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

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 It's not even that they're outdated—most of us in the Internet generation don't expect boomers to know every video on WorldStar.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.

3. Huckabee vs. Norris

During the 2008 election, there were a lot of unlikely pairings, but action-film king Chuck Norris and Mike Huckabee might have been one of the least likely. Which is not to say Chuck Norris is particularly cool—he’s more of a reminder of what the culture most valued during the Reagan ‘80s, which was muscular white dudes wielding AKs and dodging explosions in the name of America. But that’s exactly what Huckabee was going for: a little Reagan cred to be able to stand up to war heroes like his opponent John McCain, and when it was time to cut an ad supporting his more “rugged” policies he recruited Norris and tried to make it cheeky. His immigration policy? “Two words: Chuck Norris.” Wow, Huckabee. Not only are you corny, you are also implying that immigrants are inherently “bad guys” for Norris to chop down with martial arts or something? Meanwhile, the right-wing media totally missed out on the outtakes: Norris and Huckabee doing a self-conscious “terrorist fist-bump” a full year before Fox News attacked Barack and Michelle Obama for theirs. (Which, of course, was what those of us in the waking world call a "pound." Don't these people ever watch sports?)

4. Dan Hughes Gets It!

Hughes is the Republican challenger to California incumbent senator Dianne Feinstein, and despite the title of his latest campaign video, he does not in fact "get it." The video begins with California Republican Chuck Devore explaining why he supports Hughes' campaign. Which would be nothing out of the ordinary, except for the way it is filmed: with awkward, purposely low video and audio quality, so that it comes off like VHS footage unearthed from someone's basement. Next, Hughes' disembodied torso pops up out of nowhere, to the sound of a tinny, pre-programmed '80s hip-hop beat, to let us know he approves this message... and then little .jpegs of flying eagles float by. The bad production quality and insanely cheesy effects and video clips are purposely meant to come off like a cross between a retro YouTube meme and SNL Digital Short. At first you might think his campaign is purposely trying to sabotage him—particularly when an eagle's head pops up and says "oh yeah" in autotune, in front of an explosion. But the corniness is in fact a baldfaced attempt to get the video to go viral so that young voters will support him on the strength of being cool or, more intentionally, ironically "getting it." Of course, younger voters can see through such blatant marketing—we may love kitsch, but we're not stupid. Meanwhile, though, it might be that the joke's on Dan Hughes: his campaign site looks like it was built in 1999, in C+, with PaintShop. Maybe he’s going for an overall ironic-retro cool thing? It’s so confusing. What’s not confusing: his political views hearken back to about 1959.

5. Mitt Romney vs. More Rap Slang

Mitt does it again—and this time the writers at Letterman were complicit. When Romney read the Top Ten Countdown during the GOP primary, he introduced himself by saying, “What up, gangstas? It’s the M-I-Double-Tizzle.” Presumably that was in the script to mock his completely awkward use of retired rap slang in the past, but even in the context of a joke, it didn’t get any less weird, particularly since Romney seems incapable of believable self-deprecation, his forced wooden smile never wavering. Meanwhile, while most probably think the “izzle” suffix is an old ‘90s Snoop Dogg-ism, it’s actually even older than that, having originated with the Gap Band in the early 1980s. Just a hunch, but we’re betting Romney didn’t really bump the Gap Band in the early 1980s. But if it helps his street cred, Eminem has a track dissing Cranbrook, the fancy private school Romney attended. (Hint: it does not help his street cred.)

6. Republicans vs. Most Musicians

Judging from years of campaign songs, most politicians have terrible taste in music regardless of their affiliation, though Republicans tend to lean toward like-minded artists. When they choose any music that’s made by actually cool (or even semi-cool) people, however, they usually end up with cease-and-desists. When Romney tried to use the song “Wavin’ Flag,” by progressive political rapper K’Naan—who emigrated to Canada to escape civil war in his home country of Somalia—the song was immediately pulled by the rapper, who felt Romney’s views were diametrically opposed to his own. (Added blow: K’Naan said that if Obama would like to use the song instead, he’d gladly grant permission.) This New York Times piece has a good overview of the history of Republicans getting dissed by musicians, with a list that includes Talking Heads innovator David Byrne, Heart sisters Ann and Nancy Wilson, and Tom Petty. Of course, the reason so many popular and forward-thinking musicians won’t be associated with the GOP is that the GOP is so hostile to progressive causes, which a large majority of artists support. It’s a telling point, and one they should heed. If Republicans want to be truly cool, they’re going to have to change their entire plizzatform.

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