As for 'Monkeys', I agree completely that it IS a great film with one of the better red herrings in the history of cinema. As much as I like Bridges, it would not have been nearly as good without Willis. Willis basically plays a somewhat cartoonish thug akin to 'Marv' from Sin City (that's not a jab at him at all), and I don't think I could ever believe 'the Dude' to be the somewhat dimwitted lout that Willis portrays (again, that is NOT a jab at Bruce). He's brilliant in this movie and he has to be applauded I think, for working with directors that were not exactly in the mainstream. Gilliam's work has not really appealed to the masses (which is a shame, really) at least when they're not released. This is one of his films that feel much more restricted because of 'studio expectations'. It's not a typical mainstream film, but it
You also mentioned Pitt possibly being the biggest draw of the film at the time, but I disagree, at least here in America. If I remember correctly, Pitt was still being regarded as a 'pretty boy' by most male moviegoers even if he had already been in several movies that contradicted that image (like Kalifornia, for one). I also remember a number of his rabid fans (mostly female) being extremely taken aback by Pitt's 'Twelve Monkeys' performance consisting of many tics and facial contortions. It greatly amused those of a certain age.
I liked Looper, also, but I think it's far more flawed than 12 Monkeys (and there's no Frank Gorshin... Things were always better with Frank).
And one comment on the choice for the Film Club. I get that you came up with the choice of Twelve Monkeys by someone mentioning Looper to you, but I think a better choice would have been a Gilliam movie that few people have seen, like Tideland, for instance. I also would have liked to hear what you thought about (I couldn't find anything on youtube other than you asking Gilliam about it, sans an opinion).