WEBVTT 00:00:00.000 --> 00:00:01.760 Welcome back to The Deep Dive. We've gathered 00:00:01.760 --> 00:00:04.259 all the sources, the articles, the interviews, 00:00:04.519 --> 00:00:06.960 everything we could find, and we're here to cut 00:00:06.960 --> 00:00:08.720 right through it all. Yeah, get straight to the 00:00:08.720 --> 00:00:11.060 core of what you need to know. And today, we 00:00:11.060 --> 00:00:13.619 are looking at a really fascinating career path. 00:00:13.980 --> 00:00:18.399 Someone who blended history, comedy, and, well, 00:00:18.539 --> 00:00:20.640 a fair bit of improvisation. We're talking about 00:00:20.640 --> 00:00:23.940 Derek Waters? Exactly. Actor, comedian, writer, 00:00:24.140 --> 00:00:27.500 producer, director. The guy wears a lot of hats. 00:00:27.739 --> 00:00:30.160 Best known, of course, for Drunk History. That's 00:00:30.160 --> 00:00:32.200 right. A show that sounds completely ridiculous 00:00:32.200 --> 00:00:35.240 on paper. Historians telling stories while, you 00:00:35.240 --> 00:00:37.700 know, hammered, but somehow became this huge 00:00:37.700 --> 00:00:41.340 award winning thing. So our mission today, pretty 00:00:41.340 --> 00:00:43.039 straightforward. We've got the background, the 00:00:43.039 --> 00:00:45.600 early stumbles, those key partnerships, and then 00:00:45.600 --> 00:00:47.420 the explosion of drunk history. We want to pull 00:00:47.420 --> 00:00:49.159 out the elements that really define his journey. 00:00:49.259 --> 00:00:51.520 And show how this like really unconventional 00:00:51.520 --> 00:00:54.299 idea, something born outside the usual TV machine, 00:00:54.420 --> 00:00:57.600 actually got major, major recognition. And why 00:00:57.600 --> 00:01:00.320 should you listening right now? care about this 00:01:00.320 --> 00:01:03.100 deep dive. Well, think about this. Waters himself 00:01:03.100 --> 00:01:07.000 got eight primetime Emmy Award nominations for 00:01:07.000 --> 00:01:10.180 that show. Eight. That tells you something. It 00:01:10.180 --> 00:01:12.500 really does. This isn't just, oh, here's a funny 00:01:12.500 --> 00:01:16.540 show. It's about how a unique, maybe even quirky 00:01:16.540 --> 00:01:19.840 comedic vision, when it's built on a solid structure, 00:01:20.040 --> 00:01:22.879 can actually win big in the mainstream. It's 00:01:22.879 --> 00:01:25.379 kind of a blueprint. Definitely. So where do 00:01:25.379 --> 00:01:27.239 we start? Okay, let's begin right at the beginning. 00:01:27.480 --> 00:01:30.099 We need to understand the foundation. His early 00:01:30.099 --> 00:01:32.680 life, because honestly, it wasn't the path you'd 00:01:32.680 --> 00:01:35.439 expect for an L .A. comedy guy. All right. So 00:01:35.439 --> 00:01:38.159 we start on the East Coast, mid -Atlantic. Derek 00:01:38.159 --> 00:01:40.299 Waters, born and raised in Lutherville, Maryland. 00:01:40.560 --> 00:01:42.400 Kept a local for school, too, right? Yeah. Attended 00:01:42.400 --> 00:01:44.420 Tyson High School right there in Towson, Maryland. 00:01:45.159 --> 00:01:47.560 Graduated in 98. After that, he did some studies 00:01:47.560 --> 00:01:49.459 at the Community College of Baltimore County. 00:01:49.659 --> 00:01:52.060 OK, so standard East Coast start. Yeah. But the 00:01:52.060 --> 00:01:54.900 sources mention some really crucial personal 00:01:54.900 --> 00:01:57.799 stuff here, things that might explain where his 00:01:57.799 --> 00:02:00.260 creative style comes from. Absolutely. This is 00:02:00.260 --> 00:02:02.340 where it gets interesting beyond just the bio 00:02:02.340 --> 00:02:06.040 facts. We know Waters is Jewish, but maybe more 00:02:06.040 --> 00:02:08.659 significant, especially for his comedy, he's 00:02:08.659 --> 00:02:11.509 dyslexic. And was in special education in school. 00:02:11.689 --> 00:02:13.610 Right. And, you know, we often think of learning 00:02:13.610 --> 00:02:15.949 differences as just hurdles. But for creative 00:02:15.949 --> 00:02:18.449 people, sometimes they force you to find really 00:02:18.449 --> 00:02:22.169 unique solutions. How so? Well, dyslexia, difficulty 00:02:22.169 --> 00:02:25.069 with reading, interpreting symbols, it often 00:02:25.069 --> 00:02:27.889 pushes people to develop these incredibly specific, 00:02:28.270 --> 00:02:31.430 sometimes highly visual or structural ways to 00:02:31.430 --> 00:02:34.389 just process information, to make sense of it. 00:02:34.530 --> 00:02:37.050 Your brain has to build its own order. That makes 00:02:37.050 --> 00:02:38.409 so much sense when you think about Drunk History. 00:02:38.509 --> 00:02:40.509 The whole show is a... about taking total chaos. 00:02:40.550 --> 00:02:42.770 Right. The narrator is slurring, jumping around. 00:02:43.189 --> 00:02:46.310 It's a mess, information -wise. And Waters, as 00:02:46.310 --> 00:02:49.189 the director, the editor, has to turn that auditory 00:02:49.189 --> 00:02:53.560 mess into crystal clear. perfectly structured, 00:02:53.699 --> 00:02:56.680 visually polished reenactments. Exactly. It's 00:02:56.680 --> 00:02:59.039 like he built a career doing professionally what 00:02:59.039 --> 00:03:00.800 his brain maybe had to learn to do personally, 00:03:01.020 --> 00:03:04.020 creating a clear structure to handle messy, complex 00:03:04.020 --> 00:03:07.360 input, managing cognitive chaos, basically. Wow. 00:03:07.580 --> 00:03:09.900 That structural thing feels key. And maybe relying 00:03:09.900 --> 00:03:13.099 on comedic timing, visuals, ways to get ideas 00:03:13.099 --> 00:03:15.639 across quickly when words are tricky. Precisely. 00:03:15.639 --> 00:03:18.539 But this creative path. This wasn't the first 00:03:18.539 --> 00:03:21.479 plan. Not at all. Ah, right. The sports dream. 00:03:21.680 --> 00:03:24.180 Yeah, his first ambition. Professional baseball 00:03:24.180 --> 00:03:26.460 player. The classic story. Focused on sports. 00:03:26.680 --> 00:03:29.780 Wanted to play ball. But then, the big turning 00:03:29.780 --> 00:03:33.020 point didn't make the high school team. Ouch. 00:03:33.639 --> 00:03:36.860 That's a tough public setback for a kid. Demands 00:03:36.860 --> 00:03:39.840 a rethink. And what he did next is really insightful, 00:03:39.960 --> 00:03:42.639 I think. He didn't just, like, quit sports. No. 00:03:42.990 --> 00:03:45.490 What did he do? He became a Little League umpire. 00:03:45.650 --> 00:03:48.229 An umpire. Huh. That's specific. Why that? Think 00:03:48.229 --> 00:03:50.370 about it. He goes from wanting to be the player, 00:03:50.469 --> 00:03:53.169 the center of the action, to being the guy enforcing 00:03:53.169 --> 00:03:56.189 the rules. The impartial observer applying a 00:03:56.189 --> 00:03:58.849 rigid structure. So instead of performing, he's 00:03:58.849 --> 00:04:01.370 managing the performance. Kind of. It's a different 00:04:01.370 --> 00:04:03.729 type of performance, maybe. An umpire is all 00:04:03.729 --> 00:04:05.849 about imposing structure on the game's chaos. 00:04:06.189 --> 00:04:08.509 You need quick judgment, deep understanding of 00:04:08.509 --> 00:04:11.710 the rules, the system. It shows this early fascination 00:04:11.710 --> 00:04:14.330 with... discipline, with systems, even after 00:04:14.330 --> 00:04:17.769 a failure. He chose order over action, in a way. 00:04:17.930 --> 00:04:21.529 That umpire detail, it really lands differently 00:04:21.529 --> 00:04:24.310 now. It foreshadows that structural mindset he 00:04:24.310 --> 00:04:26.750 carries forward. Definitely. And that's the mindset 00:04:26.750 --> 00:04:28.949 he takes when he finally pivots to the arts for 00:04:28.949 --> 00:04:32.149 real. The year after high school, 1999, he makes 00:04:32.149 --> 00:04:34.709 a big move. Heads north, right? To Canada. Yep, 00:04:34.750 --> 00:04:37.850 Toronto. Specifically to attend Second City, 00:04:38.009 --> 00:04:40.389 formal training in sketch and improv comedy. 00:04:40.649 --> 00:04:43.670 Okay, Second City. That's the crucible. That's 00:04:43.670 --> 00:04:45.649 where the structure meets the stage. And Second 00:04:45.649 --> 00:04:48.250 City isn't known for, like, loosey -goosey stuff. 00:04:48.470 --> 00:04:51.569 It breeds disciplined comedians, people who understand 00:04:51.569 --> 00:04:54.569 ensemble work, the game of the scene. Right, 00:04:54.709 --> 00:04:57.050 finding the comedic pattern, repeating it. It's 00:04:57.050 --> 00:04:59.759 all structural, really. Listening, processing, 00:05:00.100 --> 00:05:02.899 integrating chaos like audience suggestions into 00:05:02.899 --> 00:05:04.819 a stable framework. It's the perfect training 00:05:04.819 --> 00:05:07.139 ground for him, setting him up for these high 00:05:07.139 --> 00:05:09.300 -concept, tightly structured formats he becomes 00:05:09.300 --> 00:05:11.220 known for. Okay, so Second City training under 00:05:11.220 --> 00:05:14.819 his belt. Next stop, inevitably, L .A. Right, 00:05:15.040 --> 00:05:17.819 the classic comedian move. Starts the grind out 00:05:17.819 --> 00:05:20.620 in Los Angeles. But his day job, his non -acting 00:05:20.620 --> 00:05:22.300 job, actually tells us something interesting. 00:05:22.540 --> 00:05:25.720 He worked at Tower Video. Tower Video. Wow. Blast 00:05:25.720 --> 00:05:28.250 from the past. Not waiting tables, then. He's 00:05:28.250 --> 00:05:30.769 immersed in movies. Exactly. And the sources 00:05:30.769 --> 00:05:34.089 say he liked the job. Why? Because it exposed 00:05:34.089 --> 00:05:35.910 him to all these independent films he hadn't 00:05:35.910 --> 00:05:39.029 seen. Ah, so not just mainstream Hollywood. He's 00:05:39.029 --> 00:05:41.170 soaking up the indie stuff, the unconventional. 00:05:41.680 --> 00:05:44.579 Maybe roar narratives? Yeah, and that's important. 00:05:44.680 --> 00:05:47.040 It shows this early interest outside the mainstream 00:05:47.040 --> 00:05:50.160 where stories can be more subjective, characters 00:05:50.160 --> 00:05:52.560 maybe a bit messier, structure more experimental. 00:05:52.839 --> 00:05:55.600 It kind of primes him for embracing that sort 00:05:55.600 --> 00:05:57.699 of chaotic reality later, which is the opposite 00:05:57.699 --> 00:06:00.439 of polished network TV. Paves the way for that 00:06:00.439 --> 00:06:02.639 Mark Borchardt influence we'll get to. Okay, 00:06:02.680 --> 00:06:04.959 interesting. So he's in L .A. working at Tower 00:06:04.959 --> 00:06:06.939 Video, starting the performance grind around 00:06:06.939 --> 00:06:09.759 2000. And this is when he forms a really crucial 00:06:09.759 --> 00:06:12.860 partnership. Yes. The comedy duo, Derek and Simon, 00:06:12.980 --> 00:06:15.800 with Simon Helberg. Simon Helberg, pre -Big Bang 00:06:15.800 --> 00:06:18.439 Theory fame. That's the one. And this partnership 00:06:18.439 --> 00:06:20.720 wasn't just about doing sketches together. They 00:06:20.720 --> 00:06:22.420 were smart about how they built their presence. 00:06:22.480 --> 00:06:25.199 They jumped onto the early digital scene. The 00:06:25.199 --> 00:06:27.980 web series, right. Derek and Simon. The show. 00:06:28.350 --> 00:06:30.470 Yeah, and the platform matters here. They were 00:06:30.470 --> 00:06:32.889 on Super Deluxe. Super Deluxe, I remember that. 00:06:33.009 --> 00:06:35.730 It wasn't just YouTube, it was Turner Broadcasting's 00:06:35.730 --> 00:06:37.930 experiment, right? Yeah. Kind of edgy, surreal 00:06:37.930 --> 00:06:40.490 stuff. HBO's parent company trying to figure 00:06:40.490 --> 00:06:43.509 out online comedy. Exactly. Putting their stuff 00:06:43.509 --> 00:06:46.089 there was strategic. It targeted an audience 00:06:46.089 --> 00:06:48.949 that got high concept, maybe slightly absurd 00:06:48.949 --> 00:06:52.790 humor. But even more important, who they made 00:06:52.790 --> 00:06:56.569 it with. Who was that? Bob Odenkirk. Wow, okay, 00:06:56.629 --> 00:07:00.920 Bob Odenkirk? Mr. Show? That's a huge collaborator 00:07:00.920 --> 00:07:04.079 to get early on. Huge. And Odenkirk knows how 00:07:04.079 --> 00:07:07.240 to blend that rapid -fire, chaotic sketch energy 00:07:07.240 --> 00:07:10.439 with a solid structure. Working with him, it's 00:07:10.439 --> 00:07:12.740 a massive stamp of approval. It shows Waters 00:07:12.740 --> 00:07:14.480 is already linking up with people who get that 00:07:14.480 --> 00:07:16.839 blend of absurdity and discipline. The perfect 00:07:16.839 --> 00:07:18.939 kind of mentor for him. So they're doing the 00:07:18.939 --> 00:07:20.899 web series, but also bridging into more traditional 00:07:20.899 --> 00:07:22.620 stuff. Yeah, they made a couple of short films 00:07:22.620 --> 00:07:24.540 that really boosted their profile. What a pity 00:07:24.540 --> 00:07:26.300 card. Derekin Sykes. What a pity card, yeah. 00:07:26.579 --> 00:07:28.779 And look who they got to be in it. Zach Gillifian. 00:07:29.680 --> 00:07:33.920 Whoa. Getting names like Hater and Galafianakis 00:07:33.920 --> 00:07:36.100 in your indie short, that's more than just calling 00:07:36.100 --> 00:07:38.839 in favors. That means respected people thought 00:07:38.839 --> 00:07:41.339 their stuff was genuinely funny and smart. Totally. 00:07:41.480 --> 00:07:44.480 And then another one, Derek and Simon. A bee 00:07:44.480 --> 00:07:47.189 and a cigarette? With Casey Wilson and Emily 00:07:47.189 --> 00:07:49.970 Rutherford. It just showed they had a solid network 00:07:49.970 --> 00:07:53.910 and a style kind of deadpan, awkward relationship 00:07:53.910 --> 00:07:56.370 focus that attracted great talent. And the industry 00:07:56.370 --> 00:07:59.569 proper noticed. Big time. In 2005, Derek and 00:07:59.569 --> 00:08:03.110 Simon landed a pilot deal with HBO. HBO for a 00:08:03.110 --> 00:08:04.990 sketch duo. That's that's a really big deal. 00:08:05.050 --> 00:08:07.269 Premium cable saying, OK, these guys have something 00:08:07.269 --> 00:08:09.149 bankable, something structured enough for us. 00:08:09.209 --> 00:08:11.009 Even if it didn't go to series, getting that 00:08:11.009 --> 00:08:13.569 deal is major validation. For sure. And while 00:08:13.569 --> 00:08:15.410 all this is happening, the West. Web stuff, the 00:08:15.410 --> 00:08:18.069 shorts, the HBO Deal waters is also getting his 00:08:18.069 --> 00:08:21.290 feet wet in traditional TV. Back in 2003, he 00:08:21.290 --> 00:08:24.029 was already co -starring in an ABC sitcom, Married 00:08:24.029 --> 00:08:26.069 to the Kellys. So he wasn't putting all his eggs 00:08:26.069 --> 00:08:28.930 in one basket. He's doing network TV, experimental 00:08:28.930 --> 00:08:31.990 web comedy, premium cable development, all at 00:08:31.990 --> 00:08:34.870 the same time. That versatility is key. He's 00:08:34.870 --> 00:08:36.389 learning all the different languages of comedy 00:08:36.389 --> 00:08:39.169 production simultaneously. All right, let's zoom 00:08:39.169 --> 00:08:41.629 in on Waters just as an actor for a bit. Because 00:08:41.629 --> 00:08:43.889 he worked consistently, right, since the early 00:08:43.889 --> 00:08:48.070 2000s. And his resume is, well, it's long and 00:08:48.070 --> 00:08:50.549 varied. It really is. And that breadth tells 00:08:50.549 --> 00:08:52.990 you a lot. He's got that Second City adaptability. 00:08:53.250 --> 00:08:56.110 He can slot into almost any comedic style, which 00:08:56.110 --> 00:08:58.710 makes him a great supporting player, but also 00:08:58.710 --> 00:09:01.330 hints at why he'd be a good director later, someone 00:09:01.330 --> 00:09:04.190 who understands different comedic rhythms. Okay, 00:09:04.269 --> 00:09:05.889 so let's not just list the shows. Let's think 00:09:05.889 --> 00:09:08.370 about the skills. He was on The League. Right. 00:09:08.470 --> 00:09:10.690 The League is famous for heavy improvisation, 00:09:10.789 --> 00:09:13.789 right? Long riffs, actors having to react and 00:09:13.789 --> 00:09:16.769 build on unexpected lines. How does that connect? 00:09:17.230 --> 00:09:19.509 Well, managing a drunk narrator later, it's kind 00:09:19.509 --> 00:09:20.909 of similar. You're dealing with unpredictable, 00:09:21.330 --> 00:09:23.850 unscripted input, and you have to react, incorporate 00:09:23.850 --> 00:09:26.769 it, keep the scene or the story moving. The League 00:09:26.769 --> 00:09:29.269 was like improv training for managing narrative 00:09:29.269 --> 00:09:31.929 chaos. Okay, interesting. Contrast that with 00:09:31.929 --> 00:09:34.250 something like It's Always Sunny in Philadelphia. 00:09:34.529 --> 00:09:37.889 Much tighter scripting, right? But manic energy. 00:09:38.210 --> 00:09:41.419 Totally different demand. Sonny needs absolute 00:09:41.419 --> 00:09:44.220 commitment to often ridiculous character behavior 00:09:44.220 --> 00:09:46.759 within a very structured, scripted framework. 00:09:47.059 --> 00:09:50.320 That skill playing absurdity with total deadpan 00:09:50.320 --> 00:09:53.419 sincerity is crucial for the drunk history reenactments. 00:09:53.519 --> 00:09:56.419 Right. Because the actors in the reenactments 00:09:56.419 --> 00:09:59.379 are saying these slurred, nonsensical lines, 00:09:59.519 --> 00:10:01.500 but they have to deliver them like serious period 00:10:01.500 --> 00:10:04.240 dialogue. Exactly. The comedy relies on their 00:10:04.240 --> 00:10:06.200 straight -faced commitment. He practiced that 00:10:06.200 --> 00:10:08.620 on Sonny, on Mare and Happy Endings, even on 00:10:08.620 --> 00:10:10.840 broader shows like Suburgatory or The Middle. 00:10:11.019 --> 00:10:14.159 He really did cover the map. Dark cable comedies, 00:10:14.179 --> 00:10:17.600 network family sitcoms like The Middle, the weirdness 00:10:17.600 --> 00:10:20.059 of Santa Clarita Diet. And don't forget his presence 00:10:20.059 --> 00:10:23.200 on those earlier, often edgier platforms. The 00:10:23.200 --> 00:10:26.139 Sarah Silverman. Funnier Dive presents Nick Swartzen's 00:10:26.139 --> 00:10:28.600 Pretend Time. Again, he's consistently popping 00:10:28.600 --> 00:10:30.759 up where comedy is experimenting and evolving. 00:10:31.120 --> 00:10:33.259 He's learning the mechanics. Film roles, too. 00:10:33.360 --> 00:10:35.519 Things like The Brother Solomon, Hall Pass, but 00:10:35.519 --> 00:10:38.120 also your consideration. Ah, the Christopher 00:10:38.120 --> 00:10:40.279 Guest movie? That's a huge signpost. Working 00:10:40.279 --> 00:10:43.659 on a guest set. That's a masterclass in balancing 00:10:43.659 --> 00:10:46.620 improv with rigid adherence to character and 00:10:46.620 --> 00:10:49.559 format. Precision within chaos. Which sounds 00:10:49.559 --> 00:10:52.100 very relevant. But you mentioned a specific voice 00:10:52.100 --> 00:10:54.539 acting role. Yes. This one feels like a perfect 00:10:54.539 --> 00:10:58.480 little precursor. 2012, shut up. Cartoon series 00:10:58.480 --> 00:11:01.740 called Weasel Town. He starred with Jason Ritter. 00:11:01.860 --> 00:11:04.820 Okay. And his character? He voiced Dipster. And 00:11:04.820 --> 00:11:07.580 the description of Dipster is gold. He's described 00:11:07.580 --> 00:11:10.620 as a self -centered, non -sequitur spouting weasel. 00:11:10.759 --> 00:11:13.320 A self -centered, non -sequitur spouting weasel. 00:11:13.340 --> 00:11:15.590 That's... Quite the character description. Isn't 00:11:15.590 --> 00:11:17.889 it great? But analytically, it's spot on. Non 00:11:17.889 --> 00:11:20.110 sequitur spouting. That's delivering controlled 00:11:20.110 --> 00:11:23.149 absurdity. It's chaos. Unrelated bits may be 00:11:23.149 --> 00:11:25.090 delivered with confidence or authority. You got 00:11:25.090 --> 00:11:27.169 the mini drunk history narrator. Pretty much. 00:11:27.250 --> 00:11:30.389 He's practicing taking chaotic auditory input, 00:11:30.470 --> 00:11:32.129 the non sequiturs, and delivering it straight 00:11:32.129 --> 00:11:34.809 or reacting to it straight. It's voice acting, 00:11:34.970 --> 00:11:37.110 yeah, but it's also mastering that structured 00:11:37.110 --> 00:11:39.769 chaos right before drunk history really takes 00:11:39.769 --> 00:11:42.490 off. Okay, wow. So we've got this journey. East 00:11:42.490 --> 00:11:45.350 Coast kid, dyslexia fosters a structural mind, 00:11:45.490 --> 00:11:48.070 fails at baseball, but masters being the rule 00:11:48.070 --> 00:11:50.850 enforcer umpire, finds comedy via disciplined 00:11:50.850 --> 00:11:53.690 improv, grinds it out in LA, proving he can do 00:11:53.690 --> 00:11:56.370 any style on any platform. And all those threads, 00:11:56.529 --> 00:11:59.750 every single one leads directly into the project 00:11:59.750 --> 00:12:02.389 that combined all those skills, right? The defining 00:12:02.389 --> 00:12:06.500 achievement. Drunk history. But again, just like 00:12:06.500 --> 00:12:08.559 his early web work, we have to stress this wasn't 00:12:08.559 --> 00:12:11.059 some polished pitch accepted overnight by a network. 00:12:11.259 --> 00:12:13.799 It grew organically, again, showing how vital 00:12:13.799 --> 00:12:15.659 those non -traditional platforms were for him. 00:12:15.779 --> 00:12:18.080 Let's unpack that origin. Waters co -created 00:12:18.080 --> 00:12:21.700 it, hosts it, ran six seasons, 2013 to 2019 on 00:12:21.700 --> 00:12:24.019 Comedy Central, but started smaller. Much smaller. 00:12:24.200 --> 00:12:26.860 It began as a series of shorts for Funny or Die. 00:12:27.000 --> 00:12:29.009 Funny or Die again. Perfect place to test something 00:12:29.009 --> 00:12:31.490 weird. Exactly. It let him try out this bizarre 00:12:31.490 --> 00:12:33.669 high -concept format without the pressure of 00:12:33.669 --> 00:12:35.809 network notes or needing a huge initial investment. 00:12:36.190 --> 00:12:38.350 The format kind of needs high production value 00:12:38.350 --> 00:12:41.230 for the joke. To land the contrast is key. But 00:12:41.230 --> 00:12:43.029 Funny or Die let him prove the concept first. 00:12:43.129 --> 00:12:45.429 It was a low -risk lab for refining the structure. 00:12:45.889 --> 00:12:47.590 And it got noticed quickly, didn't it? Didn't 00:12:47.590 --> 00:12:49.850 it win something major early on? Yeah, this is 00:12:49.850 --> 00:12:52.970 crucial. Before it was even a TV show, the short 00:12:52.970 --> 00:12:56.090 film version won the jury prize for short filmmaking 00:12:56.090 --> 00:12:58.379 at the Sundance Film Festival. festival Sundance 00:12:58.379 --> 00:13:01.600 that's massive validation it takes this idea 00:13:01.600 --> 00:13:04.679 that sounds frankly kind of lowbrow drunk people 00:13:04.679 --> 00:13:07.799 talking history and proves it has genuine filmmaking 00:13:07.799 --> 00:13:10.860 chomps structure and serious comedic craft behind 00:13:10.860 --> 00:13:13.259 it totally legitimized it so when Comedy Central 00:13:13.259 --> 00:13:15.340 picked it up it already had buzz and credibility 00:13:15.340 --> 00:13:19.259 and then the awards just kept coming 17 primetime 00:13:19.259 --> 00:13:22.429 Emmy nominations for the series overall That's 00:13:22.429 --> 00:13:24.309 staggering for a show like this. It really is. 00:13:24.509 --> 00:13:27.210 Sustained critical acclaim for such an unconventional 00:13:27.210 --> 00:13:30.110 premise. It dominated its niche. And for Waters 00:13:30.110 --> 00:13:33.230 himself, you mentioned eight nominations. Covering, 00:13:33.230 --> 00:13:37.059 acting, writing, producing. Right. Which proves 00:13:37.059 --> 00:13:39.000 he wasn't just the guy introducing the segments. 00:13:39.080 --> 00:13:41.639 He was the driving force, the architect behind 00:13:41.639 --> 00:13:43.899 its success. OK, let's talk about the structure 00:13:43.899 --> 00:13:46.759 of the show itself, because this feels like where 00:13:46.759 --> 00:13:49.679 the dyslexia, the umpire thing, the improv, it 00:13:49.679 --> 00:13:51.899 all comes together. It's totally driven by its 00:13:51.899 --> 00:13:54.960 structure. Waters is the host. Yeah. But he's 00:13:54.960 --> 00:13:57.720 more like the sober anchor in a sea of narrative 00:13:57.720 --> 00:14:00.960 chaos. His job is guiding, managing, editing 00:14:00.960 --> 00:14:03.399 in his head as it happens. It sounds like a nightmare 00:14:03.399 --> 00:14:06.860 directing job, honestly. You take this rambling, 00:14:07.059 --> 00:14:10.740 slurred, subjective story. Full of non sequiturs 00:14:10.740 --> 00:14:12.759 like Dipster the Weasel. Right. And then you 00:14:12.759 --> 00:14:15.779 have to stage these high budget costume drama 00:14:15.779 --> 00:14:19.320 reenactments that perfectly lip sync the drunken 00:14:19.320 --> 00:14:22.179 rambling. But with actors playing it. Totally 00:14:22.179 --> 00:14:25.039 straight. The editing must be intense. The sources 00:14:25.039 --> 00:14:27.259 confirm it's incredibly rigorous. The show is 00:14:27.259 --> 00:14:29.759 like the sophisticated scaffolding. They take 00:14:29.759 --> 00:14:32.379 the messy audio track and Waters' structural 00:14:32.379 --> 00:14:35.019 vision guides them in building this coherent, 00:14:35.259 --> 00:14:38.519 visually polished reenactment around it. So even 00:14:38.519 --> 00:14:40.100 when the narration is falling apart, the visual 00:14:40.100 --> 00:14:42.440 storytelling is rock solid. It's that structure 00:14:42.440 --> 00:14:45.100 again. Exactly. It's imposing order. It's ensuring 00:14:45.100 --> 00:14:47.379 clarity and structure even when the source material 00:14:47.379 --> 00:14:49.889 is pure chaos. So what does this mean for his 00:14:49.889 --> 00:14:52.350 career arc? It feels like he perfectly synthesized 00:14:52.350 --> 00:14:54.649 everything he'd done before into this one thing. 00:14:54.919 --> 00:14:58.000 Absolutely. His second city improv skills helped 00:14:58.000 --> 00:15:00.860 him manage the unpredictable narrators. His decade 00:15:00.860 --> 00:15:02.700 of acting gave him the connections for guest 00:15:02.700 --> 00:15:04.899 stars and the understanding of performance. His 00:15:04.899 --> 00:15:06.840 digital experience taught him how to make things 00:15:06.840 --> 00:15:09.759 punchy and viral. And that underlying need to 00:15:09.759 --> 00:15:11.940 manage information complexity, maybe stemming 00:15:11.940 --> 00:15:14.080 from the dyslexia, drove the whole structural 00:15:14.080 --> 00:15:16.899 approach. Drunk history basically proved that 00:15:16.899 --> 00:15:19.879 you can take a simple, raw, maybe even messy 00:15:19.879 --> 00:15:23.480 idea. And if you execute it with rigorous production 00:15:23.480 --> 00:15:26.539 quality and a strong editorial structure, you 00:15:26.539 --> 00:15:28.600 can create a massive hit that gets mainstream 00:15:28.600 --> 00:15:32.200 awards. The concept sounds chaotic, but the execution 00:15:32.200 --> 00:15:35.559 is pure, disciplined order. Okay, to really get 00:15:35.559 --> 00:15:37.779 inside Waters' head, his specific style, that 00:15:37.779 --> 00:15:40.279 deadpan, observational, but super structured 00:15:40.279 --> 00:15:42.600 thing, we need to look at his influences. Who 00:15:42.600 --> 00:15:44.659 shaped that aesthetic? The sources are pretty 00:15:44.659 --> 00:15:46.299 clear on this. Yeah, this is where it clicks 00:15:46.299 --> 00:15:48.759 perfectly. He names two specific influences, 00:15:48.960 --> 00:15:51.059 and they seem kind of different at first, but 00:15:51.059 --> 00:15:53.200 together they explain drunk history completely. 00:15:53.620 --> 00:15:56.279 Mark Borchardt and Christopher Guest. Okay, let's 00:15:56.279 --> 00:15:59.700 break that down. Christopher Guest, master of 00:15:59.700 --> 00:16:02.440 the mockumentary. Waiting for Guffman, best in 00:16:02.440 --> 00:16:05.179 show. Right. Guest's films are all about precision, 00:16:05.460 --> 00:16:09.299 meticulous detail, great costumes, actors who 00:16:09.299 --> 00:16:11.620 are deeply, sincerely committed to the absurd 00:16:11.620 --> 00:16:14.299 reality of film. The comedy comes from the gap 00:16:14.299 --> 00:16:16.840 between how seriously the form is treated and 00:16:16.840 --> 00:16:20.039 how silly the content often is. So Guest represents 00:16:20.039 --> 00:16:22.200 the look of the reenactments in drunk history. 00:16:22.360 --> 00:16:25.220 Yeah. The polish, the period detail, the serious 00:16:25.220 --> 00:16:28.220 actors. Exactly. Guest is the order. The structure, 00:16:28.379 --> 00:16:30.919 the commitment, the high production value applied 00:16:30.919 --> 00:16:33.059 to the reenactment. Okay, so who's Borchardt? 00:16:33.159 --> 00:16:35.279 Mark Borchardt. He's the subject of that amazing 00:16:35.279 --> 00:16:38.279 1999 documentary American Movie. If you haven't 00:16:38.279 --> 00:16:39.799 seen it, you really should. It's incredible. 00:16:39.879 --> 00:16:43.279 He's this super passionate indie filmmaker from 00:16:43.279 --> 00:16:45.720 Wisconsin trying to make his low -budget horror 00:16:45.720 --> 00:16:49.120 movie coven. Right. Borchardt embodies this raw, 00:16:49.299 --> 00:16:52.039 passionate, sometimes really messy, deeply personal, 00:16:52.179 --> 00:16:55.340 almost chaotic energy. He's the struggling artist, 00:16:55.600 --> 00:16:58.039 pouring his soul into his work against all odds. 00:16:58.220 --> 00:17:00.240 His world is unfiltered, totally subjective, 00:17:00.539 --> 00:17:02.940 incredibly genuine. So Borchardt is the chaos. 00:17:04.079 --> 00:17:07.019 He represents the raw, unfiltered, subjective 00:17:07.019 --> 00:17:10.230 truth of the narration. The drunk storytellers. 00:17:10.230 --> 00:17:12.990 They are Borchardt. They're passionate, trying 00:17:12.990 --> 00:17:15.910 to tell a story, maybe meandering, maybe slurring, 00:17:15.990 --> 00:17:19.089 working with limited resources. You know, it's 00:17:19.089 --> 00:17:23.210 raw and real. Wow. So drunk history forces those 00:17:23.210 --> 00:17:26.549 two worlds together. The Borchardt chaos of the 00:17:26.549 --> 00:17:29.150 narration interpreted through the Christopher 00:17:29.150 --> 00:17:31.210 Guest precision of the reenactment. That's the 00:17:31.210 --> 00:17:33.869 engine. The friction between the messy subjective 00:17:33.869 --> 00:17:36.470 audio and the polished objective visual is where 00:17:36.470 --> 00:17:38.769 all the comedy sparks fly. And this loops back 00:17:38.769 --> 00:17:41.019 to his own story, doesn't it? that early stuff, 00:17:41.180 --> 00:17:44.059 the dyslexia special education. It provides that 00:17:44.059 --> 00:17:46.880 crucial context. Navigating those challenges 00:17:46.880 --> 00:17:49.339 likely gave him this deep, maybe unconscious, 00:17:49.500 --> 00:17:52.240 appreciation for clear communication, for building 00:17:52.240 --> 00:17:54.839 scaffolds to make sense of things. Waters is 00:17:54.839 --> 00:17:56.740 the scaffold. He's the one making sure that even 00:17:56.740 --> 00:17:59.220 when the story itself is a mess, historically 00:17:59.220 --> 00:18:02.079 dubious because of, well, alcohol, the way it's 00:18:02.079 --> 00:18:04.839 delivered is solid, structured, visually engaging. 00:18:05.019 --> 00:18:07.359 He turned a personal challenge into a professional 00:18:07.359 --> 00:18:09.930 superpower. That's the blueprint he offers, really. 00:18:10.230 --> 00:18:12.329 Success didn't come from following the rules. 00:18:12.549 --> 00:18:16.009 It came from taking a unique, simple idea, executing 00:18:16.009 --> 00:18:18.549 it flawlessly, and leveraging the network he'd 00:18:18.549 --> 00:18:21.410 built. Working with Odenkirk early on, the Derek 00:18:21.410 --> 00:18:24.789 and Simon connections, using funny or die that 00:18:24.789 --> 00:18:27.450 let him scale up. He showed that sometimes your 00:18:27.450 --> 00:18:29.390 constraints, learning differences, not making 00:18:29.390 --> 00:18:31.930 the team can actually guide you to leverage your 00:18:31.930 --> 00:18:34.069 unique perspective into something totally unexpected 00:18:34.069 --> 00:18:36.890 and successful. So for you listening, what's 00:18:36.890 --> 00:18:39.839 a takeaway? Waters' career is this amazing example 00:18:39.839 --> 00:18:42.460 of turning a potential vulnerability into a strength 00:18:42.460 --> 00:18:46.019 by mastering structural translation. He wasn't 00:18:46.019 --> 00:18:47.740 the star player. He became obsessed with the 00:18:47.740 --> 00:18:49.440 rules, the structure, the story of the game. 00:18:49.539 --> 00:18:52.079 He didn't conquer TV first. He mastered the new 00:18:52.079 --> 00:18:54.180 digital spaces and used that to break into the 00:18:54.180 --> 00:18:56.460 mainstream on his own terms. Hashtag, hashtag, 00:18:56.460 --> 00:18:58.400 outro. So yeah, we've traced this incredible 00:18:58.400 --> 00:19:01.019 path of Derek Waters. From those East Coast roots, 00:19:01.220 --> 00:19:03.539 the athletic dream shifting towards that structural 00:19:03.539 --> 00:19:06.339 umpire mindset, the disciplined improv training 00:19:06.339 --> 00:19:08.880 at Second City. Then building that L .A. ecosystem 00:19:08.880 --> 00:19:11.680 with Simon Helberg, getting nods from people 00:19:11.680 --> 00:19:14.259 like Odenkirk, proving his versatility as an 00:19:14.259 --> 00:19:17.220 actor across every kind of comedy. Showing he 00:19:17.220 --> 00:19:19.599 could handle the improv chaos of the league just 00:19:19.599 --> 00:19:22.299 as well as the tight scripting of network sitcoms, 00:19:22.299 --> 00:19:24.279 all preparing him for the big one. Which was 00:19:24.279 --> 00:19:28.140 Drunk History. Creator, host, director, synthesizing 00:19:28.140 --> 00:19:31.019 all his skills, imposing that crucial structure 00:19:31.019 --> 00:19:34.240 on narrative chaos, and earning incredible Emmy 00:19:34.240 --> 00:19:36.500 recognition for it. And understanding that unique 00:19:36.500 --> 00:19:39.140 aesthetic comes from blending the raw passion 00:19:39.140 --> 00:19:41.240 of Mark Borchardt with the meticulous precision 00:19:41.240 --> 00:19:44.579 of Christopher Guest, chaos meets order. We also 00:19:44.579 --> 00:19:47.240 saw that pattern. Using platforms like Funny 00:19:47.240 --> 00:19:49.119 or Die, Super Deluxe the unconventional spaces 00:19:49.119 --> 00:19:52.099 to test, refine, and launch ideas before hitting 00:19:52.099 --> 00:19:54.220 the mainstream. Which brings us to that final 00:19:54.220 --> 00:19:56.420 question, something for you to think about. Given 00:19:56.420 --> 00:19:58.619 how Waters used these non -traditional, maybe 00:19:58.619 --> 00:20:00.859 even experimental platforms to launch a hugely 00:20:00.859 --> 00:20:03.900 successful, award -winning show, how has that 00:20:03.900 --> 00:20:06.680 landscape changed today? Yeah, is the next big 00:20:06.680 --> 00:20:09.779 Emmy -winning comedy phenomenon maybe brewing 00:20:09.779 --> 00:20:13.079 right now on TikTok? Or some niche streamer? 00:20:13.180 --> 00:20:15.299 Are the major studios even looking in the right 00:20:15.299 --> 00:20:17.900 places? Find your constraint, build your structure, 00:20:18.039 --> 00:20:21.059 and maybe go make some history. Possibly soberly. 00:20:21.339 --> 00:20:22.579 Thanks for diving deep with us. We'll catch you 00:20:22.579 --> 00:20:22.900 next time.