Footage shows President Obama mocking Donald Trump during his speech at the 2011 White House Correspondents' Dinner - but the billionaire didn't look amused.
Now there are suggestions that the event encouraged Trump to run for president.
According to the New York Times, "that evening of public abasement ... accelerated his ferocious efforts to gain stature within the political world."
C-Span Political Editor Steve Scully, who was at the event, told IE: "It was clear that Donald Trump was not happy. He bolted for the exit before the end of the night."
Music mogul Russell Simmons, founder of Rush Card, was sitting at a table near Trump.
"I am sure it got under his skin because it was all truthful," Simmons told IE. "It was not mean spirited but the truth sometimes hurts."
Trump and his wife, Melania, were guests at the glittering affair for the Washington elite.
President Obama started mocking the real estate tycoon mercilessly as soon as he got on the mic. The jabs were mainly for the role Trump was playing in the birther movement that questioned whether Obama was really born in America.
"No one is happier, no one is prouder, to put this birth certificate matter to rest than The Donald," Obama gagged. "That's because he can finally get back to focusing on the issues that matter like did we fake the Moon landing? What really happened in Roswell? And where are Biggie and Tupac?"
Obama didn't hide his utter distain for the reality TV star.
"Obviously we know about your credentials and breadth of experience. For example, seriously, in an episode of Celebrity Apprentice, you, Mr. Trump, recognized that the real problem was a lack of leadership. You fired Gary Busey. And these are the kinds of decisions that would keep me up at night," Obama said to a room full of laughter.
The insults didn't stop with the president. Comedian Seth Meyers was the evening's guest host and he joked: "Donald Trump has been saying that he'll run for president as a Republican, which is surprising, since I just assumed he was running as a joke."
That year's dinner was especially notable because, while Trump was being roasted by the president, the nation was unaware Obama had just given approval for the raid that killed Osama Bin Laden the next day.
Trump on the campaign trail: