A former head writer for the Oscars shares what it's really like to write jokes for the most prestigious awards show

Vilanch says the writers are aware that certain celebrities are off limits to joke about, either because the situation is too embarrassing for them, the joke would be too cruel, they will be in the audience.

"You have to be careful to not cross the weird line," he told Sacks.

Vilanch remembers a joke from the 2003 Oscars in which host Steve Martin would have said, "I have good news and bad news. The bad news is that my fly was open throughout the monologue. The good news is that the camera puts on ten pounds."

Vilanch, his team, and even the network censor thought the joke was hilarious, but Martin didn't feel comfortable delivering it at such a classy event.

Vilanch understood Martin's dilemma though, because a joke at the Oscars will stick with you throughout your career.

"The choice you have to make is, do I, as a comedian, want to be remembered for this joke or not?" he told Sacks.

Vilanch says backstage is frantic and chaotic because the writers are coming up with jokes on the spot in response to unpredictable events.

"It makes the fall of Saigon look tame," he explained in the book. "It's all happening so, so quickly."

For example, at the 2003 Oscars, Michael Moore won Best Documentary Feature and spoke against the second Gulf War during his acceptance speech. When he finished, the show cut to a commercial and the writing team started brainstorming how they could reference his speech in host Steve Martin's next line.

By the time the commercial break ended and Martin walked back onstage, they had rewritten his opening line: "It's so sweet backstage, you should have seen it. The Teamsters are helping Michael Moore into the trunk of his limo."

While both the live and at-home audiences are important to please, Vilanch says the writers tend to cater the jokes for the live audience. "You're playing to the auditorium because they're the ones who are giving the immediate reaction that the home audience will hear," he explains.

Illiciting a positive reaction from the live crowd becomes more difficult as the night goes on for up to three or four hours and many of the members becomes disappointed they didn't win an award.

"Their high hopes are gone," Vilanch told Sacks. "For every winner, there are at least four or five who won't win. It gets chilly."

Besides, all of the stars have spent long days getting ready, taking pictures, and doing countless interviews. By the end of the night, they don't pay as much attention and want to move on to the after parties, he explained.

Some audience members even leave early to relieve their babysitters or because their category has already passed or even because they're bored. Their empty seats are promptly filled with "seat fillers," or various extras, like secretaries from Paramount, who sometimes aren't in the mood to laugh.

While writing jokes for the host is their main duty, the writers also need to come up with relevant jokes for the celebrities who present each award.

It's tricky, Vilanch says, because each celebrity comes with a posse of assistants advising them to "not say this" or "don't say that." Some celebrities even come with their own writers. But that doesn't bother Vilanch too much.

What does bother hima bit, however, are celebrities who are so nervous about telling a joke that might ruffle some feathers that they start to ask everyone and their mother for opinions on the joke. The joke gets so edited down that it's not really funny anymore.

"You can't be funny by saying, 'I'm not going to get anybody into trouble,'" Vilanch told Sacks. "You know, that's the risk you run."