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Rapping Republicans? 6 Hilarious Moments When Conservatives Tried -- and Failed -- to Be Cool

Right-wingers often try to shoehorn themselves into pop culture. They almost always fail -- and America collectively cringes.

With American culture on warp speed, thanks to the whirling dervish that is technology, every single person with Internet access can be on top of every pop culture development at all times. Which means nerdy, square politicians occasionally have to shame themselves trying to seem cool. Hence the horror of Republicans attempting to prove their cultural relevance by invoking ancient slang and references, and coming off like a too-big foot trying to fit into a little-ass shoe. It's not even that they're outdated—most of us in the Internet generation don't expect boomers to know every video on WorldStar. (And if they do: what are you doing with your lives, dogs?) It's that almost unfailingly, when right-wingers try to invoke pop culture for their own campaign-serving ends, their outdatedness is coupled with a complete lack of understanding of the context in which said pop culture exists, and often a glaring misunderstanding of anything that is not culturally white.

As awkward candidates like Romney salivate to prove they're relevant, we respect President Obama more for saying he listens to Jay-Z mostly because of Reggie Love. (Also, Michelle Obama can dougie.) Here are the 6 most embarrassing moments of right-wingers trying -- and spectacularly failing -- to be cool. As election 2012 spirals out of control and everyone scampers for the youth vote, ready your eye sockets for vigorous rolling.

1. Romney Lets the Dogs Out

The absolute most embarrassing moment in recent memory, not to mention totally offensive. Mitt Romney, stumping in Jacksonville, Florida, on Martin Luther King Day in 2008, stops to pose with a group of young black constituents. Throwing his arm around a young woman, Romney first asks where the camera is. Then, for absolutely no reason whatsoever, he invokes the Baha Men’s "Who Let The Dogs Out," a song written for Carnival in Trini and Tobago that became a huge, worldwide hit—in the year 2000. (It was a frat-party staple, so it's not inconceivable that Romney learned it from one of his many fratty sons.) After Romney barked out the chorus of the song, a couple of the older kids giggle incredulously, like “Did that actually just happen?” Most of them don’t react, however—because it’s likely that they’ve never actually heard the song—and Romney manages to look uncomfortable with black people and with young people. Double whammy. As one YouTube comment put it, “Romney is the uncanny valley.” Even grosser, at the same event, he said an infant baby wearing jewelry was wearing “bling bling”—more archaic hip-hop slang, which also makes one wonder if he sees every African American as a rap stereotype.

3. MC Rove

A banner moment in Republicans embarrassing themselves into oblivion. In 2007, at the Radio and Television Correspondents’ dinner, then-White House adviser Karl Rove was honored by a rap from the two incredibly unfunny comedians from 1980s relic Whose Line is it Anyway? Of course the joke was a play on his whiteness performing gestures from black culture, which is an awkward trap lots of whites have fallen into (even ostensibly cool Natalie Portman). But it’s even grosser when it’s Karl Rove, who masterminded the covert racism against President Obama in the 2008 election (and, ironically, called him “too cool”), and then finds it prudent to essentially mock (a 1984 version of) hip-hop culture in a room full of mostly white people. It’s bad enough that he’s doing rhythmless white-man dance as a badge of honor, but his b-boy stance (arms crossed around the torso) is shameful. The audience, of course, thinks it is hilarious! Those of us at home sent a million psychic barf noises.