This movie tries hard to be like Eternal Sunshine of the Spotless Mind, but it doesn't succeed. The main problem is that the characters are very underdeveloped and don't really have personalities except for "freak-ish rebel-ish cute girl", "stuffy, obsessive, boring-but-not-really guy" etc. (the other characters have even less of a personality).
It's apparent in the performances too that the actors didn't have that much to work with. The actors aren't really investing much, it's pretty light and superficial stuff - which would be good if this was a straight comedy, but it isn't. The movie really wants to say something meaningful (it screams "MEANINGFUL" from the very first scene - a shot of the earth, then zooming closer and closer and into the protagonist's bedroom), and it also wants to be sad and for you to root for the main guy and all those things. You know, it wants to be realistic, it wants you to suspend disbelief. It halfway succeeds at that, because it's very competently made and briskly edited, and filled with jokes and funny situations, half of which semi-work or more. (The other half have already been done better in an average Seinfeld-episode.) The other problem (except for the flat characters and the fact that it isn't nearly as funny as it tries to be), is, as others have mentioned, the cringe-worthy plot contrivances. The clichéd and cringe-worthy scenes have to do with the same thing as the problematic characters, weak and unimaginative writing. What you think will happen between the two leads, happens, and in the most well-used way.
Lastly there's the absurd plot developments. The whole premise is absurd of course, like it was in Eternal Sunshine too. But the characters in Eternal Sunshine reacted to the absurd situations in a way consistent with their personalities and the world they occupied. The world in Stranger Than Fiction is neither-nor. Mostly it's clear that the movie attempts to convey a certain realism. I could give lots of examples of this but won't bore or spoil you. But then a character like Professor Jules Hilbert (Hoffman) suddenly accepts Harold Crick's (Ferrell) explanation without asking HOW or WHY this would happen, the same does Crick himself and two other characters. Suddenly we've entered fairytale-land. That Crick so readily accepts his final outcome (and the reason he does so) is also hard to buy, and not consistent at all with his character as presented. So the movie ends up being neither this nor that.
"Luckily" most of these revelations and plot developments don't happen before later in the movie, and we can't be sure where the whole thing is gonna go (metaphysically) before that. By then I'd already started to somewhat enjoy and be entertained by the movie (when I wasn't annoyed or cringing).
The actors are OK but nothing more, as I said they don't really convey a lot of emotional truth - Maggie Gyllenhaal being the possible exception. Emma Thompson is mugging too much, Dustin Hoffman plays Dustin Hoffman (nothing wrong with that), and... there's nothing to say about Queen Latifah or Will Ferrell.
In summation, a slight, but entertaining movie that tries to make you think it's very profound.
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