For Freestance I would think that the Cassin Ridge would have to be up there.
For myself.
One of my proudest would have to be the first time I did The Nose. I had absolutely no idea what I was getting into. We had perhaps a full set of cams ( some of them home made ) and a ton of stoppers , a 45 meter haul rope ( at one point I was pushing the haul bag up over my head so that my partner could get to the belay ), a home made haul bag that jammed up under every overlap and literally needed Duct tape to hold it together in order to get to the top.
The haul bag was black and had 1" straps, both for the haul points and for carrying. After a bit a took on a very sinister aura and became known as the haul bag from hell. It seems to have an evil grin. To carry this bag was to suffer. Hauling it was a nightmare. I have no memory of who carried it off the top. There is some kind of mental block in place guarding a very dark place. We were ill prepared.
Two days before heading up we went and climbed Waverly Wafer, Wheat Thin and Lady Fingers. That was the highest my partner had ever been before getting on El Cap. He also did not speak English very well. So during real stressful times we would just yell back and forth for a while then give up and do what ever seemed right.
It was blazing hot ( only one other party on El Cap ), I had read one to many stories of Warren Harding so I was absolutely convinced that 1 and 1/2 liters of water per person per day was all that was needed to do any wall. We packed one spare liter for each person.
It took us five days. We hauled the first four pitches since we did not know about the Sickle raps. We were so slow that every day for the first three days the rescue helicopter would fly by us and see if we were still alive. On the third day I flipped them off, my partner waved for a rescue. We yelled, cursed and proceeded on. We climbed from before light to well after dark every day.
We got incredibly dehydrated, at one point I almost choked to death on a bit of canned tuna. Power bars were popular back then. We had a whole bag of them when we started the route and for the most part had a full bag when we finished. It is nearly impossible to eat a power bar when dehydrated and lacking water.
When we got down we rushed to get to the Deli. The doors were locked and a couple folks were cleaning up. We must have had quite a forlorn look cuz they opened up and let us have the run of the place. I think I had six dollars. I was on top of the world. In the check out line the gal behind the counter asked if we had just done El Cap. I proudly stated yes. She very non-chalantly said, "oh, so you are the guys that were on The Nose?... "You guys were slow".
It was one of my proudest moments and yet one of my most humbling. W