The 1966 Game: Who’s Frank Sinatra Now?

This may be the most critical game piece yet.

Frank Sinatra was a fabulous entertainer and the rest you can argue about.

But he was also, politically, a very important figure in American history.

That’s because, during the course of the 1960s, he quietly switched sides.

Sinatra had sung Kennedy’s 1960 theme song, "High Hopes." But by the end of the decade it was clear that he, the old Rat Pack, and his entire generation had come to embrace the GOP.

This was literally the swing vote which put a generation of Republicans into office. Swing fans were disenfranchised during the 1960s by rock-and-roll. There had been swing hits in the 1950s, but by 1966 there were none. Those who tried to sing in any metier other than rock were ridiculed by just about anyone under 25.

Sinatra and other swing artists suffered from this. They did not enjoy watching their audiences age before their eyes. And they didn’t like rock music, not at all. It symbolized, for them, a lot of what was wrong with the world. It was loud, it was atonal, it was just guitars and drums and noise.

Sinatra made a few bows to the new boss. I think he was proud of his
daughter Nancy’s one hit, "These Boots are Made for Walking." But it
was clear, even by 1965, that his own hipster days, and his days as a
movie icon, were fading. So artistically he retreated into what he knew
and liked best. He embraced the stylings of Nelson Riddle. He did some
of his best work.

And, by 1970, everyone knew (without his having to tell them) that he
was a diehard Republican. Same with his fans. Same with his generation.

So who’s Frank Sinatra now?

Remember, we’re looking for a seminal artist (doesn’t have to be a
singer) who was wildly popular at the start of the decade, and
associated with Republican politics, but who now seems to be leaning
the other way, and who is likely to be widely seen, by their
generation, as a Democrat.