The numbers 2-4 at Apple come up quite often, but “how annoying it is to work with Tim Cook” isn’t a recurring thread, despite his also being one of the most famous, wealthy, and powerful people on Earth as well.
Joel Spoksky’s meeting with Bill Gates about Excel is famous lore in our circles as well, although I doubt Spolsky was ever even top 10 at Microsoft.
Werner Vogels comes up fairly often, too.