I had been writing ZUG for eleven years, and the idea for a ZUG book had been slowly forming in my mind. The original idea, however, was quite different: I wanted to do a book of "experiments" like The Viagra Prank and The Aphrodisiac Prank -- things that everyone is curious about, but too afraid to try.

"Just stick with a book of pranks," my editor advised me after I pitched him this idea. "Your audience knows you for pranks. Stick with what you're known for."

My editor was right on almost everything he advised me. Soon after, Esquire put out a book with a very similar concept to my original idea, which didn't sell crap.

"Make it 100% new material," my editor also suggested. "Don't reuse anything from the Web site." I fought hard on this, arguing that no established stand-up comedian would do an HBO or Comedy Central special using completely new material. If you're Chris Rock or George Carlin, you refine a new act over a course of many months, testing it out until you only get the best stuff. You pan for comedy gold.

"I have to include some classic ZUG material," I said. "Stuff that I know is funny." I wanted 50/50 classic/new material. My editor wanted 100% new material. We compromised, and the final book is one-third "best of," and two-thirds new material. And some of the "classics," like the Ashton Kutcher prank, have the complete "behind the scenes" story, which I intentionally saved for the book. Also, I ended up writing a lot more than originally predicted, so in essence, there's a book's worth of new material in PRANK THE MONKEY.

This underscored a bigger philosophical debate, which was whether the book was intended for current ZUG readers, or a wider audience. Clearly we had to cater to both, but my editor felt that ZUG readers would be the primary audience, and not to worry about anyone else. I argued that bookstore distribution of PRANK THE MONKEY would expose my writing to more readers, so I should try to appeal to the widest audience.

In the end, we tried to strike a balance. For example, "The Untied Nations," where I pranked the entire United Nations, is full of inside jokes for ZUG readers. Not surprisingly, most of my test readers were cool to this chapter -- except for the diehard ZUG fans, who rated this their favorite part of the book. (For what it's worth, this chapter has the biggest laugh for me personally.)

One final piece of advice from my editor: "Make your first book the best book you can possibly write," he told me over the phone. (I didn't even meet the guy in person until a year into the project.) "Don't save anything for the second book. Unless the first book is great, there won't be a second book." I took this advice to heart, and pulled out every big idea, great story, and classic bit that I had been saving for a "special occasion." So now I have nothing left for a second book, but damn this first one kicks ass.

I had cut a book deal. Now I had to figure out what the hell I was going to write.

Next: Framing It Out!