Unlike the widely-televised White House Correspondents' Association dinner, which Trump made a decision to skip previous year, there are no cameras allowed inside the white-tie Gridiron event.
In a nod to his penchant for over-the-top praise of his accomplishments, Trump said, "My staff was concerned that I couldn't do self-deprecating humor".
Ignoring numerous self-deprecating remarks about his administration, they seem particularly hysterical about Trump's joke that Representative Maxine Waters (D-CA) should take an IQ test.
Trump also raised the not-necessarily comedy-gold subject of the nuclear standoff with North Korea, saying: "I won't rule out direct talks with Kim Jong-un". However, he said it was Kim who faced "the risk of dealing with a madman".
"They've lost a tremendous amount of credibility this year".
Dark days inside the White House as Trump shocks and rages: Philip Rucker, Ashley Parker and Josh Dawsey of the Washington Post write: Inside the White House, aides over the past week have described an air of anxiety and volatility - with an uncontrollable commander in chief at its center. "I feel kind of out of place here", Landrieu said. [Adviser] Steve Miller or Melania?' ...
However, if Saturday night is any indication, were Trump to swap his role as commander-in-chief for comedian-in-chief, he would likely be a cruel, heartless comedian who would "punch down", mocking those already struggling.
"Maybe positive things are happening", Trump said. It's actually been really exciting and invigorating 'cause you want new thought.
Turning to the media, Trump said he and The New York Times are both New York City icons - "the only difference is I still own my buildings". The president said he would sign paperwork detailing these plans this week.
When others were speaking or performing, Trump was reportedly a good sport - laughing and applauding at times during the evening's entertainment.
Arriving late at the Gridiron Club's white-tie dinner, at which dozens of journalists and politicians gather to trade barbs, Trump said he was late because his son-in-law Jarred Kushner could not get through the security.
Ivanka Trump and husband Jared Kushner were in attendance.
Of course, Trump wasn't without harsh words for his Democratic opponents, referring to House Minority Leader Nancy Pelosi as "crazy" and suggesting he would "would kick [Joe Biden's] ass like no other", referring to the former vice president as "sleepy Joe". "Elizabeth Warren", Walker added at the end of the pool report.
Trump using his wife as a punchline is nothing new. Very little. In one job, I had to manage a cutthroat cast of characters desperate for TV time, totally unprepared for their jobs, and each week afraid of having their asses fired. Trump is now a president in transition, at times angry and increasingly isolated. Indicates Broader Inquiry: Mark Mazzetti, David D. Kirkpatrick and Maggie Haberman write of the New York Times write: George Nader, a Lebanese-American businessman, has hovered on the fringes of global diplomacy for three decades. Many have had excellent comic timing.