Some speech issues that come to mind which, I sometimes wonder, how they would have gone down today:

* The 6.001 porn

* The ghetto party

* The Reg Day porn (particularly Deep Throat, but many)

* The Visualizing Cultures display (with CSSA opposition)

* Some 10% of the day to day traffic on senior-house@, bexley-minus-fascists@, and ec-discuss@

Norms around speech have evolved a lot even as the fundamentals of ethics and laws on the electronic frontier have stayed the same. I often think that folks in the 80s and 90s enjoyed, for better or worse, considerable latitude in their speech which wouldn't fly today.