Over the weekend, Larry David made headlines—and waves—for his opening monologue on Saturday Night Live. Probably the most provocative of his jokes was the one where he noted that, if he had been a concentration-camp inmate, he’d likely have been checking out some of his fellow prisoners. It’s easy to imagine this as another Larry David life-imitates-art special, an echo of the current season of Curb Your Enthusiasm: The real David goes on a late-night comedy show and says something that gets him into trouble, with the slings and arrows of social media replacing the Iranian fatwa placed on his character in the series.

But David’s joke raises serious age-old questions about the use of controversial topics for humor in general and about that excruciatingly powerful case in point, the Holocaust, in particular. Is the Shoah ever appropriate to joke about? And if so, is this one of those justifiable cases? Having just published a history of Jewish comedy that ranges from the Bible to Twitter, a book in which David plays no small role, maybe I can offer a broader perspective on the matter. Considering humor through the lens of “appropriateness” often involves a kind of moral evaluation. As David’s work and the larger canon of Holocaust comedy reveal, the way a joke on the subject is received can sometimes rest on its ethical stance.

First, it should be noted that no one who has followed David’s groundbreaking and taboo-challenging career should be surprised by his SNL monologue. In his 1999 hour-long special for HBO, David had a line about admiring Hitler because “he wouldn’t take any shit from magicians.” The show he co-created with Jerry Seinfeld was literally responsible for mainstreaming Nazi as a descriptor (viz., “soup”). And Curb, the show that bears his auteur imprint most fully, started its run with Larry calling his wife “Hitler” in the pilot, and only went further from there.

In one episode, Larry, who’s the co-owner of a restaurant, continues to employ an obscenity-screeching chef with Tourette syndrome out of the mistaken belief that he had spent time in a concentration camp. (What Larry thought was his tattoo turned out to be a lottery number the chef had written on his arm.) In another episode, viewers are treated to a dinner scene where a Holocaust survivor faces off against a contestant from the reality competition show Survivor. Throw in the season-long arc where Larry stars in a Broadway production of that seminal work of American Holocaust humor, Mel Brooks’s 1967 film The Producers, and you realize just how much space Curb has devoted to the topic.

But it’s instructive to look at the differences between David’s and Brooks’s approaches. A World War II veteran, Brooks created a work that was aggressive, pugnacious, and anti-anti-Semitic: He’s said on many occasions that his reason for portraying the Nazis was in order to cut them down to size. Nonetheless, the original Producers movie is at its core all about the issue of whether or not an audience would accept a work like The Producers and the kind of comedy it offered. Consider the reactions of the horrified audience at the premiere of Springtime for Hitler, the fictional musical at heart of the story: Only when viewers realize the show is mocking, rather than sympathizing with, its subject (“It’s funny!” someone calls out) can it be accepted and become a hit. In short, Brooks’s film employs the Holocaust for reasons the Anti-Defamation League would find acceptable, even if the group might disagree with the methods.

Morality, of various sorts, pervades varying strains of Holocaust humor, most notably the comedic art produced by those who lived through it. Whatever the truth of David’s remark on Saturday night that “there are no good opening lines in a concentration camp,” there were indisputably jokes swapped in the latrines at Auschwitz and in cabarets in Theresienstadt that may have served the purpose of psychic resistance or resilience. But a part of the reaction to David’s concentration camp joke, perhaps, comes from one of the wellsprings of his uncomfortable comedy: its amorality.

Whether it’s through his Seinfeld alter ego George Costanza or his character on Curb, David thrives on presenting himself as deeply unlikable, a magnet for hostility. Part of that anti-appeal—as seen in countless episodes of Seinfeld and Curb’s “Palestinian Chicken” (in which Larry happily sleeps with a beautiful woman who hurls anti-Semitic abuse at him in bed)—is the David surrogate’s willingness to tolerate debasement if it involves the satiation of his lower desires. Watching these antics is often supremely cringeworthy for viewers, if not for the character himself.

In this sense, David’s SNL joke is not precisely about the Holocaust; rather, it is the ne plus ultra of the sort of humor his alter egos embody: What is the most inappropriate and extreme situation in which this sort of thing could occur? But because the joke is using concentration camps as a throwaway—rather than thinking or feeling deeply about it, or using it for other arguably principled purposes—it’s easy for viewers to think, You’re invoking this? Just to get a laugh for that?

David’s humor doesn’t always treat the Shoah so lightly. For example, his SNL line is the opposite of the brilliant aforementioned survivor/Survivor joke, where the reality-show alumnus Colby Donaldson, playing himself, trades suffering narratives with someone who went through Hitler’s hell. In that Curb episode, David is searchingly moral, flaying a kind of ethical vacuity and historical relativism about the Holocaust. If a reality-show contestant can complain to an Auschwitz survivor about the struggle of not having snacks on set, the extent to which his obliviousness feels familiar to viewers may reflect the Holocaust’s receding capacity to disturb.

But that thought-provoking Curb episode aired in 2004, and this is 2017, and after Charlottesville. David’s invocation of the concentration camp on Saturday as a kind of peekaboo provocation—kidding/not kidding; comedy is tragedy plus time—might ring particularly hollow in an America where neo-Nazis march openly on the streets and white-nationalist memes proliferate online. Restaging The Producers now, I suspect, would raise a different set of issues than it did when the Broadway musical debuted in 2001. One of the questions that haunts all comedy of offense—“too soon?”—has been revealed to be a tragically mutable concept. Discomfort with David’s joke may not just come from the fact that it highlighted a kind of inappropriate amorality sometimes present in his comic sensibility; it may also be that he accentuated an old question’s fresh moral urgency.