ISIS is a disgrace. In recent months, it has slaughtered hundreds of defenseless Iraqi soldiers and Shiite civilians, gunning them into trenches. It has raped and enslaved hundreds of women. It has brutalized children by forcing them to watch scenes of horrific cruelty and violence. It has presided over public crucifixions in its stronghold of Raqqa, Syria. And, of course, it has staged the executions of James Foley, Steven Sotloff, David Haines, and Alan Henning.

But is ISIS also funny? Or, rather, can it be made funny? The Lebanese satirist Karl Sharro evidently thinks so. Taking inspiration from a CNN report this fall on the “anatomy of ISIS,” Sharro produced his own sketch of the group’s hierarchy, lampooning its intricate and austerely demarcated offices:

Sharro’s chart was widely shared online and proved a big hit with the U.S. State Department’s Center for Strategic Counterterrorism Communications (CSCC), which in recent months has been using its own brand of mocking humor as part of a social-media campaign to counter ISIS’s online propaganda. The Center was among the 800 Twitter users that approvingly retweeted Sharro’s chart. Alberto Fernandez, the coordinator of the CSCC, told me that “sarcasm and humor can be very powerful tools against bloodstained criminals like ISIL,” adding, “but you better actually be funny if you want to be effective. Not easy to do.”

Sharro isn’t alone in satirizing ISIS—similar efforts are underway everywhere from Iraqi sitcoms to Kurdish music videos to Saturday Night Live. “Sometimes, you have to mock, to belittle. Because sometimes, belittlement is your enemy’s greatest fear,” commented the Libyan-American writer Hend Amry on Twitter. Amry was referring to #ISISMovies, a hashtag that briefly took off in mid-August:

Earlier this summer, the Palestinian comedy TV show Watan ala Watar produced a segment mocking Islamic State fighters as ludicrous hypocrites. The show was also scathing about the group’s regional politics, suggesting they are detrimental to everyone’s interests, except Israel’s.

Humor can be a potent weapon of subversion. “The literal mind,” Christopher Hitchens points out in his Letters to a Young Contrarian, “is baffled by the ironic one,” and “the sharp aside and the witty nuance … are the one thing that pomp and power can do nothing about.” By way of example, Hitchens refers to the British novelist P.G. Wodehouse, who was captured during the German invasion of France in 1940 and enlisted to support the Nazi propaganda effort. Speaking on Berlin radio, Wodehouse sarcastically observed, “Young men starting out in life often ask me—‘How do you become an internee?’ Well, there are various ways. My own method was to acquire a villa in northern France and wait for the German army to come along. This is probably the simplest plan. You buy the villa and the German army does the rest.” “Somebody,” Hitchens writes, “must have vetted this and decided to let it go out as a good advertisement for German broad-mindedness.”

In his classic study of social movements, Hans Toch describes the “political joke” as “a traditional vehicle of cautious opposition, served to express hostility to the movement.” The power of such a joke, in other words, often lies in its subtlety, its elusiveness, its deniability—though these very qualities may also limit its power. In Wodehouse’s case, it isn’t clear whether the novelist or the Nazis, who appropriated his sarcasm for their own propagandistic ends, had the last laugh.

Karl Sharro would likely appreciate Wodehouse’s use of subversive irony, as would the brilliant satirist Chris Morris. In his 2010 movie Four Lions, Morris takes on the issue of jihadist suicide bombing, subjecting it to cheerful scorn by showing just how ridiculous it is. The movie follows five wannabe jihadists on their quest to strike a blow against the “kafir bastards” of Britain. In the tradition of Chaplin sending up Hitler, Morris portrays his characters as more fumbling idiots than crazed fanatics.

But, equally, humor can be reactionary and put to demagogic purposes. “Laughter can be … an essential element in mob conduct and is part of the background noise of taunting and jeering at lynchings and executions. Very often, crowds or audiences will laugh complicitly or slavishly, just to show they ‘see’ the joke and are all together.” This is Hitchens again, making the essential point that humor often appeals to rank prejudice and herd instinct.

Humor also has an intimate and unsettling relationship to violence, because violence can be funny. People don’t like to admit this, because it undermines their self-proclaimed civilized values and sense of decency, but its truth can scarcely be doubted. Consider, for example, the notorious ear-cutting scene in Quentin Tarantino’s Reservoir Dogs. Having taken a cop hostage after a bungled robbery at a jewelry store, Mr. Blonde informs his captive that he will now torture him, “not to get information,” but because “it’s amusing to me, to torture a cop.” Sadistic violence—violence for its own sake or for the sake of pleasure—is a terrifying prospect for most people. But before the wet stuff, there will be fun. Mr. Blonde turns on the radio, out of which blasts Stealers Wheel’s “Stuck in the Middle With You.” He starts to dance, performing a show for his hostage—and for us, the enraptured audience. Then the violence starts, culminating with Mr. Blonde speaking into the cop’s severed ear: “Was that as good for you as it was for me?” The first time I watched this scene was in a crowded movie theater in Cambridge, and I remember the whole audience—packed with earnest and upstanding undergraduates—breaking into riotous laughter. And there was nothing slavish about it.

Death can be funny as well. Consider this harrowing recollection by former U.S. Marine William Broyles of the dead soldier he encountered during his service in Vietnam:

After one ambush my men brought back the body of a North Vietnamese soldier. I later found the dead man propped against some C-ration boxes; he had on sunglasses, and a Playboy magazine lay open in his lap; a cigarette dangled jauntily from his mouth, and on his head was perched a large and perfectly formed piece of shit.

I pretended to be outraged, since desecrating bodies was frowned on as un-American and counterproductive. But it wasn’t outrage I felt. I kept my officer’s face on, but inside I was ... laughing. I laughed—I believe now—in part because of some subconscious appreciation of this obscene linkage of sex and excrement and death; and in part because of the exultant realization that he—whoever he had been—was dead and I—special, unique me—was alive. He was my brother, but I knew him not. The line between life and death is gossamer thin; there is joy, true joy, in being alive when so many around you are not. And from the joy of being alive in death’s presence to the joy of causing death is, unfortunately, not that great a step.

I recently wrote and abandoned a short satirical piece on ISIS’s savagery. It centered on the testimony of Majid, a disgruntled former member of Al Hayat, ISIS’s media arm, who had been sidelined due to his extremism. He’d won accolades for his proposal to film ISIS fighters raping captive women (even though the men were unable to perform sexually on camera), but his brothers-in-arms had recoiled at his proposal to dangle prisoners over a shark tank.

But I couldn’t bring myself to publish the piece. Sure, it was meant to be subversive, because it derided ISIS’s hyper-masculinity and the permissiveness with which it interprets Islamic sources. But it was also extraordinarily offensive, because ISIS is raping Yazidi women and selectively invoking Islamic theology to justify the practice. And it is filming its depraved deeds, including the stoning of women accused of adultery. It has not, as far as I’m aware, filmed rapes for propaganda purposes, but it could yet do so. Joking about such a prospect seemed off-limits because it was too close to the bone. It simply wasn’t outlandish enough.

These considerations, however, greatly limit the comedic bounds surrounding ISIS. The group’s outstanding feature is its extremity: its unabashed moral nullity, its willingness to do anything in pursuit of its holy mission, its troglodytic squalor. We can certainly make fun of ISIS, but its very outlandishness narrows the scope of humorous material.

There must be, as Chris Morris well understood by making his jihadists dress up in explosives-packed bird costumes, an appreciable distance between satirical portrayal and solemn reality. The chief problem with ISIS in this regard is how it has compressed the distance between the real and the fantastical.

“The sophisticated element in humor,” writes Hitchens, “is exactly its capacity to shock, or to surprise.” The challenge for satirists of ISIS is that it’s the jihadists who are pushing all the boundaries and doing all the shocking. And for ISIS’s victims, it isn’t remotely funny.