Because their aim is to take over society, for decades, the Left has cultivated "coolness".
The Left has used every mass media tool and trick in the book to make youths associate left-wing policies with "coolness".
It's cool to be subversive, anti-establishment, pacifist, "green", anti-American, anti-Puritanical, anti-Founding Fathers, anti-nuclear - anti-"nuclear FAMILY", anti-religion, anti-"big business", anti-talk radio, anti-hunting, anti-NASCAR - and so on.
The Left's desire to be associated with young, attractive and popular ACTORS and MUSICIANS -- (not the sharpest folks or most educated folks in the world, GENERALLY!) -- is a clever marketing TRICK.
And the Left uses the converse, too - caricaturing people on the right as dumb oafs: SNL's depiction of Palin, the entertainment industry's and MSM's depiction of Dubya, and Reagan before that.
The point being to reinforce the idea that leftness is smartness/chicness/COOLNESS and rightness is dumbness/oafishness.
The truth is the left-wing ideas have NOT helped humanity ANYWHERE as well as right-wing ideas have: China had 40 years of Mao-ness and it was an awful impoverished era; it only took 2 decades of A LITTLE rightness (a little free market capitalism) for China to go from starving poverty to fat affluence; 300 MILLION people were lifted pout of poverty by "right-wing" policies. Comparing North and South Korea leads to the same conclusion. Ditto East/commie Europe (from 1945-1989) and Western Europe. And everywhere else you want to compare: freer more 'right-wing" societies offer their people better living standards, longer healthier lives - AND MORE LIBERTY - it's a win-win-win! ((No coincidence here: prosperity is a by-product of liberty!)
All the chic and cool tools and toys of the modern world are the products of right-wing policies: compare Soviet cars to Detroit's of the same era; commies cars sucked; Detroit's were cool --- (and as bad as Detroit's were, they were better than Moscow's!).
I think the way out of this is manifold:
FIRST: the right needs to expose the hypocrisy of the champions of left-wing policies: Gore has a huge home and flies by jet EVERYWHERE; Tom Friedman has a SASQUATCHIAN home and flies everywhere; ditto Kennedy and Kerry-Heinz, and Soros.
We need to get personal on this front - perhaps assign people to chase these folks all the time while wearing ridiculous outfit which reinforces their hypocrisy - maybe a PIG outfit.
SECOND; we need to recruit famous media celebrities --- A VERY DIVERSE BUNCH! --- to speak out - like Bruce Willis, Jon Voight, Ted Nugent, Kelsey Grammer - and Vaclav Havel and Ayaan Ali Hirsi, and Jackie Mason and Hank Williams JR, and make a terse/funny 1 minute commercial that can be aired ubiquitously, all the time EVERYWHERE. Maybe even toss in a clip of Reagan and Thatcher and Churchill (and maybe even John Wayne and Jimmy Stewart and Clark Gable being swash-buckling!).
THIRD, we need to boycott things which promote left-wing policies or left-wing celebrities and we need to support products and celebrities which promote right-wing policies. We need to make the bottom-lines of lefties suffer and the bottom-line of righties prosper. This shouldn't be that hard to do; we outnumber them -and box office already proves that their left-wing crap doesn't really sell that well: "anti-war" movies proliferated during the Iraq War, but they all BOMBED! We also need to buy a share in the media companies which produced this left-wing crap and then complain to the Board of Directors!
I think if all these things were done that then the atmosphere would gradually change and even more "cool celebrities" would find the courage to speak out and let people know that they're right-wing.
And then, the battle is almost won. (We'd still have the battle on college campuses to be won: MAKING COLLEGE FACULTIES POLITICALLY DIVERSE!).
When we've won on these two front then we've killed the left: without the chic celebs of the MSM and without pervasive college indoctrination the left would lose the youth and wither away. 'Cause when most people get older, they get wiser and more conservative. (By a HUGE plurality, most young voters voted for Obama - and leftie candidates before him. When many of these young-left voters get older, they tend to vote GOP -- LIKE ME!)
We need to wise up these people sooner, and IMHO, giving them media icons they can admire will do the trick.