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The 25 Funniest Drunk History Segments, Ranked

Photo-Illustration: Vulture and Comedy Central/YouTube

In 2007, Derek Waters and Jeremy Konner produced six short sketches for Funny or Die called Drunk History, in which the inebriated retellings of historical events (Edison versus Tesla, the life of Benjamin Franklin) were reenacted with community-theater-level production values, A-list comedians, and total commitment to the storyteller’s every fumbled word and modern vernacular. It was lightning in a bottle, an incredible premise that thrives on the dissonance between the respectability of history and the sloppiness of, well, being drunk.

A few years later, Comedy Central would pick it up as a series that would not only go on to six seasons and 70 episodes but would be nominated for 17 Primetime Emmys, winning one for Outstanding Costumes in a Variety Sketch Series. Yet despite all its success, Comedy Central announced last month that it would be canceling the series.

In the age of streaming and surprise pickups, no show is ever truly dead. But if this is truly the end of Waters’s drunken stumble through the strange corners of American history, we can at least take comfort in the great legacy the show has left behind.

To pay our respects to the series, we set about revisiting nearly all of the show’s 200-ish stories (most episodes feature two to three stories) to find the 25 tipsy retellings that stood above the rest — with Waters himself chiming in with some behind-the-scenes insights from the show’s run.

[Note: We gave oursevles one hard-and-fast rule, which made the creation of this list incredibly complicated: only one story per narrator. This way, each narrator’s entry on the list is a testament to everything they brought to the table across the whole of the show’s mad history.]

25. The Death of Rasputin

Season Five, Episode Two, “Dangerous Mindsâ€

Narrator: Chris Romano

While the season-one story of Romano’s real-life dad, famed arsonist Johnny Cool, nearly made the list, his rambling retelling of the story of Russian Lothario Rasputin’s notoriously laborious murder is too great a match of narrator to ignore. The reenactments match Romano’s fast-talking energy, with Jerry O’Connell’s Rasputin wailing while faux-humping women in a puddle (their naughty bits hidden behind crudely pasted black bars). Plus, unlike all the other times Romano showed the audience his dick, Waters finally joined in on the fun this time (though the show shamefully cut away, the cowards. That’s not what Rasputin would have wanted).

Slip of the Tongue: “I can’t fucking die! I got two fuckin’ dicks!â€

Waters: [That one], I believe, is the most bleeps the show has ever had. I love that one too. Jerry O’Connell and Brendan Sexton III are so good in it. I’m surprised that Johnny Cool [didn’t make it]. I love Johnny Cool. But I respect your decision.

24. The Moulin Rouge

Season Three, Episode 12, “Las Vegasâ€

Narrator: Paul F. Tompkins

Unlike the hoodie and jeans combo we usually see on the show, Paul F. Tompkins tells the story of the first race-integrated casino in Vegas history in his now-ubiquitous tuxedo and bow tie. It’s always a gas to get these bigger names in the narrator’s chair and getting them schnockered, and Tompkins is such an easygoing storyteller, even when fighting off a gargantuan case of the hiccups (and making poor Mort Burke reenact them). “Closed and toes’d†indeed.

Slip of the Tongue: “An integrated casino? I’ve never heard of such a thing — because I’m a racist from the time in which I live!â€

Waters: I’ve been a fan of [Tompkins] from Mr. Show and stand-up, and he’s just a great storyteller. I love that story so much, and, boy, did he get drunk — and, boy, did he dress up.

23. Fred Rogers

Season Five, Episode Six, “Underdogsâ€

Narrator: Solomon Georgio

Before his daddy, Tom, pulled on the crimson cardigan of Fred Rogers, Colin Hanks did the same in a Drunk History as sweet as can be. Chronicling the origins of Mister Rogers’ Neighborhood, and Rogers’s compelling defense of public broadcasting to Congress in 1969, Georgio’s fast-paced, down-to-earth delivery makes for caustic contrast to the overwhelming wholesomeness of Fred Rogers as a man, which dovetails nicely with the cynical world his subject was trying to improve (“We gotta do commercials — cigarettes, alcohol, alcohol made out of cigarettesâ€). Colin’s aw-shucks energy has graced many an episode up to this point, but he fits the loafers of America’s greatest children’s entertainer as confidently as any Hanks could. And it’s great to see the Mister Rogers’ Neighborhood set so lovingly replicated, puppets and all.

Slip of the Tongue: “I can’t believe Mister Rogers would swear.†“Oh, I’m sure he was like flim-flam, ding-dang, goobly-gock, we gotta go back to P-T-Burghy H-E-double hockey sticks.â€

Waters: There’s something so special about that. Also, his dad hadn’t been cast as Mister Rogers yet. When he got cast, Colin told his dad, “Well, I played him first.†Man, the re-creation of that set; the production design was unbelievable. Sometimes [on Drunk History], it makes sense for it to look good — but some things, like [spacecraft], you make funny little models with that. Mister Rogers’ Neighborhood, you’re not going to dumb down the trolley. You gotta make it look as close as you can.

22. The Section 504 Sit-in

Season Five, Episode Five, “Civil Rightsâ€

Narrator: Suzi Barrett

One of Drunk History’s greatest virtues was its desire to center marginalized people in their own stories, which makes its reenactments feel all the more immediate and empowering. So for the story of the pivotal disability-rights protest in 1974, the show cast a host of disabled actors to build its army of protesters, including Tony winner Ali Stroker as Judy Heumann, and YouTube star Zach Anner and Glee’s Lauren Potter as fellow activists. The results are as funny as they are powerful.

Slip of the Tongue: “Why would you want to be on the side of history that categorizes people rather than the side of history that’s, like, liberating and … let’s be the piñata. Let’s make candy.â€

Waters: I’m almost offended — it’s a little high! But that one blows my mind — just how long this country had been going without [disability rights]. The golden rule since day one was “How do we best tell the story?†And we had to tell the story the way we did, with all disabled actors like  Ali Stroker.

21. The Theft of the Mona Lisa

Season Five, Episode Nine, “Heistsâ€

Narrator: Mark Gagliardi

It was so hard not to nominate Gagliardi’s legendary retelling of Stetson Kennedy’s infiltration of the Ku Klux Klan. But if I had to pick one story from Drunk History’s stalwart floor-sitters to revisit, it would be his retelling of Vincenzo Peruggia’s 1911 heist of the Mona Lisa (and the painting’s subsequent rise to notoriety as a result). Jack Black is in top form, lapping up Gagliardi’s Mario-adjacent Italian accent like a plate of spaghett’, and Gagliardi flings himself on couches and floors in a way that makes him one of the show’s most physical performers. But the clincher is that this particular story actually drives Gagliardi to tears.
Slip of the Tongue: “Oh, what a beautiful work of art this woman is [earth-shattering belch].â€

Waters: Jack Black’s performance — him peeping out behind the curtains and running away with the art? Man, that’s great. You like Mona Lisa more than Stetson Kennedy? Wow.

20. The Birth of Hip-Hop

Season Five, Episode Three, “Game Changersâ€

Narrator: Questlove

When you’re telling the story of the birth of hip-hop culture, who better to get than goddamn Questlove? It’s a killer primer on the technical elements of hip-hop — breakdowns, scratching, peekaboos, the Merry-Go-Round theory — and the reenactments hum with funky energy and start-stop dancing. And Questlove scats and beatboxes his way through each development with style, giving DJ Kool Herc (O’Shea Jackson Jr.), Grandmaster Flash (Method Man), and Grand Wizzard Theodore (Miles Brown) plenty to play with.

Slip of the Tongue: “The best babysitter I ever had in my life was my dad’s turntable.â€

Waters: Like I said, it’s always about how you best tell the story; you want to do the birth of hip-hop, it’s gotta be Questlove. Method Man and O’Shea Jackson Jr. are so good. And Miles Brown, he’s not little anymore; that kid’s going to be the biggest star.

19. Nichelle Nichols and Star Trek

Season Five, Episode Three, “Game Changersâ€

Narrator: Ashley Nicole Black

The former Full Frontal correspondent and current Black Lady Sketch Show master only showed up on Drunk History once, but she brought the story of Nichelle Nichols’s pioneering work as Nyota Uhura on Star Trek to vivid life. Raven-Symoné thrives in her beehive and nails that “are way too long for space,†and the TGIF reunion between her and Jaleel White’s MLK is just the icing on the interstellar cake.

Slip of the Tongue: “[Nichols] was like, ‘That’s a lot on my shoulders. Can you chill?,’ and he’s like, ‘No, I’m Martin Luther King. I have no chill.’â€

Waters: Using Raven-Symoné, and Jaleel White, too, there’s so many different levels to that. I got a response from Nichelle Nichols [after the episode] — she was very happy with how it turned out, which was pretty damn cool.

18. The Capture of Adolf Eichmann

Season Five, Episode Nine, “Heistsâ€

Narrator: Rachel Bloom

Crazy Ex-Girlfriend’s Rachel Bloom loves rosé about as much as she loves Nazi-hunting, and, lucky for us, her recounting of the capture of Holocaust architect Adolf Eichmann by the Mossad (or, as Bloom imagines them calling themselves, “The Kidnapping Friendsâ€) has both. Snuggled in a blanket, glass in hand, Bloom’s at her acerbic best, cackling and flinging herself around the couch (“It’s hard to tell a story about Nazis while you’re so cozyâ€) while relishing every outrageous detail of the operation, Weekend at Bernie’s moments and all. And it seems “Weird Al†Yankovic loves playing fake Nazis about as much as Bloom loves pointing out how much her dog licks her genitals.

Slip of the Tongue: “Fuck the Nazis, man. I’m alive. I’m 97.4 percent Ashkenazi.â€

Waters: [on casting Weird Al as a Nazi again] Blame me! Because he played Hitler before; [I got] the greatest person to play the most-hated person in the world. You’ve gotta smile a little bit. That story’s very dark, but, man, it was such an important story that I didn’t know anything about. And [Rachel] did a wonderful job, especially with her dog licking herself. 

17. Maya Lin and the Vietnam War Memorial

Season Five, Episode Six, “Underdogsâ€

Narrator: Jennie Pierson

Pierson’s sprightly, singsong narration is a lovely fit for the tale of how Maya Lin, a 20-year-old Chinese American architect, created the Vietnam Veterans Memorial and changed the way we commemorated American memorial architecture. The reenactments, with Kimiko Glenn and David Harbour, match her energy perfectly, but the real MVP is ensemble member Maria Blasucci’s shrill, dog-eared impression of an irate Ross Perot, who refuses to fund the memorial.

Slip of the Tongue: “I don’t like that it looks like a pee sign — a pee sign? [Laughs.] A peace sign!â€

Waters: Maria Blasucci is the top dollar of that sketch — that’s one of the best performances of the whole show. But that’s also Maria’s talent mixed with Jennie’s talent. What’s that she says? “I’m gonna cut yer fundin’!†I can’t do it. Again, that story was one I didn’t know about before.

16. The Isabella Stewart Gardner Museum Heist

Season One, Episode Four, “Bostonâ€

Narrators: Erin and Michael Rohr

While Drunk History usually leans hard on the storytelling abilities of the professional comedians it puts in the hot seat, one of the show’s best and brightest stories early on came from a random couple Waters interviewed in a Boston bar for the pilot. Together, Erin and Michael Rohr (mostly Erin; Michael chiefly pipes in to try to get a few words in edgewise and clarify details) illustrate the 1990 “art-theft situation†of 13 important works from a Boston museum. It was an early bellwether of the show’s love of literalizing every sound and pew-pew its narrators utter, and Jason Ritter, Martin Starr, and Brett Gelman commit to every hilarious utterance. There’s literally no other Drunk History like it.

Slip of the Tongue: [June Diane Raphael as Gardner, gesturing at a painting] “These are some of the most ext-rens-ive … pieces of world.â€

Waters: That was for the pilot, even though “Boston†aired fifth or sixth, I think. The original idea was to do historical, local, and personal [stories]. If I had to estimate, that was about three to four hours of going around a bar asking people how well they knew that story before I sat down with them. And I just loved how they played off each other. And [Ritter] just nonstop, 100 percent always delivers.

15. The Occupation of Alcatraz

Season Six, Episode Four, “National Parksâ€

Narrator: Daryl Johnson

While Drunk History slipped in its early days with Native American representation in its Lewis and Clark segment (casting Aubrey Plaza and Kumail Nanjiani as Native Americans), it redressed that slipup in funny, respectful fashion with Daryl Johnson’s story of the 19 months during which 89 American Indian activists occupied Alcatraz Island. Adam Beach, Zahn McClarnon, and Q’orianka Kilcher throw themselves into Johnson’s impassioned delivery (aided by Johnson’s chemistry with Eric Edelstein, who guest-hosts in Waters’s stead).

Slip of the Tongue: “We’re gonna take their fresh water. We’re gonna take their electrixity — lemme say that right.â€

Waters: That’s one of my all-time favorites. I remember Zahn wanted to talk to us before we did it because he wanted to be sensitive to Native Americans’ stereotypical association with alcohol. He was very sincere about it. It made me feel so good because he said, “I talked with my mom, and she said, ‘More good than bad will come out of doing this.’†It’s not about how drunk the person is; it’s just a way to get a really important story told to ears and eyes that may not listen to it.

14. Nellie Bly’s Undercover Investigation of Mental Asylums

Season Two, Episode Two, “New York Cityâ€

Narrator: JD Ryznar

In the words of the Gay Men’s Chorus of Los Angeles during the 2020 Film Independent Spirit Awards, “Just all of Laura Dern.†Drunk History sometimes got some really big stars to play ball, but getting the Laura Dern to act out pioneering journalist Nellie Bly’s exposé of the horrid conditions of early-20th-century NYC mental asylums is one of the biggest feathers in the show’s cap. Dern’s wide-eyed interpretation of JD Ryznar’s mumbling baritone as Bly is downright delightful, and bonus points go to getting Dern to bark and growl in time with Ryznar’s li’l pupper to “prove†Bly’s insanity.

Slip of the Tongue: “Listen, stupid 1880s guys with giant mustaches connected to their stupid sideburns: Women … are really cool.â€

Waters: This is nice; it lets me take a step back and say, “Damn, we got to do some cool shit with a lot of neat, really talented people.†We did Nellie Bly twice, and that story, that book, is so powerful. I feel like we’re just about to start talking about mental health, which is crazy, considering how long people have been trying to get conversations going about it. I just felt that story had an importance to it.

13. Percy Lavon Julian

Season Two, Episode One, “Montgomeryâ€

Narrator: Allan McLeod

Allan McLeod’s desert-dry monotone makes for some of the funniest, most endearing episodes in the show’s history; check out his John Wilkes Booth and Jean Lafitte stories if you need more proof. But his magnum opus is probably season two’s recounting of Percy Lavon Julian (a pitch-perfect Jordan Peele), a Black kid growing up in the “Jim Crow segregation land†of Montgomery, Alabama, before becoming the chemist who created synthetic compounds used in just about everything from steroids to birth control. Julian’s contributions to science are so many that McLeod wills a list of all the stuff he created to scroll down the screen (and even grabs and eats one). Plus we get a helpful lecture on the ratio of soybeans to horse dicks.

Slip of the Tongue: “We’re doing real work here, guys. Carbons and hydrodrons, oxyjons and carbutrons. That’s molecules for ya.â€

Waters: Nick Monsour is a great editor, and I’m 99 percent sure he did that episode. But it was the editor’s idea to put all the words there. It was just so funny. But the game of the show is that we’ve got to show whatever they say. And Jordan Peele has the most subtle way of playing that.

12. Orson Welles and Citizen Kane

Season Two, Episode Six, “Hollywoodâ€

Narrator: Steve Berg

Drunk History’s reenactments always had to toe the line between slavish devotion to its time period and the kind of community-theater chintziness that gave the show its unique charm. Here, though, the show poured every bit of period verisimilitude into Berg’s breathless retelling of the origins of Citizen Kane, from the Emmy-winning costumes to cinematography that had to capture both old newsreel footage and Kane’s Expressionistic deep-focus photography. It’s a stellar marriage of subject to presentation and a testament to what the show could do when it really put its mind to it.

Slip of the Tongue: “[Kane] is such a wonderful fucking thing. I love it. Aaaand he also did the voice in the Transformers movie.â€

Waters: That’s the one that won us the Emmy for costumes. One of my favorite things is when John Lithgow and Jack Black are in the elevator, they’re actually in a bathroom standing in a tub. We filmed the narration at the Biltmore with Berg, and the lights kept flickering. I know how to play with my narrators and told him, “I think Orson’s here, man.†But I found out later that was where the Academy Awards were held the year [Welles] won for Kane. Then I was like, Oh shit, he might actually be there.

11. Dolly Parton

Season One, Episode Seven, “Nashvilleâ€

Narrator: Seth Weitberg

The tale of Dolly Parton and Porter Wagoner’s collaboration is a highlight of the show’s first season, throwing Casey Wilson in a blonde wig and Rich Fulcher in Wagoner’s rhinestone-cowboy chic for an invigorating collage of the life of the Queen of Country. So many of Parton’s iconic outfits, magazine covers, and movie posters are lovingly re-created, and we even get an off-key, incoherent rendition of “I Will Always Love You,†which Wilson throws herself into with gusto. It’s a greater tribute to Parton than she could ever ask for.

Slip of the Tongue: “Jolene. Jolene … Jolene? Jolene! Now that is a fucking country-and-western song.â€

Waters: No human being with a heart doesn’t like Dolly Parton. But to think, Oh, I knew she wrote [“I Will Always Love Youâ€], but to find out that it was really a breakup song, is so crazy. We actually got away with using the song because Seth sang it so off-key we were allowed to use it. Seth was a researcher and producer for us; I forget what story we were originally going to do for “Nashville,†but it fell through. He found that story instead, and we just decided to shoot him doing it. I’m so grateful for him for doing that.

10. The Discovery of Cosmic Microwaves

Season Three, Episode One, “New Jerseyâ€

Narrator: Jenny Slate

Jenny Slate’s another Drunk History all-star, and a lot of her stories could have easily made this list (the invention of Coca-Cola was a heavy contender). But she’s never better than when detailing Arno Penzias (Justin Long) and Robert Wilson’s (Jason Ritter) quest to use a listening device made by Bell Labs for NASA to discover the background radiation of the universe. Long and Ritter lean hard into every giggle and hiccup of Slate’s giddy, childlike delivery, and their scale model of the “lonely horn†is one of the show’s neatest props.

Slip of the Tongue: [Talking to her dog] “He’s like, ‘Give me back my balls!’ ‘I can’t. I took them away.’ [Laughs.] But I have a full vagina.â€

Waters: What’s that, like, she yells? There are so many. There are very few people that are more likable than Jenny Slate. I should have rewatched them, but yeah: Jason and Justin Long together. [The invention of] Coke is good, but you picked the right one.

9. Mary Dyer

Season One, Episode Four, “Bostonâ€

Narrator: Jen Kirkman

Jen Kirkman’s the undisputed MVP of Drunk History, having slurred her way through episode after episode, season after season. Balancing a glass of white wine in her hand, she talks us through the story of Mary Dyer, who was hanged in Massachusetts for the crime of being a Quaker. And who better to be her mouthpiece than Winona Ryder, who catches every millimeter of Kirkman’s droll wit, rolling her eyes with the power of every woman who’s had to acquiesce to the feelings of fragile men? Kirkman shouts, she throws pillows, she cries about how many more people visit Jim Morrison’s grave (“And he made horrible music!â€) than Dyer’s. Absolute queen shit.

Slip of the Tongue: “I’m not trying to be a dick, but I’m coming back to ask you: Can you please just have — you don’t have to be, like, into it — but can you please just have religious tolerance?â€

Waters: Another from the pilot, which was called Drunk History Across America, where I had a bus and was going across the country. The whole premise got changed, but that’s a good one. Jen Kirkman is the queen of Drunk History, forever and always. And Winona Ryder, oh my God. And Michael Cera’s dumb wig and his hair coming out.

When we were filming the shot where she’s about to get hanged, you see [that] a van drives by in the back. I remember the first AD yelling, but we were like, “No, please — it’s perfect.â€

8. The Little Rock Nine

Season Six, Episode Three, “Trailblazersâ€

Narrator: Amber Ruffin

I’m sure you’re sensing a pattern here: The best episodes come from the most energetic, enthusiastic performers — sure, you can get away with lollygagging cynicism, but there’s nothing like a breathless recounting of a subject a good speaker is really excited about. That’s never more true than with Late Night With Seth Meyers superstar (and now host of Peacock’s The Amber Ruffin Show) Amber Ruffin, who has never hit a false note in her drunken retellings.

But as much as I love her season-two tale of Claudette Colvin’s inspiration of the bus boycott, the slight edge goes to her recounting of the struggles of the Little Rock Nine in the wake of the 1957 Brown v. Board of Education ruling. With a V-patterned sweater and spicy margarita in hand, Ruffin elucidates, as she is so skilled at doing, the nuances of racist white insecurity in a way that is also adorably hilarious. (“Uh, we don’t like you. You are poopy.â€)

Slip of the Tongue: [As a white Little Rock student] “We don’t know exactly why we hate you. We just know it’s something our parents have handed down to us, and so we’re just acting in what we believe are their best interests.â€

Waters: I’m surprised, man. I like them all, but Claudette Colvin is one of my favorites. But Little Rock is really great.

7. Jack Parsons and L. Ron Hubbard

Season Five, Episode Two, “Dangerous Mindsâ€

Narrator: Duncan Trussell

Trussell’s one of those fascinating dudes who sits somewhere between pop philosopher and conspiracy theorist, which makes him perfect for the Drunk History milieu. The tale of Jet Propulsion Laboratory founder (and sex-magick enthusiast) Jack Parsons is an ideal intersection of Trussell’s niche interests, his cackling befuddlement matched perfectly by a fully committed Taran Killam and Eric Edelstein as L. Ron Hubbard. What better way to highlight the links between America’s space race, Scientology, and orgasmic incantations (apart from a canceled CBS All Access series, that is)?

Slip of the Tongue: “There’s no magical thing here — don’t do speed and fuck with explosives!â€

Waters: No one would tell that story better than Duncan. I think he may have pitched a version of that and then we found this specific story. But Taran Killam is also nonstop, like when he has to hold that sword and say “Om-uh-nam-uh-nam†or whatever gibberish Duncan’s doing. [The sex scenes] were so much fun. We had these broomsticks with wigs on. Just a bunch of teenagers making a little short.

6. Deborah Sampson, the First Female Soldier in U.S. History

Season Five, Episode 1 “Heroinesâ€

Narrator: Paget Brewster

Right up there with Kirkman is the commanding Paget Brewster, who approaches her stories with all the conviction of someone with Something Important to Say. Her Kellogg brothers story (with Luke and Owen Wilson) and invention-of-the-bra story (with Parker Posey) were close candidates, but Brewster and Evan Rachel Wood are a match made in Heaven in this tale about the first woman to take a bullet for America. Decked out in a resplendent fur coat, Brewster absorbs every dad joke Waters can throw at her (“Did she say ‘Oh my gauze’?â€) as she delivers the story with her signature intensity and clarity, like she’s narrating the world’s most informally adapted audiobook. She’s truly a legend in the field.

Slip of the Tongue: [Brewster, after Waters interrupts her] “What the fuck, I’m TALKING TO AMERICA!â€

Waters: Evan Rachel Wood, man, she’s so good. I like to be stupid [with my dad jokes], obviously, but I also love to bother Paget. It’s a very friendly fucking-with-each-other relationship.

5. The Stonewall Riots

Season Four, Episode Three, “Bar Fightsâ€

Narrator: Crissle West

When a Comedy Central show can tell the story of Stonewall more authentically than Roland Emmerich can in a big-budget biopic, you know you’ve got something good. Crissle West’s fierce, impassioned yarn about the June 18 (“or 28th … I know it was one of the eightsâ€) Stonewall riots is one of the show’s best, centering Marsha P. Johnson (Alexandra Grey) and her fellow trans women of color as the pioneers of the queer-rights movement. What’s more, they actually cast trans people like Grey and Trace Lysette in the roles, a move that would be unremarkable if it weren’t so sadly rare. The segment itself is a blast, too, as steeped in its groovy ’70s production as it is committed to West’s immensely likable delivery.

Slip of the Tongue: “Y’all are not going to continue to-to dictrate what our lives are supposed to be like … and as long as we pay taxes, you’re gonna have to listen to what we have to shay — we have to sh — to shay!â€

Waters: I knew I wanted a trans actor to play Marsha P. Johnson, but I wanted to have auditions to make sure I was hiring the right person. [Grey] put in a tape, and I just cried watching it; it was so good. And Trace is in there too. “I’ve got my civil rights!†is so powerful.

That was the last shoot day of that season, and I remember every year feeling like I’m done. And then you do that story, and suddenly you’re like, “There’s more of these, right?â€

4. Alexander Hamilton

Season 4, Episode 9, “Hamiltonâ€

Narrator: Lin-Manuel Miranda

The Tony-winning superstar, no longer young, scrappy, and hungry, decided to go onto Drunk History and offer up a different spin on an American story he has had quite a bit of experience spinning into his own: the rivalry between Alexander Hamilton and Aaron Burr. This time, though, Waters cast the two as women (Alia Shawkat and Aubrey Plaza, respectively), with Miranda giggling through the tale and reciting it with all the excitable spirit he can muster. Since he’s got the whole episode to tell the tale, too, Drunk History gets more room to play within the universe, which leads to one of the more robust stories of the show’s history.

More than the story, though, we get to just spend 20-some minutes in LMM’s presence, which, if you’ve hung out with any theater kid for any amount of time, invariably involves drunken sing-alongs at the piano to “Closing Time†and effusive praise to your friends over speakerphone (“Long as I got a job, you got a job,†he murmurs to Christopher Jackson).

Slip of the Tongue: “Here comes sick-ass Hamilton on a flaming ship — your ass will never be the same.â€

Waters: I think that your No. 4 would be other people’s No. 1. We wanted to do something that was in the same vein [as Hamilton] but not exactly, of course. But getting Bokeem Woodbine as George Washington and mixing the sexes of Hamilton and Burr with Alia Shawkat and Aubrey Plaza, who are two of my favorite people.

3. Rose Valland and The Monuments Men

Season Five, Episode One, “Heroinesâ€

Narrator: Tiffany Haddish

The same year Tiffany Haddish blew up with her star-making turn in Girls Trip, she made her one and only appearance on Drunk History and offered a solid case for herself as one of the best narrators in the bunch. Tackling the story of French museum curator Rose Valland and her attempts to keep Jewish-owned art from falling into the hands of the Nazis, Haddish proves that learning the finer points of WWII history doesn’t have to be boring. (She’s got authority to speak on this subject, too; halfway through the segment, Haddish reveals she’s half Jewish and half Jehovah’s Witness — “a JewJo.â€)

At its heart, Drunk History’s always been about the dissonance between the culturally imparted seriousness we give Important Historical Events and the overwhelming casualness with which the everyday American describes them. Haddish makes the most hilarious case for the value of that sensibility. She’s having a blast, shouting and laughing as she tells the story as only she would tell it. And in doing so, she also opens her audience’s eyes to an unsung heroine who saved French culture from the greedy mitts of evil.

Slip of the Tongue: “And Hitler killed himself … they say. I think he’s hanging out with Tupac.â€

Waters: One of the best narrators in the history of the show. I was so excited to have Tiffany on; I could sit down and listen to her tell any story. The Monuments Men was loosely based on the facts of this story, and we thought we should tell the facts. Tiffany saying “Taking notes, taking notes,†with Busy mouthing it, goes down as not only one of the best narrations but performances as well.

2. Julia Child

Season Four, Episode Nine, “Foodâ€

Narrator: Lyric Lewis

This may not be the best Drunk History nor the most important, but it’s my favorite Drunk History, damn it. Lyric Lewis’s tongue-popping, cool-as-ice delivery is the perfect way to illustrate the life of “dumb, tall†culinary queen Julia Child, resulting in the most consistent laugh-a-minute segment in the show’s history. Michaela Watkins chewing a pencil in lust! Joe Lo Truglio waiting for Lyric to come up with the right milk analogy! Bennie Arthur in a shark outfit! In the narrator’s own words, this segment is “cool cool cool, tight tight tight tight.â€

Slip of the Tongue: [As Child designs shark repellent] “‘I’m not gonna add blood because sharks like blood.’ She adds stuff that’s, like, against blood.â€

Waters: We had a lot of good narrators on the show, but nobody takes the note “Put it in your own words†better than Lyric Lewis.

Julia Child falls into the category of stories we loved to do: “I know this person as one thing but had no idea they also did this.†Julia Child as a spy. If people quote one thing the most from the show, it’s, “Cool cool cool, tight tight tight.†Aasha Davis, one of our amazing ensemble members, made pins that said it — I wear it proud.

1. Mary Shelley and the Creation of Frankenstein

Season Six, Episode One, “Are You Afraid of the Drunk?â€

Narrator: Rich Fulcher

In the realm of Drunk History narrators, no one does it better than Rich Fulcher, whose drunken self is a dead-eyed wit of almost dangerous charm. No one seems to change more when they get wasted as Fulcher does, his mouth tumbling into a whole new vocabulary only the most deranged linguists could conceive, which the dedicated reenactors then have to roll with. Never is that better demonstrated than with the show’s episode-long Are You Afraid of the Dark? riff, where Waters and previous guest Kirby Howell-Baptiste take Fulcher out to the woods to tell the spine-chilling tale of the night Mary Shelley (sorry, Mary Wollstonecraft-Godwin, a name Fulcher tries to pronounce to gut-busting effect) gets the inspiration for Frankenstein at a Lake Geneva getaway.

While Elijah Wood and Jack McBrayer get some fun moments as Percy Bysshe Shelley and Lord Byron, respectively, Evan Rachel Wood once again steals the show with a teeth-gnashing, growling commitment to Fulcher’s every half-conscious grunt and bark. And on top of that, the episode’s scope gives Waters the freedom to cast Will Ferrell and Seth Rogen in a black-and-white story-within-a-story retelling of Frankenstein.

It’s one of the only times the show’s gotten to reenact fiction on top of its gonzo version of history, and the result is one of the hardest-working episodes in Drunk History legend — and the best the show’s ever been.

Slip of the Tongue: [Claire Clairmont on Byron] “I slept with him, and I want to have some more sleeps with him.â€

Waters: That was the most fun and, I think, the most creative the show got — making something that was in the same world but putting a new take on a story within a story, with Rich just out of his damn mind.
Then to have all these amazing actors just read it like Shakespeare was just the coolest thing. I love all the history we do, and the importance of it, but I think we’ve got to put more silly stuff in like that so the show never takes itself too seriously. I hadn’t laughed that hard in a long time.

The 25 Funniest Drunk History Segments, Ranked