For Christmas, I received iTunes gift cards. I thought it’d be nice to get some movies for my iPod Touch, but once I get into the store, I find myself paralyzed with indecision, compounded by the fact that the missus and I don’t get out to the movies much. 
So I need some recommendations. I like fifties sci-fi, the Thin Man series, Sherlock Holmes, and Westerns. I liked Watchmen, but not The Dark Knight. I like Hitchcock, but dislike slashers. I liked From Beyond, but not Bride of Re-Animator. I like naked women, but am uncomfortable with explicit sex, and kissing scenes bore me. I loved Juno, but disliked that one with the blonde gal from the hospital show who ends up pregnant and decides to marry the schlub (although I wouldn’t mind seeing more of Leslie whatzerface, the bitchy wife of Paul Rudd). I liked The Fifth Element, and disliked the Star Wars prequels.
I can afford to buy three movies. They’ll have to be fairly modern (iTunes is weak on old movies), not too mainstream (I have a big DVD collection that includes most of the classics), and rewatchable.
Let me have your recommendations!
Three modern westerns that I really like: 3:10 to Yuma, The Assassination of Jesse James by the Coward Robert Ford, and No Country for Old Men.
If you want a sci-fi movie, a couple of my favorites are District 9 and Sky Captain and the World of Tomorrow.
Some other modern favorites of mine that you might like: L.A. Confidential, Memento, Sin City, Inglorious Basterds, Stranger Than Fiction, Gran Torino, and The Prestige. I’m not sure how high the last three are on the rewatchability scale though.
Or you could get the Lord of the Rings trilogy.
JMO: Why don’t you list ten or so movies you’re contemplating purchasing and get reactions on those titles?
Were I in this situation I would go to Netflix, find something I like, open that page, click on genera and get a list of similar films, use that as a list of recommendations that may be available on the other device.
One could do something similar with GreenCine. Does iMDB have genera lists?
Just going by your summation of likes and dislikes, you might enjoy Observe and Report. A strange, quirky, and slightly dark and cynical little comedy. I could have swore that it was written by Patton Oswalt, but turns out he just acts in a minor role.
IMDb has a “if you liked this movie, you might also like…” section at the bottom of each movie page.
Personally, I’d get music. I can’t imagine watching a movie on that tiny screen!..TRM