Would the night get serious or stay silly? It depended on who you asked.
And it just so happened that the first big name to pose in front of the step-and-repeat was none other than Jimmy Kimmel, the late-night host whose sharp, politically minded monologues criticizing the Cassidy-Graham health-care bill had one attendee branding him a “hero.”
“I don’t know that I am making a difference,” Kimmel said, “but I am going to try. I think if everybody adopts that philosophy we will actually make a difference.”
Kimmel, a self-described Letterman “stalker” (he had the birthday cake and vanity license plate to prove it), kept his material for the night close to the vest but remained characteristically candid about the state of the country.
“I feel hopeful but not necessarily optimistic,” said Kimmel, who planned to hightail it out of Washington after the show. So no quick sit-down with President Trump then?
“Oh, I have a million questions for Donald Trump,” Kimmel said. “I’d need like three hours with him.”
The next few hours, though, could very well be a Trump-free zone.
“No politics tonight,” Martin Short said definitively. Okay then.
Comedian Jimmie Walker, who hired Letterman as a writer when the future late-night host first moved to Los Angeles, said the two don’t ever talk politics.
“Dave is not a political guy,” said Walker, one of the honoree’s oldest industry pals. “He’s not that type of cat.”
Sen. Al Franken (D-Minn.) agrees –sort of.
“No Trump jokes,” Franken said. “This is about David.” But whether Letterman himself is political or not? That’s up for debate, according to Franken, who joked that he tried to get the former TV weatherman to run for office in Indiana (for what position, we don’t know).
“He’s very interested in subjects like climate change,” said Franken, who also saw parallels between Kimmel’s political comedy and Letterman’s, pointing to the former “Late Show” host’s Youtube-able 9/11 monologue as proof.
“[Letterman’s] someone who takes the 60 minutes they have on TV five nights a week very seriously,” Franken added.
Speaking of taking things seriously, finally, here’s the man of the hour himself, making jokes about some serious stuff.
When asked by a reporter on the red carpet how he feels about the current state of affairs in Washington, Letterman deadpans: “I’ll tell you something, if I can be candid — I’m beginning to lose confidence in the Trump administration.”
But seriously, folks: How exactly is Letterman, who famously hates being complimented, taking all this — the praise, the roasting, the fawning?
“It’s uncomfortable,” Letterman said. “So far I’m having a very nice time, but I’m afraid that will all diminish when people are on stage telling lies about me and then I’ll start to wither and become uncomfortable and sweat through my shirt.”
So why do it? Why show up in a tux and subject yourself to a barrage of glittery tributes from the likes of Steve Martin, Amy Schumer, and last year’s Mark Twain recipient, Bill Murray ?
He’s doing it for his 13-year-old son, Harry, who is somewhere in the building.
“With every breath I take, I’m trying to impress him,” Letterman said. “And every now and then I feel like I have to let the young man know that, in fact, his father, not just a dope, but someone in addition to being a dope, was in show business. That’s why I’m doing it.”
The Mark Twain ceremony will air Nov. 20 on PBS.