“You guys are tough, man!” Wilmore said at one point when his dig at Gov. Chris Christie only produced light laughter. (“Chris lost a lot of weight recently, didn’t he? This is what he said, he said he just eliminated everything from his routine that wasn’t necessary. Like his self-pride and dignity.”)
But that was nothing compared to when he tried out his jokes about the media — to a crowd filled to the brim with journalists.
“Speaking of drones, how is Wolf Blitzer still on television? Ask a follow up question!” Wilmore said of the CNN anchor. “Hey Wolf, I’m ready to project tonight’s winner: Anyone that isn’t watching ‘The Situation Room.'”
On TV, the reaction sounded like hushed murmurs. Our colleagues inside the dinner reported the line bombed. “Boo!” someone yelled. “Hiss!” yelled another.
Wilmore laughed nervously. “No — alright, fine, I like Wolf.” He was booed again when he took another shot at Wolf’s network: “I don’t know about you guys, but I cannot get enough of that CNN countdown clock. Now we can see exactly when they hit zero in the ratings.”
Another joke that didn’t go over so well? “A little bit about me, I am a black man who replaced a white man who pretended to be a TV newscaster,” Wilmore said. “So yeah, in that way Lester Holt and I have a lot in common.”
There were audible, very loud gasps at that joke that obviously called out Brian Williams, replaced by Holt on “NBC Nightly News” after it was discovered he exaggerated or misrepresented stories over the years.
Obama’s more tame jokes about the media fared better than Wilmore’s. Although, after Obama joked that “Jake Tapper left journalism to join CNN,” what sounded quite a lot like a passionate, very loud “booooo” was audible on the video feed, over the more widespread laughter.
On social media, however, there was a much wider range of reactions, suggesting that maybe, just maybe, Wilmore wasn’t there to entertain the people in that room — Wilmore was playing to a different audience, one he had to know was tuning in remotely:
Melissa Harris-Perry, whose messy departure with MSNBC was specifically referenced in the routine (Wilmore says MSNBC now stands for “Missing a Significant Number of Black Correspondents”), tweeted support for Wilmore, which is unsurprising:
While there are plenty of reactions that would reflect the sense in the room that Wilmore was bombing, there are also plenty of tweets that heaped praise on his roasting of the WHCD’s attendees:
The audience also didn’t know what to make of Wilmore’s introduction, when he announced, “Welcome to Negro Night here in Washington. Or as Fox News would report, two thugs interrupted elegant dinner in D.C.” And they really didn’t know how to react when he signed off with a message to Obama: “Yo, Barry. You did it, my n—–. You did it.”
Meanwhile, Wilmore attempted other non-media jokes that drew boos.
“The treasury promised to put Harriet Tubman’s face on the $10 bill but now we have to wait until 2030 for the $20 bill. Man, women haven’t been this deceived by a Bill since Cosby.”
To Obama: “I saw you hanging out with NBA players like Steph Curry, Golden State Warriors. That was cool…You know, it kind of makes sense too, because both of you like raining down bombs on people from long distances.”