This story appears in the July/August 2016 issue of Playboy. Subscribe

Risky comedy is edging closer to extinction. Unfortunately, this shift isn’t happening because our culture has become so progressive that the proverbial line is nearly impossible to cross. Quite the opposite: The level of tolerance for daring humor has retreated. Collective cries of the offended are amplified by retweets, online petitions and college op-eds from the vice chairperson of the Students for Nondiscriminatory Language Committee. ¶ How the hell did this happen? There’s no clear perpetrator, no outspoken right-wing televangelist, no Tipper Gore, no McCarthy-like politician foaming at the mouth over every tits, ass and dick joke. No, in this age of pervasive political correctness and cries of “micro-aggressions,” we’re doing this to ourselves. ¶ Playboy sought out some of today’s funniest comedians and asked them to tell us about the most fearless jokes they’ve heard and the comics who crafted them. What we found are jokes that take on the most salient topics of our time—terrorism, abortion and race, to name a few—and are absolutely hilarious.

LEWIS BLACK: Paul Krassner on the Assassination of President John F. Kennedy

In 1967, William Manchester published The Death of a President, a historical account of the JFK assassination. But Jackie Kennedy and Robert Kennedy had insisted that parts of the manuscript be removed. Amid that censorship controversy, satirist Paul Krassner provided the “missing pieces” in The Realist, his underground paper.

I would get The Realist in the mail. I don’t know how my parents let me do this, but it would show up, black and white, 20 pages, and one issue had a supposed excerpt from Manchester’s book.

I’m of that generation for whom Kennedy’s assassination was massive. The game board changed. We were playing Monopoly, and now we’re playing Psychosis.

Up to that point, the big thing in terms of over-the-top comedy was Lenny Bruce saying Jackie Kennedy was scrambling to get out of the car. But Krassner wrote in The Realist that Jackie was on Air Force One with her family and Lyndon Johnson, flying back with the casket with President Kennedy’s body in it. And she goes to the back and notices that Johnson is hovering over the casket. As she approaches, she slowly realizes—this is a summary—that Johnson is fucking the bullet hole in Kennedy’s neck.

It was like somebody gave me a drug. It literally made my head explode. I yelped, and then I laughed, and then it was…disorienting. It was beyond my imagination. It was beyond my imagination’s imagination that you could even do that. Or say that. And back then there were still taboos. Back then, “going too far” was a real thing. It wasn’t just a question of “too soon.”

That joke changed the way I looked at the world. You have to realize, they were pulling the rug out from under Kennedy. It was the first shot across the bow of all of this stuff that would come out later: “Our leaders are not who they seem to be.”

KELLY CARLIN: George Carlin on Abortion

When I was a kid, I didn’t really understand what my father was doing in a larger context. It didn’t dawn on me. He was my dad. But in my 30s I started to appreciate the power and the true boldness of his comedy. In his 1996 HBO special, he comes out and says something like “Why is it that people who are against abortion are the people you wouldn’t want to fuck in the first place?”

On the surface, it can seem like an antifeminist statement, because he’s objectifying these women who are against abortion. But he’s making this really subtle point about abortion at the same time. And it’s really funny. You can’t help—if you have a certain political proclivity—but laugh from the shock of it and from the truth of it.

When you put something like that out into the world, the risk is that it’s no longer yours. You can’t control how it lands on everybody; everyone has a prism they’re going to receive it through. That’s what’s interesting about my dad’s audience. Not only did he have everyone from nine- to 90-year-olds, but he also had radical lefties and libertarians—and conservatives. Telling that kind of joke—it’s a huge risk.

Jay Mohr on Chris Rock(pictured): “He explains to hundreds of black people what he hates about them. It’s absolutely astoundingly ballsy.”

JAY MOHR: Chris Rock on Race

Chris Rock. Checkmate, Chris Rock. Chris Rock stood in front of a black audience while filming a special. He said, “I love black people; I hate niggers.” Like I said, this was in front of a black audience. They’re all laughing, but you know he’s a comedian, so there’s an explanation to come. So you’re just sitting there thinking, Um, what is happening?

Look, everybody wants to say Lenny Bruce was this pioneer. Lenny Bruce was whacked out on speed, reading his own court transcripts onstage until people left. I could do that if I did speed—because I wouldn’t care about anything but more speed.

But to stand in front of a black audience and tell them what’s wrong with your entire race, citing specifics—checkmate. No matter who else says what in this article, no matter what you think after finishing this piece, just circle back to Chris Rock and see if it’s ballsier than what he did.

It wasn’t like he did the bit at a nightclub. It was a filmed special! There are signs outside saying, “If you enter the premises, you are agreeing to be filmed for HBO.” And he just explains to hundreds of black people what he hates about them. It’s astoundingly ballsy. It’s other level. George Carlin probably went, “Wow!”

If you’re a comedian and you’re not doing something ballsy, go do something else, man. Nobody buys a comedy ticket to hear about how wacky the airlines are.

JB SMOOVE: Richard Pryor on Freebasing

In 1980, after freebasing cocaine, Richard Pryor doused himself in 151-proof rum, set himself on fire and ran through the streets ablaze. He was rushed to the hospital with burns covering half his body and later revealed it was a suicide attempt—something he describes in his 1982 special, Richard Pryor: Live on the Sunset Strip.

Comics are the only ones who can take pain and make it into something interesting to hear. Richard Pryor, to me, was the one who would go into that barrel and express himself so vividly onstage, especially after his tragic incident. Who knows how that changed his life? I was a huge fan, and to watch him do that bit onstage—wow!

To me it shows the level of commitment Pryor had. His level of honesty—I don’t think anyone has come along after that to top what he does onstage. What he does is daring. There’s a sacrifice he makes.

You have to be willing to give part of your life away. Comics don’t worry about people in the audience. They worry about people they have to be around after they leave that stage—the people trying to help them, the people in a relationship with them. The audience doesn’t know the extent of Pryor’s drug use; maybe they think he’s making it up. They don’t know his personal life. They haven’t been in bed with him. They haven’t raised him. They haven’t done anything with him other than watch him on TV and on stage. But someone in his life didn’t know all those details yet, so that’s a whole different thing to give up.

And you have to realize, he almost died. He almost left this earth. Yet he put a take on it that was funny while still acknowledging the extent of what he’d gone through. I’m not just laughing at the bit, I’m thinking, Damn, this is crazy! It’s intriguing, it’s funny as hell, and it’s honest. It’s a powerful moment in comedy.

JB Smoove on Richard Pryor (pictured) Live on Sunset Strip: “I’m not just laughing at the bit, I’m thinking, Damn this is crazy! It’s intriguing, it’s funny as hell, and it’s honest. It’s a powerful moment in comedy.”

ANDY KINDLER: Bill Hicks on Killing President Ronald Reagan

Bill Hicks had a bit about John Hinckley Jr.—the guy who tried to kill Reagan—and how Hinckley’s whole thing was that he wanted to kill the president because of Jodie Foster. Hicks says something like “I can’t understand why it was because of Jodie Foster. I could understand if it was Phoebe Cates.” Then Hicks does a whole thing where he’s running around the White House, killing everybody in the name of Phoebe Cates.

I wouldn’t do that joke. There are certain things I have a Jewish fear of, like you’re never supposed to joke about killing the president. But what’s so perfect is that Hicks would do things I would never do, which means it was probably even more important that he did it. The joke ends with him in the electric chair, sniffing his finger, kind of as a Phoebe Cates memory.

It would never occur to me to go, “Jodie Foster? That’s a horrible choice…but I could see Phoebe Cates!” Remember that scene where Phoebe Cates comes out of the water in Fast Times at Ridgemont High? To me, Hicks picks the exact person you would choose in that scenario.

Hicks obviously hates everything the Reagans represent. Within the context of this fantasy, I’m sure he took pleasure acting it out. I think he says something like “Get back here, Nancy Reagan! Get your skinny ass back here!” while he pretend-runs through the White House, spraying bullets.

I met Hicks in the winter of 1988 on a tour in Michigan. It was right after he got sober. I had started comedy in 1984, and I was actually frightened at how amazing his act was. He was the first comic I saw really be angry. I think he was outraged by the politics of the country. Outraged. He had such strong opinions about how fucked-up things were. So his joke is basically saying, “These people are in many ways criminals, so don’t walk around canonizing them or making them larger than life.” But he’s also making a solid point that if you’re a crazed psychopath, you should have higher standards.

Natasha Leggero on Joan Rivers (pictured): “Joan’s own manager took her aside and said she shouldn’t tell those types of jokes. Back then, being a woman who talked about things like abortion and sex was just not done.”

NATASHA LEGGERO: Joan Rivers on Abortion

Comedy is all about perspective and time period. You watch Lenny Bruce’s act now, and you don’t understand how it got him arrested. Things have changed so much. But when you look at context, it’s Joan Rivers talking about abortion on television. She couldn’t even call it abortion! She had to call it an appendectomy. She had a joke about a woman who had 14 appendectomies, and Joan’s own manager took her aside and said she shouldn’t tell those types of jokes. In her documentary she remembers how Jack Lemmon left her show and was like, “That’s disgusting. Women shouldn’t talk like that.”

Today, if something’s not politically correct, or if it’s bad, it doesn’t matter if it comes from a man or a woman. But back then, being a woman who talked about things like abortion and sex was just not done. Joan Rivers is definitely the first person I know of who did.

The best comics have always gone against the norm. Men at that time were probably afraid of women talking like that. But abortion is something a lot of women can relate to. They have the potential to have, they have had or they’re scared they’re going to have an abortion. It’s part of being a woman. Of course females will joke about that.

Comedians go through life saying the things other people are afraid to say, so obviously they’re going to go into the territory of taboo subjects. Sure, you can go around being PC, making sure you don’t offend anyone. But the kind of comics I like, and the kind of comedic minds I’m drawn to, are the people who say what everyone is thinking. And they’re able to frame ideas in a way that’s not only enlightening and intelligent but also hilarious.

JIM NORTON: Wanda Sykes on Rush Limbaugh and Terrorism

The most unafraid joke I can think of was told by Wanda Sykes when she hosted the 2009 White House Correspondents’ Dinner.

She did a bit about Rush Limbaugh being the 20th hijacker: “He just wants the country to fail. To me, that’s treason. He’s not saying anything different than what Osama bin Laden is saying. You know, you might want to look into this. I think maybe Rush Limbaugh was the 20th hijacker, but he was just so strung out on OxyContin he missed his flight.”

I thought that was so stunning because she did a 9/11 joke in front of the president and the entire U.S. government. She risked absolutely losing everyone by doing that.

I don’t care what side of the fence you’re on politically, who she voted for, whatever. The fact that she did a 20th-hijacker joke—I would never have the balls to do that as a comic. And it was a funny joke.

Now again, it was a White House Correspondents’ Dinner. You really can’t do a higher-profile gig than that or a more prestigious one as a comedian. She was risking a tremendous amount. In this day and age, that kind of risk could hurt your career. I’m always amazed when people are willing to do jokes like that. I’ve heard meaner jokes. I’ve heard dirtier jokes. But as far as overall risk, that’s the one I admire the most.

ARTIE LANGE: Mitch Hedberg on Heroin

Mitch Hedberg had a joke that could have led to some very serious personal consequences.

Mitch died of a heroin and cocaine overdose 11 years ago. Really a tragic end. But he had some of the most amazing, edgiest jokes ever. He told this joke on the radio—and I felt like he sort of looked at me, because he knew I had the same issue—and I could see him in his head going, Should I say this? Because it was clearly true. The joke was “You know what I love the most about my Federal Express deliveryman? He’s a drug dealer and he doesn’t even know it.”

Think about that. Mitch was known for having drug issues. He’d been busted before, and he’d clearly gotten his fix delivered by his FedEx guy. If that joke spawned an investigation of any sort, he’d go to jail.

But you know, that’s who comedians are. That’s an insight into the psyche of a comic. “You know what, it’s a great joke. It’s going to get a laugh. I want to be known for doing great jokes. Even if I’m going to prison, I’m going to say the joke.” That’s what a lot of us have.

DAVE ATTELL: Sam Kinison on Jesus

As a comic, Sam Kinison is totally underrated and one of the guys you wished you were when you watched him onstage. He was that good. Pure energy, rage—it all syncs together so well.

Take his whole Jesus bit: “Jesus is the only guy who came back from the dead and didn’t scare the fuck out of everybody.” If you look at the full-tilt run, it’s great joke after great joke. I’ve heard so many versions of it, but the pure, true first one on Jesus was Sam.

I know he did a bit of it on Saturday Night Live and on his first HBO special. It was basically, “No one knew what Jesus’s last words were, but I think it was something like this”—and he begins hammering his hands into the floor. He’s doing this on television. And he did the whole thing of Jesus saying, “When am I coming back? Tell ’em I’ll be there as soon as I can play the pianoooo again!” He has all these great jokes. It was something of Sam’s that was his brand, unique to him. And the fact that he was a preacher makes it valid.

Today everyone is so PC about religion. You’re allowed to talk about certain things but not others. Sam Kinison was definitely the guy who took it as far as you can go, and every little piece of the Jesus bit is hilarious. He runs with it. You can’t not laugh. It’s great. It’s irreverent.

KEVIN POLLAK: Zach Galifianakis on Racism

The most fearless joke I’ve ever heard is the famous Zach Galifianakis bit. It’s about how much he hates the word nigger. He hates every part of it, any use of it, any context it can be used in. He sets it up by saying he’s very, very sensitive to it. He says, “Like, the other day, I heard someone say the word sandnigger. And it really, really disturbed me. It got me in my heart. It hurt to hear it. And it wasn’t even in the correct context. It wasn’t like the guy said, ‘Hey! Get off the sand, nigger. Don’t you know volleyball is a white man’s sport?’”

Doing that joke in front of a mixed audience, that’s the most fearless I’ve ever seen. It was so beautifully designed that it’s pure comedy. And it completely and utterly defends, and gives an example of, why there’s no place for censorship or political correctness for a stand-up comedian. I mean, you might be offensive to people, but you’re not being racist, because it’s a beautifully crafted and designed joke, and it’s making no comment about a people in any way, shape or form.

I saw him do it live at Radio City Music Hall. He did it in front of so many people—and just leveled the place. When it’s funny, all bets are off. No rules apply.

Todd Glass on Louis C.K. (pictured): “Louis’s joke calls them out on that. It says, ‘You’re not being honest with why you don’t support gay marriage.”

TODD GLASS: Louis C.K. on Gay Marriage

Comedy is a powerful way to get people to change. When people already like you and you say something they don’t agree with, if you do it comedically, you can change their beliefs. That’s why comedy is so powerful. When you hear “It’s just comedy,” it’s usually said by a shitty comic. It’s not just comedy.

In his bit on gay marriage, Louis C.K. goes, “People say, ‘How am I supposed to explain to my child that two men are getting married?’ I don’t know. It’s your shitty kid, you fucking tell him.… Two guys are in love, but they can’t get married because you don’t want to talk to your ugly child for fucking five minutes?”

I call it vulgar poetry. In one clean sweep, it’s like, Really? Is this why we’re preventing people, two consenting adults, from doing a natural thing? Please don’t tell me that’s why we’re preventing two people from showing their love for one another, because you’re afraid you can’t explain it to your children. Louis’s joke calls them on that. It says, “You’re not being honest with why you don’t support gay marriage. You’re just looking and searching for something.”

You know, you can’t get caught in the truth. And the truth is that most people don’t like anything about the world of being gay because it grosses them out. And if they just said that, you’d be like, “Thank you for being honest. Now we can discuss.”

But when you try to hide behind “I don’t know what to tell my children.…” Of course you don’t know what to tell your children! You don’t even know what to tell yourself. And Louis’s joke says it in one clean swoop.

Whitney Cummings on Greg Giraldo (pictured): “The rule we have for these roasts is that it has to be funnier than it is offensive. So if you’re going to make a race joke, it better be an A-plus race joke.

WHITNEY CUMMINGS: Greg Giraldo and Crossing Boundaries

What’s gutsy in Texas might not be in New York. I worked for a long time on the Comedy Central Roasts, where there are no boundaries. So if someone is able to find a line there and cross it, it’s like, wow.

Greg Giraldo always had jokes at those roasts that were fearless not only in what he said but how he said it. He would always go up first, before the audience had anything to drink. It’s five o’clock, they’re settling in, not focused, taking selfies, they haven’t heard any jokes yet. The first comic always gets a lot of cringes and jeers, and Giraldo would kind of break them open. That’s what he did. When they would jeer, he’d go, “Really? We’re at a roast and you’re going to jeer me? Okay, fuck you guys.”

One of his jokes I love is about Ice T. He said, “Ice T, you’re so old, the first thing you bought with your record-deal money was your freedom.” And then he followed it up with “On your first album, the N word was Negro.” It’s like the two biggest taboos, a slavery joke and an old-person joke, all wrapped into one. He just knocked it out so hard. It was super cool to watch.

You never saw a twitch in his eye if something didn’t go the way he wanted it to. And not only did he always have the most daring jokes, but he’d also berate the audience if they didn’t give him the appropriate response.

The purpose comedians serve in society is to find the line and then cross it. It’s our job to constantly poke people to see what offends them and what their boundaries, limits, hypocrisies are. What offends us says a lot about who we are. And people love being offended, because it gives them the opportunity to be sanctimonious, to be above something and feel better about themselves. They get a hit of dopamine when they say they’re offended, and they take time out of their day to do it on Twitter or Instagram. Being offended becomes a large part of our neurological reward system.

The rule we have for the roasts is that it has to be funnier than it is offensive. So if you’re going to make a race joke, it had better be an A-plus race joke.

JEFF ROSS: Dave Attell on Terrorism

It was right after the first World Trade Center bombing at the base of the tower in 1993. It was the first act of terrorism I was really aware of. It was tragic, and New York was on high alert. No one knew what domestic terrorism was all about back then.

As a comedian I didn’t know how to handle something like that. But I went to the Comedy Cellar, and I watched Dave Attell go on. By then he already had the beard and everything. He went up and said, “Okay, maybe now they’ll start taking me seriously.” He basically took credit for the first World Trade Center bombing. The place just erupted with a guttural laugh of “I can’t believe he said that. I can’t believe I’m laughing at that. And I can’t believe we still don’t really know what happened.” That was probably the first time I remember a comic, a contemporary, just going for it.

And then we roasted Hugh Hefner in 2001. I mean, this was three weeks after the Twin Towers came down. I remember writing a letter to Hef, the Friars Club and Comedy Central, saying if we didn’t go on with the show, the terrorists win. That was before it was such a clichéd statement. It was obviously a profound moment in our history. Even people Hef’s age, even my manager at the time, Bernie Brillstein, who was in his 70s, were scared. No one knew what was happening.

To be honest, New York still smelled like death. It still smelled like smoldering remains of buildings and everything. It was a sad time, but we felt an obligation to go on with the roast.

Then Gilbert Gottfried went up and basically changed the way everyone in that room thought about comedy.

Gilbert Gottfried on his 9/11 joke: “I was up there for what felt like—I mean, if you said I was up there for 200 years after I said that joke to when I said the next one, I would have believed it.”

GILBERT GOTTFRIED: Gilbert Gottfried on Terrorism

It was a few days after September 11, and there was talk about canceling the roast altogether. A lot of people who were going to be there were afraid to fly. To make matters worse, the roast was in New York. But they decided to have the roast anyway. All over the country, people were in a daze. But in New York, forget it. So there was tension in the room, to say the very least. I figured I wanted to be the first one to make a bad-taste September 11 joke. The first one was sort of mild. “Tonight I’ll be using my Muslim name, Hasn bin Laid.” And then I talked a little more, a couple more jokes. And then I said, “I have to leave early tonight; I have to catch a flight to L.A. I couldn’t get a direct flight; we have to make a stop at the Empire State Building.”

That got the crowd booing and hissing and gasping—every bad reaction you could possibly get. You could hear chairs moving around. One guy yelled, “Too soon!” At that point, I thought maybe he meant I didn’t take a long enough pause between the setup and the punch line. I was up there for what felt like—I mean, if you said I was there for 200 years after I said that joke to when I said the next one, I would believe it.

Then I went into the aristocrats. It’s a vaudeville-era joke that opens with the same premise each time: A father walks into a talent agent’s office to pitch his family’s act. Every comedian has their own variation. Mine involves the father fucking the wife, who’s jerking off the son, who’s going down on his sister, who’s sticking her finger in the family dog’s asshole.

That joke caused a whole turnaround. The audience was laughing hysterically, what sounded like coughing up blood. Howling and cheering. It seemed to turn into a party atmosphere.

People wrote about it, saying it was like the first time they breathed. Some said it was like the joke at that point was a healing process. One person compared it to performing a mass tracheotomy. For me, it struck me that terrorist jokes were bad taste; incest and bestiality, good taste.

PENN JILLETTE: Gilbert Gottfried and a Private Conversation

The importance of obscenity and disgust in the wake of tragedy is really important to me. I did a whole movie about it, a 90-minute essay about Gilbert telling the aristocrats joke after 9/11. But I’m not leading with a story about a publicly funny thing.

Gilbert and I are both mama’s boys. We were both extremely close to our mothers. When my mom died, it was devastating. Then about a year and a half later, Gilbert’s mom died. As stricken as I was about the death of my mom, Gilbert was more stricken about the death of his. I talked to Gilbert on the phone and went to New York City to see him. And what happened that evening—I’ve never spoken about this publicly—I can’t explain.

Gilbert and I met for supper at Café Un Deux Trois, a French restaurant. We went to a back table. This was within a week of his mom’s death, one-on-one with a friend who’d also lost his mom. You’d expect Gilbert to maybe tell stories about his mom, maybe get a bit philosophical. But what we did was sit across from each other and just vomit up the most offensive jokes we could think of. Now, when you talk about Gilbert Gottfried, it’s hard to even imagine the level he would go to. We went to every taboo in society. It’s not an exaggeration to say that if that conversation had been recorded and disseminated with our names on it, it would be the end of both our careers.

I’m talking about sexist, racist, any sort of distasteful, horrible feeling. We sat back there for probably three hours. And the jokes weren’t punctuation; it wasn’t that we would say, “Oh, and by the way.…” It was talking about raping his dead mother. It was anything you could imagine that was taboo. It was just this gigantic, raging fuck-you to life. It was black vomit of hate spewing out of us, punctuated with insane, mirthless laughter. It was one of the most extraordinary experiences of my life.

Although I was in the middle of it, neither Gilbert nor I instigated it. Neither Gilbert nor I were part of it. Neither of us knew what was going on. Yet we were the only ones there. It was the most visceral, personal interaction with comedy I’ve ever had. It wasn’t comedy used in the way I’d seen it used before. It wasn’t “We went to the wake and we were telling jokes to stop from crying.” That wasn’t it at all. It was not a celebration of our mothers’ lives. It was pure hatred for everything unpleasant in the world.

I’ve thought about that evening many times since. It was our way of throwing a tantrum, destroying a hotel room. It was our way of grabbing a gun and running amok in public. It strikes me as a wonderfully safe, kind, cathartic way to do it. And it remains that way—as long as I never repeat the jokes.