I never liked the first book. The gunslinger killing a woman by shooting a gun up her vagina was just too much for me. As a result, I could never entirely see Book!Roland as a good person--just better than his opponents. (RPG!Roland is a different story altogether.) I got interested in Roland's companions in the later books, and I enjoyed the interstitial book Musesfool mentioned, but--the memory of that one action kept getting in my way.

Also, women suffer a great deal in this series, and often in ways that are hard to deal with. So...be forewarned.