Enlightening background on Trump's attitude toward comedy and apparent inability to understand what's funny:
https://www.huffingtonpost.com/entry/the-inside-story-of-donald-trumps-comedy-central-roast-is-everything-you-thought-it-would-be_us_57fbed42e4b0e655eab6c191
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. “I don’t think we ever got that in writing, but that was definitely conveyed verbally,” Larsen said. In August, Aaron Lee, another roast writer, posted a note on the app Li.st that 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.
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Graff made known that roasters should address Trump only as “Mr. Trump,” according to Larsen.
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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.
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Trump made a few lackluster attempts at cracking wise. He changed a joke meant to slam MacFarlane from: “The only way you’ll ever draw a crowd is with a pencil.” Trump’s revision: “The only crowd you’ll attract is flies.”
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Elsewhere, Trump suggested a broadside against the entire dais: “Their all losers and I like associating with loser because it makes me feel even better about myself.” (The grammar mistakes are Trump’s.)
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“I had to explain to him why he needed to have some jokes about his own hair,” James said. “I said, ‘You have to own it. If you have a great hair joke, you will be impervious to hair jokes.’”
But Trump resisted. In the first draft, he crossed out a joke about needing to feed his squirrel-like bouffant. When the writers kept the joke in for the second draft, he crossed it out again, offering instead this about his hair: “Look how great it looks.”
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.
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“He packed the room with his kind of people,” Joyce said. Trump was himself a difficult participant, according to roast staffers, evincing a palpable resistance throughout the show, wearing a tight smile and avoiding eye contact with the others on the stage. James described his look as ”the scowling curled lip of discontent.”
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