Either way, Ms. Wolf, 32, has her work cut out for her.

Washington journalists are a notoriously tough crowd; witness the stony silence that met Stephen Colbert after his blistering 2006 monologue about George W. Bush. The comedian Larry Wilmore, who appeared in 2016, prompted controversy when he used a racial slur in his remarks about Barack Obama.

The coziness of the event — where reporters hobnob with the politicians they cover — can be awkward, too, leading some journalists to stifle their laughter, lest they be caught on camera appearing too gleeful at the president’s expense.

But the dinner can be a proving ground for comics. Hasan Minhaj, last year’s entertainer, received high marks for his balanced performance, coming at the height of tensions between Mr. Trump and the press.

Ms. Wolf, who has also written for “Late Night With Seth Meyers,” recently signed a deal with Netflix to develop a weekly late-night talk show of her own. She gained notice last year for an HBO comedy special, “Nice Lady,” that Jason Zinoman, the comedy critic for The New York Times, praised for its “silly fart jokes tied to meaty social commentaries that spin out into unexpected personal confessions interrupted by nicely crafted one-liners.”

Margaret Talev, a White House reporter for Bloomberg News who is president of the correspondents’ association, said that Ms. Wolf’s “truth-to-power style makes her a great friend to the W.H.C.A.”