Not only are the stories themselves often about famous or influential figures emerging triumphant or forgotten yet important moments, but the influence of alcohol leads to them getting told in a very emotional (if incoherent) fashion. Derek Waters stated that part of the process was that the storytellers actually picked the stories that they wanted to tell and found most interesting from a list of topics.
- Mark Gagliardi: You know what, Reeves was the inspiration for The Lone Ranger.
Derek Waters: How come more people don't know Bass Reeves is who inspired The Lone Ranger?
Mark: Because he's Black.
Derek: That's sad. Well, we're changing history now. - Paget Brewster having a genuine heartfelt meltdown over the story of Lyudmila Pavlichenko, especially when she reunites with her old friend Eleanor Roosevelt in the midst of the Cold War.
- Lin-Manuel Miranda telling Christopher Jackson, "Long as I got a job, you got a job." In fact, that entire phone call in general.
- Pretty much the entirety of the history of Mister Rogers' Neighborhood. From the creation of the show, to ten thousand people showing up at Boston fundraiser to support it, to Fred Roger's famous speech at the congressional budget hearings that not only saved the Corporation for Public Broadcasting but increased its budget, it's just one CMOH after another.Solomon Georgio: If it wasn't for what Mr. Rogers did that day, there would have been no Sesame Street, there would have been no Lambchop's Playalong, there would have been no Reading Rainbow. The list just goes on and on and on and on!
- The ending of the Marjory Stoneman Douglas story ends with a direct quote from Douglas, and describes how her spirit lives on in the survivors of the 2018 Stoneman Douglas High School shooting, accompanied by photos from the various March for Our Lives protests.
- At the end of the Martha "the Mouth" Mitchell story, it is noted that at her funeral someone sent a floral sculpture that read "Martha was Right," in reference to how she told reporter Helen Thomas what the Nixon administration was doing to discredit their opponents. She was also imagined to be sweetly lounging in pink luxury while watching the Watergate hearings, after the hell her husband and the administration put her through.
- While discussing Doug Hegdahl's infiltration of the infamous "Hanoi Hilton" POW camp, Mark Gagliardi and Derek take a moment to raise a glass for the late John McCain.
- After Katie Nolan tells the story of Gloria Steinem's undercover exposé of the Playboy Club, she segues into talking about how Steinem paved the way for women like her to be able to be the kind of reporters they wanted, leading to Derek tearing up
in a So Proud of You moment.Katie Nolan: It's tough, but if it weren't for Gloria Steinem, I wouldn't be (air-quoting) "able to be on TV". It's very hard to be a woman that's like 'I love sports!'Derek Waters: But you have stuck to your guns ever since you started. And that...is what...(trails off) - Derek originally planned an episode where narrators would pay tribute to their favorite teachers. The episode would end with him getting drunk with Mr. Stange, the teacher who made him such a history buff, and talking about the Whiskey Rebellion.
- Matt Jones tells the story of Jim Abbott, one of the greatest pitchers in baseball history despite being born without a right hand, and his sheer respect for the man comes through so much that he barely even seems drunk.Matt Jones: Look at your limitations, and say "Fuck you, limitations, I'm gonna do what I want." And that's the American dream.
