Was there ever a time in recent history where right-wing politics were "cool"?

[Schiff for Senate]

Here's who I think was perceived as "cool" and "uncool" in American politics since the 1960s:

1960s: When it was coolest to be left-wing. Young student activists and visionary idealists associated with the New Left defined political coolness in this period, while equally cool figures like Timothy Leary and Allen Ginsberg served as elder (over 30) statesmen for the political and social counterculture. That's not to say hippies were necessarily cool, but the college kids who protested the Vietnam War, smoked pot, listened to Jimi Hendrix, and spearheaded the Sexual Revolution definitely were.

1970s: Richard Nixon might be the most remarkably uncool person in American history, so anyone opposed to his administration was by comparison at least decently cool. After Watergate, when Americans lost faith in their government, it was cool to just not give a damn about politics anymore and spend all night at the disco high on Quaaludes.

1980s: When it was coolest to be right-wing. Ronnie Reagan brought the nation back from the brink and made us proud to be American again, feared abroad and respected at home. In the 80s, there was nothing cooler than the Red Dawn kids kicking some Commie and Russkie ass, while aspiring yuppies looked to Gordon Gekko's "Greed is good" Wall St. life as a source of inspiration. At the same time, the lives of real-life Gordon Gekkos like Donald Trump were glamorized in mainstream culture and the media. Meanwhile, Democrats were just a bunch of wimps, losers, and stiffs like Michael Dukakis, gloomy naysayers who fretted about the rising national debt instead of enjoying the great American comeback.

1990s: A masterclass in the co-option of cool. Bill Clinton took what was coolest about Ronald Reagan - charm, optimism, and new ideas - and brought them to the Democratic side. He played the saxophone, spoke to ordinary Americans about their pain, and reassured the nation that he was a "New Democrat"; not like the tired old ones. In so doing he won over half the nation, while the other half looked on bitterly at his electoral and economic successes. Their anger at Clinton ultimately culminated in his farcical impeachment by prurient ideologues and repressed sex-obsesseds, first among them Special Counsel Kenneth Starr, who was about as uncool a person as is humanly possible.

2000s: After 9/11, partisan politics were put aside as the nation rallied around the flag. Rudy Giuliani, the socially moderate NYC Mayor popular among members of both parties, was definitely one of the cooler politicians. Once the Iraq War became a quagmire, however, George W. Bush became very uncool, widely loathed at home and abroad. Barack Obama, on the other hand, effortlessly exuded coolness from the moment he began his presidential run in 2008. Not only was he way cooler than Bush and McCain, he was also so much cooler than his main primary opponent, the perennially uncool Hillary Clinton (unlike her husband). Libertarianism also had its moment in the sun at the end of the decade, as part of a spectrum-wide backlash against Bush-era neoconservatism.

2010s: Obama's cool sheen began to wear off early in the 2010s, but no matter what he would always be way cooler than his enemies, especially when organized into a group so utterly uncool as the Tea Party. In other words, when the main conservative opposition to your administration consists of a legion of Glenn Beck fans dressed in comically absurd Americana outfits, it's really no contest. Up-and-coming congressional conservatives like Michelle Bachmann and Ted Cruz were equally, if not more, unlikable. Somewhat unexpectedly, the 2016 election saw young left-wing activism become the coolest it had been since the 1960s through the campaign of Bernie Sanders, one of the hippest campaigns of modern times, only to lose in the primary to the forever uncool Hillary Clinton. On the Republican side, nominee Donald Trump still perhaps had some lingering 1980s coolness here and there, but the supporters he attracted were not very cool types. The idea of a "Trump supporter", which emerged during and after 2016, was supremely uncool to anyone not among the converted. Disproportionately old, white, bigoted, and rural, to anyone but themselves the "Trump supporter" represented the least cool segment of American society. This perception only increased after the riot at the US capitol (2020s, but whatever), which made even many Republicans embarrassed and ashamed at what their party had become.

Flawless analysis, and highly detailed.

[Schiff for Senate]

Now?

The coolest Republican is Adam Kinzinger - who most of the party considers to be a RINO...
On the other hand, the most beloved figure in the party is a twice-impeached ex-president who was so bitter about his loss he refused to expect it and tried to have his cult invade the capitol of his own country. Less cool, and more concerning/disturbing/psychotic.

[Schiff for Senate]

Now?

The coolest Republican is Adam Kinzinger - who most of the party considers to be a RINO...
On the other hand, the most beloved figure in the party is a twice-impeached ex-president who was so bitter about his loss he refused to expect it and tried to have his cult invade the capitol of his own country. Less cool, and more concerning/disturbing/psychotic.

What about Schwarzeneger?

Very true, but both Kinzinger and Shwarzenegger are considered RINOs at this point. Ironic that two of the coolest and best figures left in the party are so disliked and distrusted there.

[Schiff for Senate]

Now?

The coolest Republican is Adam Kinzinger - who most of the party considers to be a RINO...
On the other hand, the most beloved figure in the party is a twice-impeached ex-president who was so bitter about his loss he refused to expect it and tried to have his cult invade the capitol of his own country. Less cool, and more concerning/disturbing/psychotic.

What about Schwarzeneger?

Very true, but both Kinzinger and Shwarzenegger are considered RINOs at this point. Ironic that two of the coolest and best figures left in the party are so disliked and distrusted there.

Kinzinger is not 1/10 as cool as Arnold

Fair enough. I can't believe I forgot Schwarznegger. I agree with you - the Governator is cool on his own level.