves you fast.
I first came across this movie sometime in the ’90s, probably around the time it came out, but I devoured it in the early 2000s during late-night screenings aboard my family’s fishing boat.
Docked in South Florida, my we had the practice of spending the night aboard before offshore fishing days. Tucked into the small cabin, stretched out on the vee-berth with beer cans and popcorn splayed out on the small table, we watched a small stable of movies on repeat. A lot of John Wayne films, The Quiet Man, McClintock, In Harm’s Way. Erroll Flynn’s Captain Blood and Robin Hood. Tyrone Power in The Black Swan. Tombstone.
Captain Ron was an outlier, a goofy modern-day comedy amidst a series of westerns and adventure stories set deep in the past. But Captain Ron speaks to me.
Let’s get one thing out of the way. Captain Ron was panned critically. According to the professionals, the movie wastes Martin Short’s comedic talents and misuses the machismo of Kurt Russell. They didn’t like the jokes and thought the storyline hokey. But they missed the fucking point.
Captain Ron is an escapist’s escape. Sailors and pleasure cruisers today still love the movie for capturing so well the culture of travel in the Caribbean.
The movie centers on the Harvey family, a suburban Chicago clan who find themselves the sudden owners of a 60-foot sailboat courtesy of a deceased uncle. They had no plans to ever set foot on the boat — intending to sell it and pay off the mortgage — but their minds change when their 16 year-old daughter arrives with a wedding ring on her hand, courtesy of a pierced metalhead. They decide on the spot to take a month off and sail the boat from its current moorings in the Caribbean to Miami where they still plan to sell the boat.
The first glimpse you have of that Caribbean is the family’s arrival on San Pomme de Terre (“Saint Potato), a backwater of an island with chickens pecking and broken down buses surrounded by the beautiful Caribbean Sea. They’ve just left their suburban Chicago life for the adventure of a lifetime. They’re not impressed.
Things get worse with the arrival of the movie’s namesake, a one-eyed drunken sailor with no sense of direction or propriety. Captain Ron exudes saltiness but not competence, and he takes the family through misadventures and mishaps over the movie’s course, unwittingly tormenting Martin Harvey (Short) while bumbling from no-name island to no-name island. There are guerillas, pirates and tattoo artists. The character development comes on the side of the Harvey family, who grow from pale landlubbers to adventurers over the course of the film, and the chief conflict, as mentioned, is between Harvey and Captain Ron. It’s a beautiful setting for the silliest of stories, and it’s one of the most underrated comedies of the ’90s.
The Harvey family are modern pioneers minus the ambition. They have everything they could ever need but find life improved with fewer strings and worldly possessions. And if the Harvey family are new pioneers, Captain Ron himself, wandering, adventurous and unmoored from any personal drive, is the logical descendant of Captain Henry Morgan, restless buccaneer cum royal official.
Outside a weekend in Nassau that nearly got me deported, I’ve spent little time in the actual Caribbean, but I have spent a great deal of time in South Florida, a land of boozers, adventurers, misadventurers, con artists and heiresses. Much of my late teens and early twenties were spent sneaking off to the Square Grouper in Jupiter for late night beers, and I’ve hung around the marina docks enough to know that the characters in Captain Ron are real enough, a late-’70s Jimmy Buffett song come to life. Nearly everyone living in those particular latitudes are there because they have no place farther north. They’re unable to survive with the rest of us, so they bug out. But not everyone who dreams of doing so can actually make the move. Some of us have different ambitions, different responsibilities, and different dreams.
And that’s the magic of Captain Ron. For anyone who has ever had a mishap on the high seas, found themselves down and out in a foreign country, or vomited in an engine room, the movie will feel familiar. And for those whose days are primarily spent staring at computers, the movie offers an unfailingly pleasant vision of what hijinks await … if you only bought that boat.

