Conan on Michelle Obama, Colbert Honored, MattRife plays tennis, and New Comedy Special from David Cross

March 10, 2026

AI Summary

5 min read

Conan O’Brien told Michelle Obama that he is a “51-52 percent optimist” — someone who knows the world has always been filled with horribleness but keeps finding himself just feet from the river, exhausted and ready to give up, only to make it past. He was referencing the 1951 film The African Queen, in which the characters collapse in the woods, convinced they are finished, unaware the river is steps away. “I’ve been there probably 35 times in my life,” Conan said. “Nearly every stage of my career has come with one of those moments.” Critics thought he would not last on late night. Then he got The Tonight Show and thought he was in good shape. “Nope, that blows up and now I thought it’s really over. No, it’s not.” The lesson, he said, is learning to roll with it: “Okay, what’s my next opportunity? Reset ready.” He also acknowledged that his path as a white male coming up in the 1980s and 1990s was a lot easier than it was for many others in comedy. Conan is hosting the Oscars on Sunday.

Colbert Honored at the Writers Guild Awards

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What you'll learn

1 (02:03) **Conan O'Brien on Michelle Obama's Podcast** - Conan discusses his 51/52% optimism philosophy and uses *The African Queen* as a metaphor for career resilience.
2 (03:53) **Stephen Colbert Honored at Writers Guild Awards** - Colbert receives the Walter Bernstein Award for confronting social injustice.
3 (04:47) **David Cross Drops New Special** - *The End of the Beginning of the End* is already out on his website, coming to YouTube April 6th.
4 (05:24) **Cameron Esposito Announces New Album** - *Person of No Consequence* drops March 20th on Special Thing Records.
5 (05:44) **Derek Stroop's Netflix Special *Nostalgic* Out Today** - Part of the Nateland brand, Stroop covers being a 90s kid in rural Alabama.
6 (06:00) **Matt Koff's *Catman* Special Out Today** - The Daily Show writer's special on Veeps covers divorce, middle age, and the bias against men with cats.
7 (06:18) **Mario Adrian's *My Struggle* Special Out Today** - The German-American comedian's special on YouTube tackles German guilt, his Jewish marriage, and LA culture.

+ Full timestamped outline available in the app

Guests on this episode

Conan O'Brien Michelle Obama Stephen Colbert David Cross

Show Notes

Johnny Mac covers Conan O’Brien on Michelle Obama’s podcast discussing optimism, career setbacks, luck, and privilege, and notes Conan is hosting the Oscars with a Hollywood Reporter cover story coming later. He recaps Stephen Colbert receiving the WGA Walter Bernstein Award and joking about Paramount and revolution. New releases include David Cross’s special “The End of the Beginning of the End” (website now, YouTube April 7), Cameron Esposito’s album “Person of No Consequence” (March 20), Derek Stroop’s Netflix special “Nostalgic,” Matt Koff’s Veeps special “Catman,” and Mario Adrion’s YouTube special “My Struggle.” He mentions Kathleen Madigan’s 1978 hoops shoot win and travel sports, Bill Maher getting bumped at a Lakers game, Blake Griffin comparing standup to the NBA, Matt Rife taking a tennis lesson, and Fox News interviewing Iranian-American comic Max Amini on avoiding politics and describing life under Iran’s regime. He closes with a reminder to vote in Comedy Survivor in the podcast’s Facebook group.

00:25 Conan on Optimism
02:20 Colbert WGA Jokes
03:14 New Specials Roundup
05:25 Kathleen Madigan Hoops
06:05 Travel Sports Rant
07:26 McDonalds Order: 2 Cheeseburger Meal, Diet Coke
08:26 Bill Maher Courtside at Knicks-Lakers
09:03 Blake Griffin Standup
09:42 Matt Rife Tennis
11:04 Max Amini on Iran

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This is the animal sanctuary mentioned in the February 10 episode.