You have to first understand that the Reagan years were the culmination of a tumultuous time in our history...by the end of the 1970s, after Vietnam, Watergate, economic stagnation and the Iran hostage crisis, the USA seemed to be turning on itself and many around the world wondered if it's time as a Superpower was finally coming to an end.
By the end of Reagan's second term, not only had the nation's Superpower status been affirmed, we found ourselves the world's sole Superpower as the USSR crumbled. For generations raised to constantly fear the possibility of nuclear annihilation, there finally came an opportunity to heave a giant sigh of relief.
With the end of those tensions, there was great elation (which led to Bush 1.0's first victory) but as with the end of any long stretch of adversity, there was also a great deal of fatigue.
A large generation of younger Americans (myself included), raised by parents who survived the Depression and WW2, were tired of hearing the same old rhetoric about how we had to be "good Americans" and live a certain way.
Up to that time, Presidents and Presidential candidates were like the father figures from old 1960s TV shows...They talked about "old values" and listened to Big Band music. They had gone to war and played football in college...
Along came Bill Clinton who spoke the language of the 1960s and played the saxophone. He yucked it up on MTV and quoted Maya Angelou with late-night talk show hosts. Like so many of us coming of age, his was a mentality that was formed in the 60s and 70s, rather than the 40s and 50s.
Ironically, it was Bush's "nice" side that cost him most. He was a hardened old Cold Warrior who was greatly respected among world leaders of his generation...but to younger Americans who never knew black-&-white TV, he appeared a tired, mild and uninspiring old man.
Bush promised to maintain the course that won the Cold War...Clinton promised to look ahead to a new era, free from that "old" sense of obligation and guilt.
For the nation, it was like a teen being given a choice between spending a weekend with a kind but stern uncle, or a cousin who roadied for a rock band and smoked weed with celebrity friends.