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Milo Yiannopoulos’s provocative speech is similar to predecessors such as comedian Andrew Dice Clay, but with the added danger that people sometimes take him seriously.

The era of crude nineties comedy may have left, but professional trolls still cling to it for shock-value defences of free speech

Of all people, even Andrew Dice Clay, the 59-year-old self-appointed "Heavyweight King of Comedy," has little love for U.S. President Donald Trump. "We got Donny T. in the White House! Guy stole my whole shtick!" Clay huffs, dressed in an embroidered leather trench coat and sunglasses so oversized they could double as welding goggles.

Clay (a.k.a. Dice, the Diceman etc.) then went on to bait the soused crowd of the Tropicana Hotel's Las Vegas Laugh Factory last week with a revision of his most famous bit, imagining what it would sound like if Trump recited a series of revised children's nursery rhymes so dirty and intentionally offensive there's no way they can be reprinted in a family newspaper. The bulk of the crowd hooted and hollered, brusquely harmonizing with Dice when he delivered his trademark punchline exclamation, "OH!" But my friends and I – who bought tickets because … why, exactly? Morbid curiosity? The hipsterish hope that it'd be so bad it's actually, somehow, good? Plain old self-loathing? – just shot bored, quasi-uncomfortable looks at each other.

Andrew Dice Clay attends the premiere of Warner Bros. Pictures' Entourage at Regency Village Theatre on June 1, 2015 in Westwood, California. Getty Images / Jason Merritt

More than tedious and unfunny, an Andrew Dice Clay stand-up set is, circa 2017, mostly pathetic. Here was a guy who, in the late eighties and early nineties, raised genuine hackles with his hyperbolic, bad-boy persona. He was banned by MTV, and boycotted by Saturday Night Live cast members when he guest-hosted the show in 1990. Also in 1990, Clay famously earned the title of being the first comedian to sell out New York's Madison Square Garden for two consecutive nights.

Now he's reduced to shuffling around a Vegas stage, his act marked by its total pointlessness. "It's no Madison Square Garden!" chirped one audience member. And indeed it wasn't. What we were witnessing was a fall from, well, not quite grace, but … the opposite of grace. A fall from crudity? Is that a thing?

This unremarkable image of a formerly feared menace to good taste bubbled back into my brain a day later, when prominent "alt-right" agitator and "free-speech fundamentalist" Milo Yiannopoulos had his book deal nixed by Simon & Schuster. A proud racist, anti-feminist, Islamophobe, transphobe and self-styled wannabe-agent provocateur, Yiannopoulos (or just "Milo") is the true inheritor to the Diceman's archly antagonizing shtick.

The super obscene rock-star comics of the eighties and nineties (Dice, Sam Kinison, even Eddie Murphy) have mutated into the bloviating cable-news and college-campus insult pundits of the Milo, Ann Coulter and Bill O'Reilly mould. One of the more cockamamie theories to emerge in recent years in the United States's conspiratorial underground is that barking-mad InfoWars pundit Alex Jones is actually legendary Texas comedian Bill Hicks, who allegedly died in 1994 but was actually recruited by the CIA to serve as the "controlled opposition" to the mainstream media. The theory unravels when guys such as Alex Jones now, bafflingly, constitute the institutional press carrying water for the Trump administration.

Granted: Milo is his own beast, cut from a different cloth than Clay – the latter clad in the studded leathers of hyperbolic Brooklynite masculinity, the former essentially a caricature of his own campy homosexuality. Dice makes jokes about choking his wife unconscious during sex. Milo rouses his followers by announcing that homosexuality is aberrant (despite being himself a gay man), that "feminism is cancer," that terrorist attacks embody "mainstream Muslim values" and that the Black Lives Matter movement is a "hate group." But the two are the same in their desperation to seem edgy, to offend as if offending were somehow a virtue in itself. Both thrive on a perverted, inverse logic that suggests that the things they say are funny, or legitimate, precisely because some invisible arbiter of cultural permissibility doesn't want them to be said.

Milo Yiannopoulos holds a press conference in New York on February 21, 2017.

As a comedian, Dice's provocations can be more easily explained away. After all, these are "just jokes." He has acknowledged that his Diceman persona is an intentionally obnoxious "macho moron," and it's possible to argue that his ultra-offensive, brutally alienating 1990 double album The Day the Laughter Died works as an intentional piece of pure provocation that borders on art. By contrast, Milo is a writer, speaker and op-ed talking head who's afforded a certain seriousness, despite the risibility and incoherence of his thinking. He is a professional troll, whose danger is that he actually means – or at least pretends to mean – all the execrable things he says.

The comedian has a way of lassoing and purging an audience's worst instincts, even if it's just through the catharsis of laughter. The troll rallies and emboldens these same instincts. A comedian can shed their persona as easily as unbuckling an enormous leather duster. The troll wears irony, rancour and nihilistic antipathy like a second skin Krazy Glued to their epidermis. So while it's impossible to imagine Dice's fans, even at the peak of his unlikely fame, rioting in the streets to advocate for the return of oldfangled gender relations, Milo attracts aspiring politicos to spread his message of social and political regressivism and hate, dressed up in the garish cloth of "cultural libertarianism."

If there was any infinitesimally small, microscopic token of encouragement to be found watching Clay, it was in precisely how irrelevant it seemed. Here was a possible future for Yiannopoulos, the United States' current reigning cartoon bad boy: entirely disconnected from the social world around him, half-heartedly uttering hate speech while boozy out-of-towners yuk it up and rueful ironists scan each other's faces for some sign that this is good or fine or even just okay.

Like Clay in the nineties, Milo is now seen by some as vanguardist, defending the value of freedom of speech at its furthest, least tolerable limits. But the thing about free speech being constitutionally enshrined is that you don't have to use it. It won't just disappear. In his own weird, sad late-career way, Clay proves this.

Chain-smoking on a Las Vegas comedy-club stage, Dice had tumbled a long way from the heights of riling up sold-out crowds in a downtown Manhattan arena. But after decades of controversy, and sea-changes in social mores, he's still free and able to ply his trade, such as it is. There's just less of an expectation that the culture as a whole would be shocked by it, or even all that interested in it. To use a Diceman-ish vulgarism: Exercising freedom of speech is like that old maternal wisdom passed down from mothers to teenage sons caught with their hands down their pants. You don't have to clutch the thing constantly. It's not like it's gonna fall off. OH!