I would say I've seen each of the original trilogy a couple of hundred times. We got the tapes when they were first released on video. I watched at least a part of them each day for a long time as a child. I didn't watch them as much around junior high and high school. After a while, the tape broke. The only version available at the store was the Special Editions, so I bought those. I hated the Special Editions, so I basically stopped watching them. Thankfully, through the internet, I was able to buy the originals. I limit myself to watching them once a month.
So I would have to approximate-New Hope-300 times/Empire Strikes Back-250/Return of the Jedi-200
For Phantom Menace, I saw it twice in theaters and have the DVD. I watch it every few months. Probably seen it 15-20 times.
I've seen Attack of the Clones twice-once in the theater and rented it once on video. That is all I could stand of it.
I've made a pledge to never again pay money for anything George Lucas puts out until he puts the original movies, not the Special Editions crap, on DVD. I will see Revenge of the Sith in theaters, but I'm going to wait a few weeks until the theater allows me to use a free pass.