Having inherited a yacht which once belonged to Clark Gable, Martin Harvey (Martin Short - Three Fugitives) convinces his family that they should all leave Chicago and head to where it is docked so that they can sail it back as a family before selling it as it could be worth something if they get it back to the mainland in one piece. But having never really sailed before Martin hires himself someone who can, the eye patching wearing Captain Ron (Kurt Russell - The Best of Times). Despite being polar opposites Martin learns a lot from Ron and not just about sailing and not always intentionally as Ron's laid back attitude and flirting with his wife forces Martin to take control of the situation rather than be pushed around.
I have a rule of thumb: if I find a movie I have never heard of yet it features famous actors and was made during my lifetime then it is likely to be average at best and mostly below average. So when I stumbled across "Captain Ron" with a cast featuring Kurt Russell, Martin Short and Mary Kay Place I just knew that something had to be wrong with it as I had never heard of it. And I was right because for a comedy there is little which is funny about "Captain Ron" and the storyline which is really about Martin taking control is so familiar it is sadly tedious.
In fact despite "Captain Ron" starring Martin Short this is a movie which relies on one joke and that is Kurt Russell as the eye patch wearing Captain Ron who is a total dog around women including Martin's wife as he walks around the boat in budgie smugglers. Oh there are other jokes in the movie, there is one where Martin ends up overboard having fallen victim of a belt sander but any joke which comes close to working generally revolves around Kurt Russell playing it laid back and dirty as the titular Captain Ron.
What this all boils down to is "Captain Ron" just doesn't work and is not only typical in that we have a city guy who is a pushover taking control but we also have little in the way of comedy other than Kurt Russell playing it rough and ready. Maybe for those who were children back in 1992 "Captain Ron" might have some sort of nostalgic charm but for me it comes up short.