Every week, Late Night Last Week highlights some of the best late night TV from the previous week. In this week’s late night TV recap, Conan O’Brien receives the Mark Twain Prize for American Humor, his longtime sidekick Andy Richter discusses Hinge with Taylor Tomlinson, Amber Ruffin goes on Colbert to talk about the WHCA, and Jon Stewart looks at Trump’s first 100 days.
“This is so crazy.”
Such were the words said by Conan O’Brien, under his breath to his wife, Liza, and just barely picked up by a microphone attached to his lapel, at the outset of the ceremony in which the intrepid host received the Mark Twain Prize for American Humor. If anything, the craziest part of the night was how non-gratuitous the whole affair felt. Just like the man himself, it was a brainy, hilarious night that never felt too showy or in-your-face. Everyone got it just right.
Perhaps that is because there have been few comedians of his talent that have been so consistently wrong (O’Brien himself hates this fact, often deflecting again and again by saying just how lucky he is). But while that is true, it was precisely that sentiment with which John Mulaney began the ceremony. After referring to O’Brien as his hero, Mulaney likened his love for Conan to his Chicago Cubs fandom.
“I knew how to root for people that lose constantly,” Mulaney said. “But with Conan, it was likely being a Cubs fan, but you think the way they lost was so brilliant that they won, and you’re trying to convince the scoreboard.”
“It was like being a Cubs fan if after each game, there was a serious discussion as to whether the Cubs should be allowed to be a team anymore,” he added.
The ceremony featured a who’s who of O’Brien’s most popular guests from across his three late night shows, including Saturday Night Live alumni like Tracy Morgan, Adam Sandler, and Will Ferrell. Nikki Glaser came out to remember her father showing her a taped VHS copy of Late Night with Conan O’Brien’s 5th anniversary special. That is, until she was cut-off by one of the show’s most memorable characters, The Interrupter (Brian Stack). Other characters appeared to pay their respects to Conan, including the Masurbating Bear and Robert Smiegel as Triumph the Insult Comic Dog, who emceed the evening.
O’Brien’s acceptance speech began by thanking the man who spoke just before him, David Letterman. He told a story about being rejected as a staff writer on Late Night with David Letterman. For a young, struggling writer, it was a low moment. “Now, imagine that suddenly some angel from the future appears … and tells me that 40 years from now, I’m going to be onstage at the Kennedy Center in Washington and that the most prestigious award in comedy is going to be handed to me by David Letterman,” O’Brien said. “I would have stared at that angel in utter shock and said, ‘Wait a minute. David Letterman is still alive!?’”
Like the literature major he once was, O’Brien ended the speech with a discussion of Twain himself, noting that his body of work was dedicated to rejecting bullies and bigotry, and understanding that to love America is to critique it.
“It has everything to do with comedy. Everything,” he said. “The comedy I have loved all of my life is comedy that is self-critical, deflating, and dedicated to the proposition that we are all flawed, absurd, and wallowing in the mud together.
“Twain is funny and important today because his comedy is a hilarious celebration of our fears, our ineptitude, and the glorious mess of being human,” he added.
The speech ended with Will Forte as Twain dialoguing with Conan from the audience. He then joined Conan on stage, only to then dance alongside others dressed as Twain. There was a lot of speculation during the evening (and even more so given the Trump Administration’s ongoing budget cuts) that this might be the last Mark Twain Prize given. If true, it surely ended on a beautiful note.
Keeping with Conan for a moment, his longtime friend and sidekick Andy Richter delivered a wonderful tribute at the Mark Twain Prize ceremony. Last week, he was also a guest on After Midnight. During the show’s couch segment, host Taylor Tomlinson asked her guests to name something in their lives that has worked out. Richter discussed meeting his wife on the dating app, Hinge.
“How long ago was this?” Tomlinson genuinely asked.
“Just a few years,” Richter said, as Tomlinson stifled a laugh. “It’s not my second marriage. So I’m not a complete winner.”
Tomlinson began to clarify. “No, no no, I didn’t mean anything by it,” she explained. “Anytime single people hear that someone else met someone on a dating app you go, ‘What year?!’ ‘When was it? Because I think it’s [bleep]ing changed.’”
Too true, Taylor. Too true.
Amber Ruffin on the White House Correspondents Dinner
On the April 29 episode of The Late Show with Stephen Colbert, Amber Ruffin, a writer and performer on Late Night with Seth Meyers and co-host of CNN’s Have I Got News For You?, joined to talk about the jokes she would have told at the White House Correspondents Dinner. For those who may have forgotten, Ruffin was disinvited from the dinner more or less because she refused to poke fun at “both sides” equally.
Colbert, who delivered unquestionably the greatest White House Correspondents Dinner performance in history, was the perfect fit to talk with Ruffin about the affair. Ruffin summed up her refusal as such: “We’re at a point where one side is snatching people up off the street and putting them on a plane, and the other side is, you know, not doing that.”
The host then asked Ruffin if she would be willing to share any of the jokes she planned to tell. “Absolutely not,” Ruffin said with a laugh. But she did share the sentiment she planned to convey at the end of the evening: “This administration is trying to get you to hate other people, and that’s not your natural state,” Ruffin shared. “It’s the opposite of what you’re made for.”
“And saying that out loud now,” she added. “Makes me glad that I got canceled.”
Pivoting into the more depressing portion of our program, on The Daily Show last Monday, Jon Stewart marked 100 days of Trump 2.0. With a Rip Van Winkle beard, or as it is now known, the David Letterman beard, Stewart slowly appeared out from behind his desk to update us on all that has happened. “I was kidding he declared,” ripping off the beard. “Energy!”
Stewart had plenty of ire to direct towards Trump. But as always, he is an equal opportunity offender, poking fun at the, well, let’s just say not so forceful response of the so-called opposition party, the Democrats. As he has done often throughout these first 100 days, Stewart took particular issue with Senator Minority Leader Chuck Schumer. He played a clip of Schumer saying they would continue to “keep at it” until Trump’s approval numbers reached below 40%. Those approval numbers, Stewart reminded his audience, “trigger the Schumer fight instinct.”
Well, good news, Stewart shared, Trump is now below 40. “You’ve got ‘em right where you want ‘em!” Stewart shouted into the camera. “Finish him, Schumer! Trump is going after free speech and universities, how will you destroy Trump now that he’s below 40 percent?”
Cut to a clip of Schumer on CNN: “So we sent him a very strong letter just the other day, asking eight very strong questions …”
The audience erupted into laughs fueled by amusement and dread. Stewart, as he is wont to do, donned his Schumer glasses and launched into a short impersonation, before taking off the glasses and simply saying, “God. [Bleep].”
Tough to argue there.
Will DiGravio is a Brooklyn-based critic, researcher, and late night comedy columnist, who first contributed to Paste in 2022. He’s been writing Paste’s late night TV recaps since 2024. He is an assistant editor at Cineaste, a GALECA member, and since 2019 has hosted The Video Essay Podcast. You can follow and/or unfollow him on Twitter and learn more about him via his website.
