Cayman Went plays out very similarly to the main character’s television career. It has a promising beginning but ultimately tanks and never recovers. The film’s mix of Lifetime drama and heartwarming family comedy places the film in genre limbo: the film is too serious to be a family comedy yet too innocent and innocuous to be an over-the-top Lifetime movie to boot.
Josh Anders (Mike Lombardi) has a career that hasn’t quite amounted to what he wants it to be. Initially diving into an ocean of fame via his hit TV show Diver Down, Josh’s fame was brief, and now he’s relegated to doing mall autograph signings and other more pedestrian public appearances. However, his life takes a turn for the better when real estate mogul Martin Perkins offers him a chance to restart his TV show if he goes to the tiny island of Cayman Brac to settle a deal so Perkins can build a luxury resort. It seems that Josh is still popular there, as the island is “that” remote. Josh’s intentions are clearly altered once he arrives on the small island, as he learns more about himself while getting to know the island’s inhabitants to boot.
Director Bobby Sheehan crafts what seems, at first, to be a low-budget indie flick about finding yourself and overcoming those tried and true obstacles of life, but the main premise soon becomes a bit ridiculous once Josh lands on the island. While the island is small, it’s hard to buy that a place in an area that’s a prime vacation spot would be cut off from society to the point of the residents being stuck in a pop culture time warp. If you can get past this, Cayman Went offers a mildly pleasing, if definitely generic tale of self-discovery that also makes the film somewhat difficult to define. While the film is family-friendly and the story is certainly not complex, it may be a bit too serious for a family trip to the movies. You may relate to the idea of “finding yourself,” but it’s pretty much guaranteed that your five-year-old isn’t going to feel the same way.
Sheehan eventually chooses to take the family film route and wraps Cayman Went up nicely — you can probably already guess what happens. In his director’s statement, he cites many influences in his style of filmmaking, such as Days of Heaven and The Bridges of Madison County, though I assure you that you aren’t going to find anything like that here. As far as I could tell, I saw no jaw-dropping cinematography nor doomed love story to speak of, and I know that I was definitely searching hard enough. Cayman Went doesn’t quite amount to the efforts of Eastwood or Malick, but honestly it shouldn’t have to. It is what it is. While it fails as a contemplative indie film or a serious drama, you could do a lot worse in terms of family films (live-action Garfield, I’m looking at you) and in that area, Cayman Went isn’t actually half bad.