The premise of Churchill: The Hollywood Years (that Winston Churchill was actually an American marine, rather than a British statesman) is quite an astute piece of satire on the Americanisation of history (U-571, anyone?). It does, however, fall down in one key respect: there is nowhere near enough material to fill a film, even one as short as this.
While there are some amusing moments (none readily come to mind, but there was some laughter), it does get to be a bit cringeworthy. This is not just because of the ridiculous ideas, but the truly awful acting on display by everyone; there’s slapstick and bizarre, and there’s just plain shite. This falls in the latter category far too often.
It’s not dramatic, it’s not character-driven, and it’s not funny enough to have warranted more than a recurring character in a sketch-show. Had the writer gone down that route, we’d have a fairly well-liked character. As it is, Churchill is a bit too drawn out to be entertaining.