How To Write Jokes That People Will Laugh At (But You Won't)

Literally the second humor essay I ever wrote was a homophobic, slut-shaming piece of shit.
It was also pretty popular.
I was nineteen, and in college, and had decided to write for the college paper.  I loved George Carlin and Lenny Bruce and all of those groundbreaking comedians, so I decided to work as edgy as I could.  My first essay, “Religiously Handicapped,” was about how I didn’t know what to do in Church, and to this day I’m still weirdly proud of it – it’s not funny, but it mines a vein of comedy that wasn’t too common back then.
I forget what the second essay was about, but it was where I betrayed myself.
In that essay, I remember mocking the men who offered “relief” to college students in the papers – a proto-Craigslist personals, where dudes sought out other dudes to do dudely things upon.  And I mused upon what sorts of reliefs might be offered by dudes to dudes, and made a sketchy comment that was something like, “Ugh, who’d want that kind of relief?  No thanks!”
I got a lot of positive responses, because particularly in the late 1980s, making fun of gay men was still pretty fucking funny to most people.  Especially to sexually-terrified college dudebros.
Thankfully, I had a handful of gay friends.  And they took me aside and told me that the personals were the only way for a lot of gay men to connect in a town like ours that really looked down on homosexual sex, and they had to talk in code like “relief” because most of what they did was borderline illegal, and honestly, Ferrett, that was a pretty dickish joke.
Thing is, I knew all that.  Heck, the reason I knew about those personals is that I was tempted by the idea of loose, anonymous sex myself.  In truth, my reaction to those ads wasn’t revulsion, but a sort of terrified fascination, a desire to know just what sort of things might happen if I went over to a stranger’s apartment and let him have his way with me.
But you know what played better on campus?
Eeeeyew.  That’s what got bigger laughs.
So I made the unfortunate choice to prioritize what I thought people would laugh at over what I personally believed.
This is not an unusual thing, for anyone working in humor.  Anyone who wants to be a comedian or a funny writer doubtlessly does so because they’re a fan, and they’ve listened to every album/watched every standup/seen every funny show they can.  Comedians have memorized other comedians’ routines, because they dissect them, know what makes them tick.
And they remember vividly where people laughed.
So when you’re just starting out, you often are so desperate to please that you drift into autopilot and make a gag that you don’t believe in that’ll go over well.  Fat chicks and sluts get laughs.  Up North, a cheap “Oh, those stupid redneck Southerners!” draws inevitable chuckles, just as I suspect there’s some boilerplate dumb prissy yankees jokes going on down South.
It’s the moral equivalent of making the “What’s with the airline meals?” jokes – you can get laughs because a lot of the audience shares that experience, but is that really what you’re amused by?  And you see that in a lot of the earliest known works of famous comedians – Louie CK’s first special is pretty mundane.  He’s making gags that are kinda funny, because he’s gotten talented enough to make jokes, but they are not yet his jokes.
A good comedian can get laughs with their material.  A great comedian makes jokes that only they could make.
For many, it takes a while to learn that you don’t have to go for the laugh.
Early on, a lot of people are just happy to get a positive reaction.  And it’s only later, when you take that positive reaction for mostly granted, that you start to look at what kind of audience you’re amusing, and wonder what the fuck you’re doing.  And that’s not just whitebread yok-a-blocks like me; ask Dave Chappelle why he doesn’t like touring any more.
And if you’re skilled, eventually you start to find your voice.  I realized that even though everyone else thought fat chicks were a solid target, including my audience, I didn’t have to use them as a punchline because I personally thought BBW women were beautiful.  (Hence the reason I put an attractive pudgy woman front-and-center in my book Flex.)  I realized that it’d be a lot more interesting if instead of condemning anonymous gay sex, I actually faced it honestly. (And then, growing even wiser, realizing that I had no personal experience with the topic and maybe I should discuss something I had actually done.)
I started to set my own boundaries on what I thought was funny – and I’m no Louie CK, but I have gotten a mild audience that often laughs at my weird-ass jokes.  And when you do that, you don’t have to have some sort of come-to-Jesus moment where you beg forgiveness from the audience – you just stop making certain kinds of jokes (and wince a little when That Dude tells you that was the funniest shit, man) and quietly move into new territories, evolving.
The reason I say this is because right now, the new Daily Show host Trevor Noah is taking a lot of beatings for some pretty dumb-ass jokes he did on Twitter, which have been exhumed and are now being trotted about as proof that he’s unfit for the job.  And Trevor hammers the “Jew” and “fat chicks” realm embarrassingly well, here.  (Though we must also remember that Jon Stewart made some pretty anti-women jokes in early seasons of The Daily Show – almost certainly stemming from that automatic reflex of “They’ll get a laugh.”)
So what’s Trevor actually think these days?  I have no idea, actually.  I’d never heard of him before the announcement, so I can’t tell you he’s evolved.  (The fact that some of these gags are from 2012 doesn’t fill me with extreme hope.)  He’s Schrodinger’s host – maybe he’s evolved beyond these crutches of guaranteed laugh-getters, maybe they’re part of his voice.  (Because sometimes, you find your actual voice and it’s repellent – something that happens in comedy a lot, too.)
What I am saying is in response to this:

32. Most of us don’t say things like this on twitter because we don’t fundamentally believe them, or aren’t stupid enough to admit it.
— Morgan Leigh Davies (@MLDavies) March 31, 2015

And I think there’s a third option for why someone posted dumb shit like this beyond “We fundamentally believe in the trope” or “Are stupid enough to admit it” – it’s “We knew it’d get a laugh, and thought the laugh was harmless.”
But laughter isn’t harmless.  Laughter, directed in the wrong direction, can cripple the weak, rub their face in their own impotence, destroy their sense of self-esteem.  That’s why you try to punch up with your jokes – making gags at the expense of people who, frankly, have enough confidence and overweening sense of self that it’s probably a public service to take the piss out of them.
Again, I can’t speak to Trevor myself.  But I’ve watched a lot of comedians grow, and by the time they came to my attention they first made some ugly jokes they later dispensed with.  And note that was “by the time they came to my attention,” which is to say after enough years working in the field that they got that television appearance they’d hoped for (or that YouTube video that went viral enough).  They probably made lots more bad jokes.
I’m not saying everyone does this, of course.  Some are lucky enough to refuse to make jokes just for the sake of laughs.  They’re usually more compelling voices from the get-go.  But a lot of us have to have that moment – several moments – where we go, “Okay, wow, people laughed, but I didn’t.  Is that the sort of person I want to be?”
If you’re lucky, you become someone else entirely as part of the process.  Someone stronger, more thoughtful, and more moral.
You know.  Like the sort of dude Jon Stewart became.