I began wit Aristotle (because you know, he was the first). I never finished his Organon since it was terribly, terribly boring. I never read anything else, so I ended with Aristotle.
Maybe try listening to http://www.historyofphilosophy.net/ . It is very good. Almost as good as, say, a giraffe.
Also, for easier reading in general, people that wrote in pretty much the language you are reading are good for working up some philosophical inertia before plowing into tougher soil. I always recommend Hume. Rereading something like his epic philosophical burn on the design argument is just fun but then, that's me.
But it's really terribly long (since he had the idea that he has to describe EVERYTHING) and, at times, it doesn't make sense from today's perspective of today's logic and set theory.