YMMV / Drunk History

• Heartwarming in Hindsight: Colin Hanks playing Mr. Rogers in the "Underdogs" episode, soon after it was announced his father Tom Hanks would play him in A Beautiful Day in the Neighborhood.
• Ho Yay: Lowered inhibitions plus emotional discussions about topics people are passionate about can lead to...interesting situations:
  • A surprising number of male guests get really touchy-feely with Derek when they're drunk. He's even been kissed on the mouth and invited to share a bathtub.
    J.D. Ryznar: I got at least two bathing suits. Should we put them on and get in the tub?
    Derek Waters: Really?
    J.D. Ryznar: You don't have the balls to get in the tub with me with a bathing suit, do you?
    Derek Waters: ...What? [laughs]
  • Alison Rich and guest host Kirby Howell-Baptiste talk about gay marriage activists Edie Winsdor and Thea Spyer, and decide that they should slow-dance in honor of them. Cut to Alison glomping Kirby and kissing her on the mouth.
  • Jane Levy and Mae Whitman discuss Chicago's Murderess Row, get hammered and get very cuddly with one another. And then this happens:
    Mae Whitman: So he says to her, "I need you to bring me something juicy as hell!" Really get excited about it! Say something sexy! [starts sucking Jane Levy's fingers] Yeah, you know what I mean!
    Jane Levy: [knowing smirk to camera]
  • Played with during an outtake for the Alexander Hamilton episode. Lin-Manuel Miranda sates his munchies with an order of french fries, and Derek leans in to snag a few, causing them to get very up close and personal.
    Lin-Manuel Miranda: [giggling] So, what do I have to do to get a part in this movie?
    Derek Waters: You already got it.
• Questionable Casting: An example where Tropes Are Not Bad; more than a third but less than half the fun is seeing which actor they get for what role, because said actors will almost certainly be totally inappropriate (and in the case of Adolf Hitler, is always cast as a racial or sexual group that Hitler would have hated).
  • Jack Black as Benjamin Franklin, Elvis Presley, and Orson Welles.
  • Michael Cera as Andrew Jackson and Alexander Hamilton.
  • Jim Carrey as Santa Claus.
  • Luke and Owen Wilson as the Kellogg brothers.
  • "Weird Al" Yankovic as Adolf Hitler and Adolf Eichmann.
  • Stephen Merchant as F**kin' Abraham Lincoln.
  • Topher Grace as Milton Bradley.
  • Billie Joe Armstrong as Charlie Chaplin.
  • John Cho as William Shakespeare.
  • Jaleel White as Martin Luther King Jr..
• Retroactive Recognition: Jonah Ray's voice might have already been familiar to Nerdist Podcast listeners in 2014, but his face shows up here a full four years before it became the new face of Mystery Science Theater 3000.
• Seasonal Rot: It's often agreed that the increasingly manufactured and segmented style of the show's later seasons has been to its detriment. This is compounded by the fact that the comedians have obviously started to rehearse their stories many times before they actually tell it, which effectively turns their monologue into an extended stand-up routine and often makes the inebriation a moot point to the performance.
• Suspiciously Similar Song: Season 2's "Hollywood" ends the story of Walt Disney and Ub Iwerks with a piano soundtrack awfully similar to Disney's Leitmotif "When You Wish Upon a Star".
• Tear Jerker: The Hamilton segment casts Burr's downfall in a tragic light, having been goaded into a duel with Hamilton and ruining his reputation. In a posthumous act of spiteful genius, Hamilton wrote his intent to surrender in letters to further condemn Burr. In the final scene, Burr lays a bouquet on Hamilton's grave as a Single Tear rolls down his cheek.

  Lin-Manuel Miranda: Burr was the cautious motherfucker who never let his opinion be known and Hamilton was the reckless motherfucker who let his opinion be known about everything. And in the one moment where it counted most, Hamilton was cautious and Burr was reckless, and that defined their legacies forever. It's fucked up.

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