Could there be more target-rich comedic terrain than today’s Left? From the inane brain droppings of Hollywood sages to elite colleges that offer courses on cross-dressing, from Obamacare to Al Sharpton’s gall in presenting himself as an ethicist, material mocking progressive absurdities and hypocrisies should be standard fare in comedy clubs nationwide and at every stop along the college circuit. That it’s not happening—to the contrary, that it is Republicans and conservatives that are almost always targeted by political comedians and portrayed as self-interested haters, mean-spirited prigs, and all-purpose stiffs—is part of a larger problem: the refusal of so many on the right to acknowledge the profound influence of popular culture in forming attitudes and values.

Believing that ideas are (or at least should be) paramount, and imbued with contempt for (or at least profound indifference toward) much popular culture to start with, conservatives have ceded the field to the other side without a fight. From Hollywood to People magazine, liberals relentlessly churn out mass culture reflecting their worldview, but conservative pushback has mostly been confined to a single cable network and a handful of think tanks and smaller idea-driven magazines and publishing enterprises. Yet, arguably, on no front has the Right’s preemptive surrender been more costly than in the realm of comedy, which has come to play such a vital role in shaping the views—and the voting habits—of the nation’s young. Though a handful of Southern comedians such as Jeff Foxworthy, Larry the Cable Guy, and Bill Engvall have done well, their appeal is expressly to a Red State audience. Even the more mainstream comics skewing right—reformed liberals Dennis Miller and Adam Carolla—play mostly to a conservative audience. So, if only by dint of appearing almost exclusivey on Fox, does arguably the quickest wit on TV today, Greg Gutfeld.

Why, in a country at least as red as it is blue, are there no conservative comedians of general renown and broader demographic appeal? Why no right-of-center Bill Maher, whose long-running HBO show is given over to endless sneering put-downs of Republicans? Why no conservative Lewis Black, widely celebrated for his over-the-top rants against the Right? Why no conservative Stephen Colbert, whose entire shtick on Comedy Central is a parody of the supposed thickheadedness and pomposity of conservatives? Why, above all, no conservative Jon Stewart, Comedy Central’s smirky master of the befuddled, wide-eyed double take, acknowledged everywhere—and not just by liberals—as our most gifted social commentator?

Nick DiPaolo, a 51-year-old with 20-plus years in the business, will tell you why. A conservative stand-up comic with a tough, no-BS manner to go with a razor wit, DiPaolo brings a unique perspective to the subject. While he’s done a fair amount of radio, recording and TV, (including regular appearances on Gutfeld’s groundbreaking ‘Red Eye,’ which for reasons known only to the cable gods plays on the east coast at 3 AM!), his bread and butter remains the comedy club—catering as it does to the young and allegedly hip, politically “the belly of the beast,” in his words. The problem, he says, starts with how deeply the attitudes of young people have been conditioned by modern education. “The pool,” as he puts it, “has been tainted.” On stage and off, DiPaolo seems incapable of pulling punches. Even when doing neutral material—say, about his marriage or the trials of growing older—his worldview is never far from the surface, evident in his every wise-guy ad lib or comeback to a heckler. As his friend and fellow libertarian Colin Quinn once told him, “You could be doing a bit about McDonald’s and everyone’ll know how you voted.”

By DiPaolo’s own account, when he ventures onto explicitly ideological terrain to mock the Left and its hypocrisies, his young audience is often as stunned as it is entertained. Catch one of his old appearances on the web, and you’ll get the idea. Take, for instance, the Minnesota club date he did in the wake of the Michael Vick dogfighting scandal. When DiPaolo launches into the routine by noting that one of his favorite topics is the refusal of the media to talk straight about race and underclass culture, the place instantly goes silent. “Look how quiet it’s getting,” observes DiPaolo, who then gives voice to the audience reaction: “Holy shit, where’s he going with this? This is going to get ugly!” Where he’s going is that he recently heard a pair of white ESPN announcers discussing the Vick case, declaring that the story had absolutely nothing to do with race. “No, you’re right,” DiPaolo agrees, mockingly. “There’s a lot of white people making $60 million a year having dogfights behind the garage on weekends. Yeah, right now Bill Gates and a bunch of guys from Microsoft have 50 Yorkshire terriers in sweaters yelling, ‘Go get ’em, Bianca! Get him, Fluffy!’ ”

DiPaolo says that at such moments, the laughs he gets are at first tentative and uneasy. “People in their twenties, their brains have been turned to mush from what they’ve been taught in college. They’re afraid to laugh, they know they’re not supposed to. So the trick is getting them to laugh despite themselves, because they know deep down you’re telling the truth.”

Needless to say, this is what much of the best socially conscious comedy is supposed to do: say the unsayable and lay bare society’s self-serving deceptions. Lenny Bruce and George Carlin are revered for having done so, and Richard Pryor remains the model for virtually every one of today’s stand-ups striving to stand out as fearless and—the adjective of choice—edgy. But in comedy, as in other realms of public life where liberalism holds sway, standards come in duplicate and triplicate. “Political correctness stifles only one voice: the white heterosexual male,” says DiPaolo. “I swear, I don’t want to hear another story about the courage it takes for a black or woman comic to talk honestly. Is there anything a female or black comic could say that would get them in trouble? I mean, [popular black comedian] Tracy Morgan actually said, ‘If I had a gay baby, I’d fuckin’ kill it,’ and he still has a career. If I said anything close to that”—he laughs—“let’s just say you’d never see me again.”

So how would he assess the effect of his politics on his career? DiPaolo can’t help but laugh again. “Look, the industry is made up of hard-core leftists. The idiots who run this business, if you make fun of Obama, not only don’t they think it’s funny; they think there’s something deeply wrong with you. They’re offended. I’ve never had a special on HBO, which is ridiculous. The last time I was on HBO was in ’92 or ’93—before I had anything political to say. Years later, Chris Rock hired me to write on a special he was doing over there because I could write his voice—it’s actually easy to write the voice of someone you disagree with politically—but the HBO executives were totally hostile to me.”

This, of course, is another aspect of the problem. The broadcast networks that most effectively showcase comedy enforce a de facto ideological litmus test. But DiPaolo keeps plugging away because he can’t imagine doing anything else and because “if there’s hope for this generation, which I like to believe, comedy may be the only shot we’ve got.”

Still, it helps to keep a sense of humor. “I’m dropped off at a back door, which leads through a kitchen,” he wrote recently of arriving at a club on yet another long night on the road. “The smell of fryolator grease and stale beer permeates the room. I say ‘Hi’ to the Hispanic short-order cook, who can barely manage a nod, even though he’s not busy. I think to myself ‘maybe he heard me do my illegal immigrant bit this morning on the radio.’”


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