The 1960s changed America. Comedy brought change to culture and our culture transformed comedy. As mirrors of what was happening in our society, stand-up comics and sitcoms began to explore life in novel ways. Situations started to become more realistic and, in some cases, edgier. TV sitcoms became less idyllic and more representative of “real life.” Issues not previously discussed openly in entertainment venues became the new norm. We will discuss the icons who showed us a new side of ourselves we hadn’t seen before, and the influences of rock and roll, Vietnam, drugs, and “the age of Aquarius” which brought unexpected changes that continue to affect us today.