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We all love things that bring us pain. Perhaps it's the wrong woman, or our local sports team that never wins, or something else.

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"Nipple clamps? Is it nipple clamps?"

But this is an article specifically about what breaks my heart in comedy. The funny things I love that bring nothing but pain.

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"Nipple clamps are funny. Is it nipple clamps?"

No. It's not nipple clamps, it's these:

Seemingly Politically Incorrect Jokes That Are Totally Fine

Let me be clear. Dropping words like "nigger" and "faggot" and "kike" doesn't earn you a place in my heart. Any rabid dog can hate, and any no-talent hack can replace actual jokes with a merely edgy vocabulary. But I do love jokes that aren't afraid of offending. You can fracture and deconstruct stereotypes in a way that dances with hatred without embracing it. For example, there is such a thing as a non-homophobic gay joke. I've always loved this one, and I stand by it as being completely appropriate:

Q: How do you tell if your roommate is gay?
A: His cock tastes like shit.

The joke does not mock gays or gay sex practices. It's a joke about misdirection. The humor comes from the notion that some dude would be blowing his roommate in an earnest attempt to find out if he's gay. Still, I'm sure it's upsetting to the politically correct.

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This is the only pic that comes up in a photo search for both "offended" and "sleepy-time yoga."

My contempt for the PC movement really crystallized in college. I went to school at the height of political correctness. On my first day of school, my RA told us all that the word "girl" was "hate speech." Of course, I didn't have to stay in that dorm. I could have moved out into a fraternity and been surrounded by dudes who wouldn't sweat those details, but I thought frat guys would be too conformist, small-minded, and mean. So, my sophomore year, I moved into a dorm of architects, freaks, and sexually fluid individuals who were very concerned about creating a nurturing environment where no one would call any of them a "fag." Instead of circling kegs and harassing women, they spent a lot of time congregated in pre-hipster circles, spewing their own contempt at people who weren't like them. Over the course of my four years at school, I saw enough to realize that there were good people in the world and hateful bigots too, but trying to figure out who was who based on what words they used (or jokes they told) was probably the least helpful way to go about it.

So when I see a joke that I know would piss off my old RA or those precious sophomores but is actually too clever and open-minded to have ever been told by some thick-necked frat guy, I fall in love. Problem is, however, most of the world falls into one of those two extremes, which means telling jokes like that usually involves a lot of painful explaining.

Mocking Deaths

I have to be careful about this entry, too. I'm not one of those people who say "It's a comic's job to joke about anything!" or "There is no line." There is definitely a line. And I'd say it's only a comic's right to joke about anything he can make funny. Now it goes without saying that the more horrible the thing is, the harder it is to find the humor in it. There are things I'm pretty sure will never be made funny, but if you can figure out how to actually make non-horrible people laugh about baby murder or genocide, then fine, go ahead, do it.

Personally, I like cracking dark jokes about celebrity deaths, and I do it a lot on Twitter, usually costing me two followers for each new one I gain every time I do it. Not all celebs stir me to action, and not all deaths become comic fodder. There has to be something to justify it. It helps if the deceased was garbage. That would be the case with my Joe Paterno tweets.

Most people (outside of Penn State fans, who apparently can forgive anything) didn't mind that one so much.

But when Amy Winehouse died, I wrote an entire obituary for her, devoid of sympathy. It was a reaction to all her fans bemoaning her loss to addiction when so much of what made them her fans in the first place was her defiant embrace of addiction. Turns out it was the only article of mine Cracked has ever rejected, and although some readers agreed with my reason for its existence, many felt it was just far too ghoulish, and, as such, its rejection for the site's readership was probably proper. (Incidentally, that rejection wasn't such a bad thing because it inspired some further reflection on my part, leading me to write a better piece that Cracked did publish). But I stand by the initial obit. When something dark makes me laugh, I have enough faith that it's not because I'm a sociopath, and that leads me to ask questions. And that's how a comedy loser like me has fun.

Or sometimes I find a way to make a joke about death that isn't really meant to be a giant fuck you to the deceased, like when Steve Jobs died:

To me, that was just making fun of Mac fanboys more than Steve Jobs, but yeah, it pissed people off. And that's OK. If you go dark, even if you're well-intentioned, you will take shit along a sliding scale of people's subjective tastes. And not speaking ill of the dead is one of the most ingrained things there is in society, so get ready.

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I don't want to say too much about this, because I've already written two articles about satirists who were crucified by people who missed the point, but I couldn't discuss comedic things I love that bring me pain without mentioning satire. It's true, people hate satire. It's confusing. It upsets them. Wanna know something else? Lots of people who claim to love satire also don't get it. I've had non-satirical works of mine defended many times by people who wrongly called it satire. It works both ways.

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"Satire like nipple clamps? Nipple clamps work both ways!"

In a nutshell, although the definition of satire can be broad, what I'm referring to most are the kinds of satire that adopt the voice of the thing they're criticizing. That's the part that messes people up the most. Stephen Colbert is not an ardent conservative. He adopts that rhetoric to reveal the flaws in its logic. Jonathan Swift cold-heartedly proposed eating the babies of the poor as a way of criticizing indifference to their plight (while ridiculing wrong-headed social programs). But why say the opposite of what you mean, dude? It's just extra work for the reader. And people hate working. Still, the things we work for penetrate our minds most deeply.

I really don't want to mention my name only a paragraph away from Colbert and Swift, but if I had to recount my most painful experience with satire, it would involve a comment fight I had with a gay woman I offended to no end with my piece supporting gay marriage. It was written from the perspective of a small-minded straight man completely clueless about the gay community and indifferent to the need for gay marriage to be legalized. By warning gays against marriage, it was my intent to show why only a fool would oppose it. Yes, many people, straight and gay, got it, but man, was that lesbian pissed. It killed me. It still kills me. Trying to write something helpful and being attacked by the very kind of person you're hoping to help is hard to shake. I still remember her name, which is more than I can say about any random troll who's called me a "retarted fagget."

Greg Giraldo

Greg Giraldo was undeniably brilliant. He was also side-splittingly hilarious, a husband and father, and a drug addict. Greg Giraldo is dead.

Greg Giraldo is my hero (except for those bits at the end).

You probably know Giraldo best from his appearances at Comedy Central roasts, absolutely demolishing the guests and panelists with a visceral mix of highbrow and lowbrow barbs.

You can find his stand-up special online as well, and it's pretty strong, but what made me a Greg Giraldo fan was his work on Colin Quinn's old show Tough Crowd. Every day, he would show up smart and prepared. Giraldo was not a one-trick pony. He had a deep bench of abilities and a wealth of experience to draw upon. His pairing of satirical intellect and sheer funny simply beat the pants off every other guest in every single episode.

Nowhere was that more clear than when Denis Leary came to the show. At that point, Leary was no longer at the height of his popularity as a comic, but was still the big name of the panel and still relying heavily on his schtick of attitude over material. He thought he could just show up and goof on current events, but Giraldo came to play. Clearly both jealous and intimidated, Leary set out to actively step on Giraldo's jokes. He then proceeded from joke-stepping to openly mocking Giraldo for doing well. Basically, Leary was just like any bully you've ever seen. Not only was he picking on someone for all the wrong reasons, he was doing it out of his own insecurity while surrounded by his old buddies Lenny Clarke and Colin Quinn.

Except Greg Giraldo -- a young comic getting sucker punched and surrounded by a heavyweight -- had something that Leary didn't have: brains and balls. He did not back down. He topped him in sheer intellect, he topped him in funny, and when it looked like it might get physical, he did not blink. Here is, literally, with no hyperbole, one of the greatest things I've ever seen:

The "little" guy won. The smarter guy won. The more talented guy won. The braver guy won. This clip is everything that is right with the world. This clip is justice. This clip is what you show your son if you want him to grow up to be a man.

Of course, time rolls on. Denis Leary transitions into an actor, which doesn't require him to make actual jokes or do his comedic homework, and he's still alive and doing great! Giraldo, on the other hand, did not cross over to the next level. I don't know what drugs he was addicted to or why he couldn't quit them. I don't know how hard he did or didn't try. I just remember he OD'd, spent some time in a coma, and died. And we can't blame that on Leary or the business or even the people too stupid to love him as much as I did. There are few people whose respect I wanted more than his and I'll never get it, and we will never see another moment like the one in the video above. A moment that just for a second made life look like a game that could be won if you did all the things they taught you as a child living in a world that was fair.

Come see Gladstone do stand up at NYC's Bareburger on May 22, 2013 and the Gotham Comedy Club on May 28, 2013. Also, be sure to follow Gladstone on Twitter and stay up-to-date on the latest regarding Notes from the Internet Apocalypse. And then there's his website and Tumblr, too.

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