At some point in their late teens and early 20s, a lot of people—women too, but especially men—decide that being dark and edgy is a pretty good substitute for an actual personality. They think they’re smarter than everyone else because they’ve read a little Doestovsky and watched some Bill Burr, and are absolutely convinced that the best way to show that The Void doesn’t scare them is to crack endless dead baby jokes. Yeah, especially that one involving a microwave. 

For most people, the impulse to crack edgelord jokes—where offensive shock is the punchline—goes away about the same time they stop wearing all black, get a job and realise that they’re not professional comedians. Except, of course, some of them are standup comedians. From Lenny Bruce to Bill Burr to Ricky Gervais, comedy is full of artists who have taken “pushing the envelope” to new heights, sometimes to make a point and other times just for the childish puerile joy of it. 

And sometimes, they’ve pushed so far that they broke through the envelope and landed right into hot water. It’s probably not the best idea to joke about a mass shooting that killed 25 people the week that it happened like Dana Cook did in 2012. Or to make a rape joke nine months after you admitted to masturbating in front of women who felt coerced into staying, like Louis CK did. 

The key to getting away with edgy humour is to know your audience, know the context and, sometimes, know when to keep your mouth shut. So here’s our pick of seven times comedians went for the darkest, edgiest punchline and got it right (or at least were lucky enough to get away with it). 

1. Anthony Jeselnik on Disasters

Anthony Jeselnik is often called the Dark Prince of Comedy, thanks to his single-minded obsession with “find[in] things that you shouldn’t joke about, and find[ing] a way to make a joke.” Over four albums, a number of Comedy Central roasts and two seasons of The Jeselnik Offensive, he’s stuck to his guns, cracking jokes about death, disability, the Holocaust and abortion. But one of his darkest joke is his bit on—uh oh—the same 2012 cinema shooting in Colorado that got Dane Cook in trouble. Jeselnik treats disasters as a ‘Get Yourself Cancelled’ challenge and somehow comes through unscathed. 

2. Sarah Silverman’s Dangerous Bait and Switch

Sarah Silverman has a well earned reputation for switching from cute to darkly offensive (and back) at the twitch of an eye. It serves well to wrong-foot her audience. You don’t know if this vaguely dirty setup will lead to an awful punchline or a clever bait-and-switch. The shock is often still the point, but what makes Silverman stand out is how great her writing is, and how multilayered the journey to that shock-or-not payoff. In recent years, Silverman has started focusing more of her energy on making socio-political points with her comedy, but she’s still got the ability to pull a sick gut-punch out of her sleeve. On her Netflix special A Speck Of Dust, she paints a darkly vivid portrait of her sister drunk at a college party, loaded with sinister overtones, before pulling the rug out from under us. 

3. Doug Stanhope on The Fetal Viability Debate

A self-proclaimed anarchist and a self-admitted drunk, Doug Stanhope is a maestro at making you laugh at the most awful, appalling things. He excels at setting up outrageously provocative arguments and using them to make you see things from a different perspective. He doesn’t always get it right and doesn’t always get away with it either—one set at the Edinburgh Fringe ended in a “violent affray” and a “riot” with police called. But when he gets it right, like the pro-choice “heartbreak of an abortion” bit on his recent special The Dying Of A Last Breed, which manages to make a progressive argument in the most provocative manner possible. 

4. Frankie Boyle and the Queen’s Speech

The controversies section of Frankie Boyle’s Wikipedia page is almost as long as the rest of the entry combined, so maybe he’s not the best at getting away with dark jokes. But then the Scotsman makes so very many of them. From sexuality to royal incest, disability to gruesome death, nothing is off the table for Frankie. Some of the earlier stuff—especially the ones about HIV and individuals with disabilities—seems beyond the pale now, but Boyle somehow managed to ignore the outrage and the brickbats and keep going, helped by his obvious sympathies for the working class and the underdogs of British society. There’s a lot of punchlines to choose from, but our vote goes to this Mock The Week one liner about the Queen.

5. Tig Notaro on Kicking Her Baby 

For much of her early career, Tig Notaro was known more for silly absurdist gags—like pushing a stool around on Conan—than for dark punchlines. But then in 2012, she lost her mother, broke up with her girlfriend, survived one life-threatening disease and was diagnosed with breast cancer. Grappling with the fear and terror of that experience—and the years that followed—gave Notaro an endless supply of the grimmest of material to subject to her uniquely absurdist comedic lens, giving us gems like this deliciously deadpan bit that features visual imagery like “tiny little baby head flying across the room.” 

6. Daniel Sloss Fantasises About His Partner’s Death

On a scale of 1-10, how dark is ‘gleefully boasting that your standup special broke up over 50,000 relationships’? That’s how many couples Daniel Sloss claims to have separated, right before he announced his own engagement. The Scotsman, who started off writing jokes for Frankie Boyle, excels at intelligent, self-aware gallows humour: following up the most provocative punchlines with emotional U-turns and “gotcha” deconstructions. A great example is the bit below about catching yourself wondering how much better life would be if your partner died. 

7. Maria Bamford‘s One Night Stands

Maria Bamford excels at a uniquely whimsical brand of dark humour, one that a headline once proclaimed “makes facing nightmares fun.” Combining absurdist character sketches with extreme confessional vulnerability, Bamford—like Notaro—mines fear rather than shock for her black comedy, though her fear is more focused on the fickleness and unreliability of the human mind. So you get the grimmest, most self-exorciating punchlines, like this extended bit from her Netflix special Old Baby about 15 years of motel one-night stands.