As for 1969, it was generally the same sort of year of extremes of good and bad that 1968 was, with brutal senseless murders instead of political assassinations being the main distinction.  Also the beginning of a pull-back or reaction by the corp media against 60s counterculture, with the Smothers Bros tv show being cancelled (pressure from Nixon admin).  Though at the end of the year, Dick Cavett's late night show was launched which would eventually incorporate some 60s political/cultural sensibility in his quirky and often interesting guest list.

Beatles essentially broke up that year and Paul was reported to be dead, as cleverly indicated at the very end of Lennon's song I Am the Walrus (iirc) when played backwards ("I buried Paul").  F. Lee Bailey came forth helpfully and hosted a nationally syndicated teevee show to explore further into this mystery.  

Woodstock was outstanding, but seemed to announce the end of an era.  Some knuckleheads out here -- Jerry Garcia and the Dead or the Rolling Stones, I forget -- thought it would be a neat idea, as they tried a west coast version of Woodstock, to hire the local Hell's Angels chapter as security, then to pay them not in $ but in cases of beer.  With predictable results.