xmlns:og="http://ogp.me/ns#" xmlns:fb="http://www.facebook.com/2008/fbml

How to Write a Joke


Most good jokes are tiny stories with surprise endings and adverse consequence. They contain two parts; the set-up and the punch-line. The set-up takes your mind down a path of predictable outcome. The punch-line changes the outcome to something unexpected, while at the same time detrimental. In other words, a little trick was played on your mind, revealing that someone got hurt.

I wrote the above paragraph for the introduction to my first joke book, The Vile File – Jokes Too Sick for the Stage (1999; Trailer House Press). Then I went on to explain the importance of adverse consequence, and why many – especially the comedy jaded – are especially fond of dark comedy. I put it this way, “There is a child-like mischievous delight in thinking that something is so wrong to laugh at – I can’t believe I thought or heard or said it – that strikes hard at the funny bone.”

Because I’m a one-liner comic with some decent bits in my act, I sometimes get asked for advice on writing one-liners. Besides the obvious goal of “brevity being the soul of wit” and the essential formula of surprise plus consequence, my advice is simple. Consume as much comedy as you can. If you have talent, the fundamentals will be absorbed.

I have read several “how to” books on comedy writing, but learned little from them. Mostly they reinforced what I instinctively knew. I’m guessing, I am not alone. The way I figured out how to write jokes was by studying comedy. And by “studying,” I mean enjoying those who best create and perform it.

Keith Richards is one of the most influential guitar players in the history of rock ‘n’ roll. In his terrific autobiography, Life (which I wrote about in a post), Richards credits his song writing success to his love of Chicago Blues and spent a lifetime listening to the recording artists he admired. Stephen King, in his terrific book On Writing says, “If you want to be a writer, you must do two things above all others: read a lot (emphasis mine) and write a lot. There’s no way around these two things that I’m aware of, no shortcut.” I have to believe that the same rule applies to joke writing. 

As I began my joke writing journey, my three biggest influences were Rodney Dangerfield, Steven Wright and Emo Phillips. If it’s great jokes you want to write, I suggest you study these masters. I highly recommend: Rodney Dangerfield’s autobiography (which is filled with jokes), Not Easy Being Me: A Lifetime of No Respect but Lots of Drugs and Sex, and his classic album, No Respect; Steven Wright’s classic CD/DVD I Have a Pony; and anything and everything by my personal hero, Emo Phillips (he also has a terrific recipe for cole slaw, which I also recommend).

I also humbly suggest you read my new joke book, More From the Vile File (published by Stand Up! Books). Certainly, there are lots of joke books on the market, but I’d like to believe mine is special. The typical joke book is a collection of old street jokes, the “author” collected and edited, but didn’t write. No doubt, most of these joke books contain some funny stuff, but inevitably they contain a whole lot of filler (terrible) jokes too. Plus most of the jokes, good and bad, tend to be ridiculously long and horribly contrived. “A hooker and a Martian walk into a bar….” I’ll admit that my book contains some “filler” too, but at least you didn’t waste much time in reading one of my groaners.

There are a few good joke books which are collections of the “best of” comedy bits and one-liners from stand-up comedians. I suggest you read those too. I contributed to one such publication, The Complete Idiot’s Guide to Jokes (Alpha Books; 2006; edited by Larry Getlen). But to get into the mind of the comedy writer, I believe it’s essential to immerse yourself in a singular “comedy voice.”

Why is one voice so important? I propose a test to my theory. Remember back to when you first heard Mitch Hedberg perform comedy? Did you not find yourself thinking of Mitch Hedberg-esque jokes the rest of the day… or week… or your entire open mic comedy career? If you can’t answer this question, and aren’t familiar with the brilliant comedy of the late great Mitch Hedberg, add him to my “highly recommend list” and buy Strategic Grill Locations first.

My best joke writing burst of creativity occurred 20 years ago, on my drive home from a Steven Wright concert. Fully formed one-liners spilled out of my head, including one of my career best bits, which I opened with the first time I did The Bob and Tom Show. That joke helped make that appearance a big success, and was included on Bob and Tom Show CD You Guys Rock.  “I had job once selling security alarms door-to-door. I was really good at it. If there was nobody home I’d leave a brochure on the kitchen table.” I wrote that entirely thanks to the inspiration of Steven Wright. My subconscious was trying to channel his genius. It remains one of my goals to this day.

Twenty-five years in the writing, my new book is more than a sequel, it’s also a compilation of the best jokes from my first book, and the best bits from my live comedy CD. Chapter One contains 150 jokes and is titled, Best of The Vile File – Jokes Too Sick for the Stage. Chapter Two contains 75 “tried and true” jokes and is titled, Best Sick Jokes from Quickies. Chapter Three contains 275 jokes.

For a limited time, and for this promotion campaign, I am offering it as an e-book from Kindle for the low price of $2.99. It is also priced inexpensively from Google Play, $3.84. Speaking of Google Play, I’d like to think my little joke book would be a nifty thing to have on your smart phone. You know, like when you’re bored while waiting at a bus stop or for an open stage to begin. You have an app for that!

Why am I targeting my book to comedy writers and aspiring comedy writers? The obvious reason is that I hope to sell a few books, which should (hopefully) get me some (positive) reviews, which would in theory, boost my Amazon/Kindle/NOOK/iBook/Google book’s rankings, which should further help generate sales. Naturally, I would like to profit from my work, but honestly, at this stage of my career, it isn’t all about the money. I don’t know how much longer I can stay alive in this crazy business (especially with my unique style of doing only one-liners) and have begun to think about my legacy. It is my great hope that when all is said and done, I might contribute a little something to the art of comedy which I have spent a lifetime pursuing. Of course, I realize that it’s unlikely you will read my book, cover to cover, in one sitting, laughing until your belly hurts, like you might hope to do at a comedy club. But I would like to believe that some of the jokes in More From The Vile File – and the style in which I write and perform them – will stand the test of time.

More From The Vile File: 500 Sick Jokes is available in paperback from my website using PayPal (autographed copy); and from Amazon. The e-book is available from Kindle, NOOK,  iBook & Google PlayI will be happy to send free copies for review or promotional purposes. If you’re an accomplished professional in the field of comedy, or a reviewer, reporter, blogger or podcaster (or anybody who promises an honest review on my Amazon page), send me a request and I will send you a copy (digital or paper back). You can also read free samples at both the Kindle Store and Google Play. The best sample is at Google Books.

If you like writing jokes, I hope this helps.


A great joke writer. – Tom Griswold on The Bob and Tom Show, May 16, 2013


That’s a funny book. – Colin Quinn, outside the Comedy Cellar in New York City, commenting on The Vile File, Jokes too Sick for the Stage (see blog post), the summer of 2000


Dwight York, as inventive as he is suggestive, is what Steven Wright would be if Wright had Robert Schimmel’s blue streak, and that’s a  compliment to all three master comics.Laughspin review of Quickies (2009; Stand Up! Records)


York delivers a rapid paced series of very funny and original one liners, most of which you will want to repeat to your friends and a few of which you can share at the office. There may be a couple of groaners and moaners on this CD but even those jokes are quite good.The Serious Comedy Site review of Quickies


This joke book is a lot of fun.The Serious Comedy Site review of More From The Vile File: 500 Sick Jokes

Leave a Reply

Tour Dates
  • Events are coming soon, stay tuned!