Mr. Jost Goes to Washington­­, Like So Many Late Nighters Before Him

It’s a long-standing love/hate relationship: Late-night TV and the White House Correspondents Dinner. It’s love because the reporters want to juice the event with laughs; but the romance sometimes goes sour because they often have trouble deciding: “Is that funny?”

The result? Whichever late-night star accepts the invitation to interrupt the din of political chatter and networking to deliver an array of topical jokes to a massive ballroom with poor acoustics and occasional clattering tableware is going to be hyper-aware that killing in this venue may refer not just to your act but also to your career.

So: Welcome Colin Jost!

For sure, the co-anchor of Saturday Night Live’s “Weekend Update” is a totally logical choice, and his performance on this live Saturday night stage is something to look forward to. Jost brings not only skill at landing potent political jokes with deadpan style, but also plenty of personal charm, which always results in extra applause when he introduces himself on SNL. Extra benefit: His wife might be the biggest celebrity at the event this year. (Jost is married to Scarlett Johansson, if you’re not following closely.)

For those not privileged to hold an invitation to mix with the DC journalistic elite and their celebrity guests, the whole thing can be seen on C-Span, starting at 8pm ET–though you can catch the ever-popular “red-carpet arrivals” on the cable news sets starting at 6.

(The attendees love to call this event “Nerd Prom,” which is the self-conscious way to announce that you’re both smart and cool—so of course a red-carpet march is de rigueur.)

Jost is the latest in a long line of SNL performers who have appeared at the dinner, part of an ongoing competition of sorts with comics from The Daily Show, along with some of the bigger names from the traditional broadcast network late-night shows.

Over the years the SNL names have included Chevy Chase, Al Franken (twice), Darrell Hammond, Norm MacDonald, Seth Meyers, and Cecily Strong. Network late-night stars who have been featured include Merv Griffin, Dick Cavett, Craig Ferguson, Jimmy Kimmel, Conan O’Brien (twice) and Jay Leno (four times.) No, Johnny Carson never appeared, unless you count Rich Little.

Since Jon Stewart rocked the room with a pre-Daily Show appearance in 1997, the Comedy Central franchise has supplied a stream of talent for the event: Stephen Colbert, Larry Wilmore, Hasan Minaj, Michelle Wolf, Trevor Noah, Roy Wood, Jr.

Of course, the central comic tension of the night is how “edgy” will the comic get while skewering the dignitaries on the dais and in the audience, which translates to: Watch yourself, Jack (or, less often, Jill).

A sample of some of the more surgical strikes from WHCD’s past:

Stewart in 1997, on the conformation process: “Weeding out the truly qualified to get to the truly available.”

Wilmore in 2016: “Black Lives Matter is here tonight—I’m just kidding, relax white people.”

Minaj in 2017 (one of three times Donald Trump refused to attend): “We gotta address the elephant that isn’t in the room. The leader of our country is not here. And that’s because he’s in Moscow. It is a very long flight. Vlad just can’t make it on a Saturday.”

Wolf in 2018. addressing Trump press secretary Sarah Huckabee Sanders:  “What is ‘Uncle Tom,’ but for white women who disappoint other white women?”

And the classics:

Meyers in 2011, addressing Trump, there as a celebrity invitee: “Donald Trump has been saying he will run for President as a Republican, which is surprising since I just assumed he would be running as a joke.”

And Colbert in 2006, as his faux conservative character defending George W. Bush’s terrible poll numbers: “We know polls are just a collection of statistics that reflect what people are thinking in reality. And reality has a well-known liberal bias.”

The Meyers joke is still credited (blamed?) for enraging Trump enough that he swore to get revenge by actually running (though it was five years later). Colbert was probably the first performer who was widely criticized for stepping over the line in slicing up a President sitting a few chairs away. Colbert himself has said he thought he might have damaged his career with that performance.

But the opposite happened. Meyers and Colbert set a new standard for the dinner as a unique platform for politically charged jokes. Both men saw their careers raised to a new height.

That was exactly what did not happen for Michelle Wolf, who took much more heat for her stinging shots at Huckabee Sanders, who sat silent and unamused. At least some of the reaction was tied to it being a little unfair to go at a Trump surrogate, even if Trump himself was fair game. (One reason for his permanent boycott of the event.)

The correspondents association was so alarmed by the reaction to Wolf that they responded by having the historian Ron Chernow, of “Hamilton” fame as the dinner’s “entertainer” the next year. Following an edgy, headline-generating comic with a historian is a little like following Richard Pryor with the Disneyland Golden Horseshow Revue.

Which is exactly what the association did in 1969, after Pryor appeared in 1968.

Jost is not wading into as treacherous waters Saturday as other recent hosts. The Biden Administration is not openly hostile to the media. The President himself will show up, undoubtedly with some good material. Perhaps Colin’s biggest challenge will be not overdoing the obvious: Maybe just a couple of age jokes at Biden’s expense?

That territory has been strip-mined down to the earth’s core in late night and elsewhere by this point. Example from Roy Wood Jr last year’s dinner: “In France they rioted when the retirement age went up two years to 64. Meanwhile, in America, we have an 80 year-old man begging us for four more years of work.”

But edgy? Go for it, Colin.