wow, thats a tough question, I really liked 5, and 6 and 7, but then again they were all awesome and i literally didn't want to do anything else when i was reading them, i think that after I'm done reading everything's eventual im going to read them all again, can't wait!
My favourite is book four. Five and Six. Number six because SK was a character in the book. I was so excited about this when first starting reading it. That has definately been a real highlight for me. I do hope he is in book Seven!!!
I'm in the love for 'em all camp. They all are different, but good. I guess my softest spot would be for The Gunslinger, just because it was my introduction to Roland and Jake and the whole world. The original though. I didn't read the revised until later on when it was published, and I like it too, but the original is the one I always remember. Next would probably be Waste Lands, it catches my mind with curiosity in so many ways about the locales they see, what happened there, what'd those places used to be like back in the days of old? But I love Drawing of the Three for the introductions to Eddie and Sus', and getting to know Roland better, and seeing his reactions to their when and where. Wizard and Glass for the story of Roland's youth and getting to meet his old friends, and Wolves of the Calla for the deeper insight into the worlds, and seeing Callahan again and hearing his story. Can't comment just yet on why I love Song of Susannah and The Dark Tower, because I'm currently working on a series re-read myself and haven't gotten to those two yet. But I can say that I really,really loved Wind Through the Keyhole, loved the story-telling style of it, and the fairy-tale feel of the title story about a boy named Tim.
So... yea, love 'em all
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