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He's a real estate mogul, a reality show pioneer and now a political phenom on his way to becoming the Republican presidential nominee.
And that success sets Donald Trump up for a different role on Saturday night: punch line.
As President Barack Obama polishes his annual -- and final -- tart-tongued stand-up riff for the White House Correspondents' Association dinner, Washington is salivating at the prospect of a sequel to his blistering evisceration of Trump in 2011. The President used that speech to publicly ridicule Trump — who was in the audience — for the billionaire's claims that Obama was not a natural born American and was therefore disqualified from being President.
"Obviously, we all know about your credentials and breadth of experience," Obama said, slamming Trump for his supposed displays of leadership on "Celebrity Apprentice."
"These are the kind of decisions that would keep me up at night. Well handled sir, well handled," Obama said sarcastically.
D.C.'s chance to be hip
The dinner is Washington's annual opportunity to pretend it's hip. Reporters mingle with Hollywood stars, top sports figures, business leaders, administration officials and lawmakers who normally avoid the press. But it's also derided by critics as a sign of an overly cozy cabal of Washington insiders -- frustration that has contributed to the rise of political outsiders like Trump and Democratic presidential contender Bernie Sanders this year.
"Nerd Prom" host Larry Wilmore talks roasting Obama 03:48
In fact, the most unorthodox presidential race in modern history points to a comedy conundrum faced by Obama in his farewell address to the Washington insider love fest that the annual dinner has become. How do you satirize -- and in the process land political blows -- on a campaign that has lifted American politics to new heights of self-parody?
"In some ways it is strange, because this election campaign is so farcical, so exaggerated," said David Litt, who was the lead writer on Obama's White House Correspondent's Association speech between 2012 and last year.
"What outrageous thing can you say about Donald Trump that Donald Trump has not already said?" said Litt, who now runs the Washington operation of the comedy website "Funny or Die."
The media coverage that the dinner now whips up makes it a potboiler of political ambition. Some journalists have suggested that Trump's presidential yearnings began burning brighter in that moment of public humiliation back in 2011.
Whether that's true or not, Trump will not be taking any chances of a repeat -- choosing to stay away from the dinner this year as he campaigns ahead of Tuesday's Indiana primary, which could put him on the path to clinching the GOP nomination. (Sanders will be the only current presidential candidate at this year's dinner.)
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