I make a lot of jokes about the Holocaust. It’s something I’ve done my entire life, a sort of evolutionary protective response to the existential sense of dread I felt as a child every time I passed the rough-hewn iron sculpture that served as the Holocaust Memorial at our local JCC. And I’ve gotten really good at it over the years.

A few months ago, I had an entire room at my office in stitches over an impromptu routine comparing the amenities of several second- and third-tier concentration camps (and believe me, it takes many years of refinement to get to a place where “Sachsenhausen” is an effective punch line, but now I’ve got it.) As the merriment continued, a non-Jewish colleague who is pretty damn funny herself, lamented: “I just can’t make those jokes. I can’t be funny about the Holocaust.”

I’m an inclusive person, and I protested: Sure she could. She demurred, I kept encouraging her. And a couple of days later, she busted one out. I don’t remember what it was about, except it probably had to do with Auschwitz and it fell flat as a stone. Not so much as a titter. The joke was funny, she is funny, but the joke wasn’t funny with her telling it. She was right, and I was wrong.

So this is what I found myself thinking of during comedian Natasha Leggero’s recent appearance on Conan, in which she described her conversion from Catholicism to Judaism upon marrying fellow comedian Moshe Kasher (who has written at length about his Orthodox upbringing and his father’s conversion to the Hasidic Satmar sect.)  In a jokey, punch line-heavy segment, Leggero (who, for the record, I have always found very, very funny) talked about Judaism’s relatively liberal attitudes towards abortion. “You could get an abortion on every Jewish holiday and it would be OK,” she told the late-night host, adding that her conversion classes consisted of “genuine seekers” and “young beautiful women being forced to go by their older fiancés with turkey necks.”

Leggero’s jokes don’t rub me the wrong way. And I would never say that Leggero’s conversion to Judaism is anything but deeply felt and genuine. I don’t care one way or another, frankly. I’m not a religious or reverent person, and I don’t particularly feel that others need to be. But, for some reason, I didn’t laugh—and it’s not that the jokes aren’t funny. They have potential. But Leggero—who is typically a riot—isn’t funny telling them, much like my aforementioned Auschwitz-joke-telling friend.

If Sarah Silverman had uttered the same jokes, I imagine I would’ve rolled in the aisles (or on my living room floor, because that’s where the TV is), but out of Leggero’s mouth, there was simply too much of a twinge of Tim Whatley. You know, Tim Whatley, the Seinfeld dentist (played, of course, by the pre-Breaking Bad Bryan Cranston) who converted “just for the jokes.”

I’m not sure why this should be—that some Jewish jokes fall flat out of some mouths, but can absolutely slay a room out of the mouths of others. Maybe it’s because the essence of Jewish humor comes from having a lived Jewish experience, which traditionally means having had to live and come to terms with a religion and ethnicity that, due to centuries of oppression and prejudice, you have not exactly freely chosen if, you know, given the option. A person who just converted? The whole Jewish suffering thing may need to sink in a little bit. Leggero will get there, of course. She’s funny and smart and obviously knows plenty of Jews willing to help her find that perfect soupcon of wry self-loathing that is our people’s indelible gift to the world. It might take 19 four-hour classes to convert to Judaism, but being Jewish? That’s the work of a lifetime.

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