Donald Trump was the subject of the Comedy Central Roast back in 2011, holding a forced, plastic smile while being skewered by emcee Seth MacFarlane along with Snoop Dogg, Jeff Ross, Larry King, Gilbert Gottfried, and how can we forget–Mike “The Situation” Sorrentino.
In an awesome Huffington Post oral history of the event, we are given perplexing insight into the motives for Trump’s participation, his insecurities, and his obsession with polling participants of the roast if they thought he should run for President.
After agreeing to do the roast in late 2010, Trump immediately made it very clear of the boundaries comics could not breach.
Trump Tower made it known that two subjects were off-limits: Trump’s past bankruptcies, and any suggestion that he was not as wealthy as he claimed to be.
In August, Aaron Lee, another roast writer, posted a note on the appthat referenced Trump’s prohibition on, “any joke that suggests Trump is not actually as wealthy as he claims to be.” Bankruptcy jokes are the “one thing [Trump’s] super sensitive about,” Ross told Jimmy Kimmel in July.
Rick Austin, who served as producer for the Trump roast, revealed that the network doesn’t typically have the roastee approve of the jokes, but they do get to cite a few things that are off limits. William Shatner, a participant in the 2006 Roast, requested that no jokes be made about his third wife Nerine, who drowned at the couple’s home.
Another mandate: Trump voiced that roasters should address him only as “Mr. Trump,” claims Comedy Central’s senior vice president, Jonas Larsen.
As you know, the roastee gets an opportunity to hit back on the abuse they’ve endured over the hour-and-a-half verbal beatdown. The team of writers hired to provide Trump with rebuttals had a nightmarish time getting ‘Mr. Trump’ to get on board with their comedic direction.
After the writers went through numerous drafts of Trump’s rebuttal, they forwarded a version to him in early March. He responded a week later with his first set of edits, handwritten in black Sharpie.
“I have done this a long time and nobody blacks out punchlines,” said Jesse Joyce, one of the writers. Scrapping punchlines represents “a classic lack of an understanding of how a joke works,” he added.
Trump’s edits were all over the place. He crossed out an entire riff on condoms in the first draft, scribbling “No” in the margin. Elsewhere, he seemed to revel at opportunities to be crass. He complained a line suggesting Lisa Lampanelli should “shut the fuck up” didn’t end with an exclamation point. But in a later revision, he wanted to switch the line to “get off the stage.”
The writers also reveal Trump’s obsession with expressing how wealthy he is in the most trivial of details. They also tirelessly, and ultimately effectively, convinced him to accept jokes about his hair.
The writers eventually convinced Trump to “own” his hair by wrapping follicular self-deprecation into a boast about his wealth. The joke, not in the rebuttal drafts obtained by HuffPost, originally went: “What’s the difference between a wet raccoon and Donald Trump’s hair? A wet raccoon doesn’t have $2 billion.” Trump eventually agreed to use the joke, according to several people involved in the show, so long as the $2 billion was changed to $7 billion. Ross told Kimmel that settling on the amount was like a “business negotiation,” with Trump initially wanting the number to be $10 billion.
Despite all the ammunition the comedy writers provided Trump five years ago, no joke made me laugh harder than just a few days ago.
Hillary: “It’s just awfully good that someone with the temperament of Donald Trump is not in charge of the law in our country.”
Donald: “Because you’d be in jail.”
For more on the inner working of the Donald Trump Comedy Central Roast, head over to Huffington Post.