Before watching the movie:
Full disclosure: I went and found this movie because it was mentioned on an episode My Brother, My Brother, and Me. I don’t recall what question led one of the brothers to bring up “when Martin Short inherited a boat and knew nothing about sailing in Captain Ron, he went out and found Kurt Russell”, but all I needed to hear to be interested was “Martin Short inherited a boat knowing nothing about sailing”.
I wasn’t entirely prepared for the personality clash set up here, but it’s not terribly surprising. Martin is a straight-laced man dumbfounded by Ron’s party animal ways. That’s a pretty standard setup, and those are types they slot into well.
After watching the movie:
When Martin Harvey inherits his uncle’s yacht, he wants to take his family down to the Caribbean island it’s moored at to personally sail it to the yacht broker in Miami. His son Ben is excited about the boat, but his wife Katherine is reluctant to uproot the family for weeks with little notice until their daughter Caroline announces that she just got engaged to her seedy boyfriend. When the Harveys find the yacht in much more serious disrepair than expected, the yacht broker decides that rather than sending their best skipper to guide them, they’ll just get some local sailor, who turns out to be Captain Ron. Ron’s lackadaisical attitude toward everything gets under Martin’s skin. The family all loves Captain Ron, but Martin is convinced he’s going to get them killed or kidnapped.
I feel like the 90s was particularly in love with the “serious and neurotic patriarch driven batty by his family’s preference for the fun, harmless rulebreaker” plot. The father feels replaced by the cooler newcomer and tries to undermine him, so it’s kind of a cuckholding sort of story, but almost always as family entertainment. I was actually surprised by Ron’s precision use of the PG-13 limited profanity allowance. Maybe the degree to which Martin and Katherine get frisky with each other would have pushed it for PG, but I never thought it wouldn’t have been until that line.
This isn’t one of Short’s more comical roles. He’s almost playing straight man. That doesn’t mean he’s not funny, but he’s funny in a very grounded, reactive way. Ron is the outlandish one, but the humor comes from Martin calling out how weird it is. It’s a dynamic I haven’t considered much.
This is just a fun little story. I wouldn’t expect an obscure pop culture reference from the McElroys to be great cinema, but this isn’t even a popcorn film exactly. Some familiar and funny actors get set against each other and funny things happen for a while. It’s not a very memorable or noteworthy experience, just fun.