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  • Seth Weitberg telling the story of Charles Sumner. And proceeding to go full blown Ham and Cheese. While manhandling Waters on a couch.
  • Phil Hendrie describing Daniel Inouye's annoyed response to being told his right arm is gone: "Oh, jeez, this guy with the fuckin' arm, y' love him? I dunno, you wanna go up there and look for it, Billy?"
  • Jen Kirkman launching into a rambling tangent during her summation of Edith Wilson.
    • "Excuse me, it's me, Congress."
      • "Get out of here, Congress."
    • "Congress is like 'Alright... what... ...what... ...what is going on?'."
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    • "Can we come in and see the true condition?"
  • David Wain, in a very subtle CMOF, apparently gets ragingly drunk from a single martini.
  • From "Oklahoma":
    • When Bass Reeves is telling James Fagan his skills and qualifications, he says that he's 390 pounds... prompting Reeves to look confused.
      • And then, there's the capper:
        Bass Reeves: The only thing I can say to you, is... (Beat) (while going to the ground) I'm gonna tape a- take a nap, [bleep] you.
        (cut to Mark Gagliardi collapsing to the ground)
        Derek Waters: (sings) There he goes... On the floor...
      • He spends the rest of the segment on the floor.
    • Mark Gagliardi gets kinda fucked up...
      Mark Gagliardi: He says, "The Bash w-", hold on... "I'm gonna corner their dumb asses while they're sleepin'! I'll sleep you- I will sleep-clack you into my handcuffs, bitches! And I'm gonna grag you- I'm gonna grag you-," hold on. "I'm gonna drag your asses in jail, where I gathered up all the criminals!"
      Derek: That's pretty badass.
      Mark: Listen, mother[bleep], I'll tell you this whole story. Hold on...
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    • Right before the commercial break, Derek goes to the floor to talk to Mark... prompting Mark to do this:
      Mark: ...I love you! (grabs Derek's head to try and kiss him) I love you. I'ma kiss you on the lips.
  • From "New Mexico":
    • While hanging out outside of her house, Fortune Feimster, she points out that, as they were filming, someone drove up to her house and put something in her trashcan. Derek checks it out... and discovers a Wendy's bag containing some... used Wet Ones. How exactly were they used?
      Fortune Feimster: No respect. (to the neighborhood) This is a family neighborhood. You can't just eat Wendy's and masturbate.
    • The fact that Derek dressed himself up in a wolf suit in the story about Lobo and he goes all out Large Ham to play the wolf.
  • From "Inventors":
    • "So this inventor Alexander Graham Bell is like, 'Oh, [bleep], invent the telephone? Yes, please.'"
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    • Apparently, JD Ryznar Alexander Graham Bell hocked up a loogie.
    • At one point, JD Ryznar forgets Alexander Graham Bell's name.
      JD Ryznar: Anyway, what's his name, um... I don't remember his name... Ugh. What's his name? What's the other guy's na- Wilbur? No. Walt Disney? No. (Beat) Telephone.
    • "Who uses the Alexander Graham Bell telephone anymore? Nobody! Except old people... And poor people..."
    • After Mary Phelps Jacob got married to Harry Crosby, he tried to get her to change her name to something like "C. Crosby"...
      Harry Crosby: I would really like it if you change your name to "Clitoris"note .
      Derek Waters: (starts laughing)
      Paget Brewster: It's [bleep]ing true.
    • "Wait, I have to fast forward. I also have to pee."
      Derek: Which one you done do first?
      Paget: No, I have to pee.
      Derek: Okay, well, then pee.
      Paget: (aggressively) I'm gonna.
      Derek: (snickers)
  • From "Space":
    • "If there's any lasting legacy of Wernher Von Braun, it's that he has these amazing ideas, but then he straight up [bleep] up and becomes a Nazi. (chuckles) Like, he's a complicated mother[bleep]."
      • Complemented with the screen briefly turning red and Nathan Fillion (playing Von Braun) giving the camera a evil face.
    • Derek sneezing during a big monologue turns into a routine.
    • "Imagine what it's like to be floating around in the '80s, except this is the '60s."
    • "[Alexey Leonov]'s the first human being to do something."
    • "If we land, and if we land in China, that'll be [bleep] up, because of... something that Wikipedia tells us."
    • At one point, Kyle Kinane just straight up grabs the boom mike.
      Derek Waters: Oh, don't do that. Don't do that.
      Kyle Kinane: I know. I know how TV works.
    • Kyle Kinane describes Siberia:
      Kyle Kinane: All right, they land 2000 kilometers off their mark, in Siberia, which is a real place... In the middle of mating season for wolves and bears. It's below-zero temperatures, wolves, bears, all with just boners...
      Derek: Jesus...
      Kyle: (singing) Looking to [bleep]... (Derek laughs)
  • Only on this show can you have Adolf Hitler be played by "Weird Al" Yankovic.
    If you're unfamiliar with Drunk History and are wondering just what this show is all about, the phrase "'Weird Al' Yankovic as Adolf Hitler" oughta catch you up pretty fast.
  • Lin-Manuel Miranda is interrupted during his story by a FaceTime call from Questlove. We then cut to the historical reenactment, and see Alexander Hamilton, James Monroe, and Aaron Burr taking the same call.
  • Ever wanted to hear Jimmy "Saul Goodman" McGill educate you on "Disco Demolition Night"? Now you can.
    Bob Odenkirk: Well, I guess our story really begins in 1977, with the massive success of "[bleep]ing Disco", which is a terrible form of music.
  • Ashley Nicole Black relates the fateful meeting of Nichelle Nichols and Martin Luther King Jr., wherein King tells Nichols that what she's doing is important, and she shouldn't quit:
    Ashley Nicole Black: And she's all, "Oh fuck. That's a lot. That's a lot. That's, like, a lot on my shoulders. Can you chill?" And he's like, "No. I'm Martin Luther King. I have no chill."
  • From the UK version, Joe Lycett, on the wrong side of a large quantity of prosecco, champagne, and sambuca, tells the story of how notorious London gangsters Ronnie and Reggie Kray were brought down in an operation spearheaded by Leonard "Nipper" Read. The operation suffers an early setback when the Kray twins invite Read into a party he is observing, and his reputation is immediately tarnished by his association with them. According to Joe Lycett, they celebrated their victory with another party. Cut to Ronnie (Dustin Demri-Burns) and Reggie (Seb Cardinal) dancing the twist to a suitably early '60s-sounding instrumental with very serious expressions; Joe mimics this by flailing his arms and legs in his chair. Eventually, Ronnie looks slightly embarrassed and walks out of shot. Reggie lingers for a moment, then begins doing the twist again (complete with the music starting up again), before finally getting a "Yeah, that's probably enough" look and walking off.
  • Anytime Rich Fulcher is narrating.
    • On Abraham Lincoln being mocked by his fellow attorneys:
    Rich Fulcher: Stanton saw Lincoln coming eya- coming up, and Stanton went to Harding "Oh my god, this guy is a lanky, gawky, awkward, ape-legged...ape l- armed...man. This guy is weird. This guy's like an ape. He's got ape arms. He's got like ape-awkward arms. THIS GUY IS LIKE AN APE awkward guy. THIS GUY...IS AN APE...AWK...AWKT...AWKS-WARD! HE'S LIKE AN APE MAN! THIS GUY IS LIKE AN APE-AWKWARD MAN!"
    • On the 1972 Chess Championship with Bobby Fischer, "King of the Chess People":
    Rich Fulcher: In America, it was shown on bars throughout the country, so you would go into a bar, you'd see chess, and not the New York Mets, not the K...Klondike...Bars.
    Derek Waters: But what would you do for a Klondike?
    Rich Fulcher: I would do anything for a Klondike Bar, except Wikipedia my dingus.
    • He spends nearly the entirety of his Lord Gordon Gordon segment with the hiccups.
    • On Mary Shelley coming up with the idea for Frankenstein:
    Rich Fulcher: That night, Mary falls asleep, and has a terrible nightmare. She wakes up with a start and goes, Oh! I have my story! You amazing puppet shits!
    • His inability to say Mary Shelley's pre-marital name. He ends up putting Derek Waters and Kirby Howell-Baptiste in hysterics as the producer keeps trying to get him to say her name right.
    Rich Fulcher: Mary's lover, Percy Shelley, one of the premiere poets-
    Derek Waters: Wait, Percy Shelley? She was in love with someone that had her last name?
    Rich: Two names. Shelley Percy?
    Producer: Uh, Rich, her name is not Mary Shelley before she marries Percy.
    Kirby Howell-Baptiste: (Laughs) Duh!
    Producer: Her name is Mary Wollstonecraft Godwin.
    Derek: (Laughs) Good luck.
    Kirb: Nope! He is not gonna say it!
    Rich: Mary Golonsw-
    Producer: Wollstonecraft Godwin.
    Rich: Okay. Her name is Mary Gollonswogoft.
    Derek and Kirby: (Laughs)
    Producer: Wollstonecraft Godwin.
    Rich: Her name is Mary Wollingodstroft Codwin. And she. Is. Bizarre.
    Derek: (Laughs, gets up and walks away)
    Producer: So, one more time, Mary Wollstonecraft Godwin.
    Derek: (Laughing) There is no...fucking way!
    Kirby: (Laughs)
    Rich: (Laughs) I'll get it! I'm gonna get it!
    Kirby: Why don't you throw in some more consonants, Greg! Okay, we got it, we got it, we got it.
    Derek: What was her name?
    Rich: Okay. Her name...is Wollingonstroft-
    Derek: Mary.
    Rich: Her name is Mary...Wollinstonecroft Godwin. Okay?
    Derek: Gotcha.
  • Derek tried tricking Paul F. Thompkins into drinking to Jim Crow.
  • Apparently, Edgar Allen Poe hated Rufus Griswold so much, he called him a holographic piece-of-shit despite acknowledging that holograms don't exist yet.
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