Heh, one of my personal "best" movies is Plan 9 from Outer Space... With that, here's my trick to find books/movies/music in more specific (or somewhat peculiar) genres: look for reviews or go shopping for the ones you already like/have.<p>IMDB has related movies/suggestions as well as Amazon (read the comments also, there might be more mentioned.)... sometimes you find other gems along the same line you were thinking.<p>Look at the production company, director, author and see whatever else they are attributed to.<p>One place I can recommend to finding a good movie blind is looking through the "Criterion Collection" videos and DVDs (Hulu has many of em, but not all), which is like the ultra-fan special edition of classic films, most of those are notable for some reason or other.<p>Lastly there have been several threads here on great books movies, do some searching and you will find em.<p>For music (besides amazon) - if you like particular genres check out some streaming radio stations - i.e. for the jazz fan Play Misty For Me radio or Luxuria... There's a streaming station for just about any interest. Shoutcast is a good place to start hunting for streaming stations.
My "hack" is to ask strangers the following questions:<p>"I'm going to watch a movie tonight, what's a really good movie that I probably haven't seen."<p>This works best with strangers or people you've just met. I find that people who know me always recommend movies that I've either already seen, or decided that I don't want to see. If the stranger has any affinity towards movies, they can almost certainly come up with a gem that you've never heard of.<p>I discovered this works when I asked this exact question of someone on a whim and they recommended "Castaway on the Moon". It was a darn good movie, that I never would have found/watched on my own. I've since asked this question of all sorts of people with great results.
Before the Kindle came out I would read the covers of books of people sitting opposite me on the Tube. If it looked interesting I got a copy. The only major fail I remember was Dan Browns The Davinci Code.