This is a great thread, and one that has come back to life after nearly two years of death. When I first started climbing in the Gunks, there were the BIG 3 5.6's to do...Shockley's, Madame G's, and High E. The only one worth 3 stars is Madame G's. That being said, the middle pitch of Shockley's is probably the best pitch of 5.3 climbing in the Gunks. Just forget about the last pitch and do the route at 5.3...you'll have a much better experience.
I tend to not like contrived, squeezed in lines. Someone mentioned Turdland, and I think that falls into the contrived category nicely. I will put up my personal vote for worst starred route. It may not get 3 stars in the book, but Overhanging Layback doesn't deserve any stars as far as I am concerned. The crux on this thing is completyely contrived. It's 5.7 only if you do everything in your power to avoid the footrail 6 inches lower that makes it about 5.4. Shitty climbing.
I'm gonna get beat up by my next offering. Never Never Land has always struck me as quite possibly the very worst of Gunks climbing all packed into one pitch. Off angled climbing on greasy, sheared off glass crystals, protcted by bolts. I've been on this thing once and would NEVER voluntarily do it again.
Someone put Simple Suff in this list?? I have to protest. That is a fabulous route, once you get away from the ankle breaker start.