Having inherited a yacht which once belonged to Clark Gable, Martin Harvey (Martin Short) 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). 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.
9 times out of 10 when I come across an older movie, but one made during my lifetime, which features some familiar actors yet I have never heard of it, I can be pretty sure it is going to only be average at best. So when I came 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 movie has only 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" may have some sort of nostalgic charm but for me it comes up short.