Welcome back to The Deep Dive. We've gathered
all the sources, the articles, the interviews,
everything we could find, and we're here to cut
right through it all. Yeah, get straight to the
core of what you need to know. And today, we
are looking at a really fascinating career path.
Someone who blended history, comedy, and, well,
a fair bit of improvisation. We're talking about
Derek Waters? Exactly. Actor, comedian, writer,
producer, director. The guy wears a lot of hats.
Best known, of course, for Drunk History. That's
right. A show that sounds completely ridiculous
on paper. Historians telling stories while, you
know, hammered, but somehow became this huge
award winning thing. So our mission today, pretty
straightforward. We've got the background, the
early stumbles, those key partnerships, and then
the explosion of drunk history. We want to pull
out the elements that really define his journey.
And show how this like really unconventional
idea, something born outside the usual TV machine,
actually got major, major recognition. And why
should you listening right now? care about this
deep dive. Well, think about this. Waters himself
got eight primetime Emmy Award nominations for
that show. Eight. That tells you something. It
really does. This isn't just, oh, here's a funny
show. It's about how a unique, maybe even quirky
comedic vision, when it's built on a solid structure,
can actually win big in the mainstream. It's
kind of a blueprint. Definitely. So where do
we start? Okay, let's begin right at the beginning.
We need to understand the foundation. His early
life, because honestly, it wasn't the path you'd
expect for an L .A. comedy guy. All right. So
we start on the East Coast, mid -Atlantic. Derek
Waters, born and raised in Lutherville, Maryland.
Kept a local for school, too, right? Yeah. Attended
Tyson High School right there in Towson, Maryland.
Graduated in 98. After that, he did some studies
at the Community College of Baltimore County.
OK, so standard East Coast start. Yeah. But the
sources mention some really crucial personal
stuff here, things that might explain where his
creative style comes from. Absolutely. This is
where it gets interesting beyond just the bio
facts. We know Waters is Jewish, but maybe more
significant, especially for his comedy, he's
dyslexic. And was in special education in school.
Right. And, you know, we often think of learning
differences as just hurdles. But for creative
people, sometimes they force you to find really
unique solutions. How so? Well, dyslexia, difficulty
with reading, interpreting symbols, it often
pushes people to develop these incredibly specific,
sometimes highly visual or structural ways to
just process information, to make sense of it.
Your brain has to build its own order. That makes
so much sense when you think about Drunk History.
The whole show is a... about taking total chaos.
Right. The narrator is slurring, jumping around.
It's a mess, information -wise. And Waters, as
the director, the editor, has to turn that auditory
mess into crystal clear. perfectly structured,
visually polished reenactments. Exactly. It's
like he built a career doing professionally what
his brain maybe had to learn to do personally,
creating a clear structure to handle messy, complex
input, managing cognitive chaos, basically. Wow.
That structural thing feels key. And maybe relying
on comedic timing, visuals, ways to get ideas
across quickly when words are tricky. Precisely.
But this creative path. This wasn't the first
plan. Not at all. Ah, right. The sports dream.
Yeah, his first ambition. Professional baseball
player. The classic story. Focused on sports.
Wanted to play ball. But then, the big turning
point didn't make the high school team. Ouch.
That's a tough public setback for a kid. Demands
a rethink. And what he did next is really insightful,
I think. He didn't just, like, quit sports. No.
What did he do? He became a Little League umpire.
An umpire. Huh. That's specific. Why that? Think
about it. He goes from wanting to be the player,
the center of the action, to being the guy enforcing
the rules. The impartial observer applying a
rigid structure. So instead of performing, he's
managing the performance. Kind of. It's a different
type of performance, maybe. An umpire is all
about imposing structure on the game's chaos.
You need quick judgment, deep understanding of
the rules, the system. It shows this early fascination
with... discipline, with systems, even after
a failure. He chose order over action, in a way.
That umpire detail, it really lands differently
now. It foreshadows that structural mindset he
carries forward. Definitely. And that's the mindset
he takes when he finally pivots to the arts for
real. The year after high school, 1999, he makes
a big move. Heads north, right? To Canada. Yep,
Toronto. Specifically to attend Second City,
formal training in sketch and improv comedy.
Okay, Second City. That's the crucible. That's
where the structure meets the stage. And Second
City isn't known for, like, loosey -goosey stuff.
It breeds disciplined comedians, people who understand
ensemble work, the game of the scene. Right,
finding the comedic pattern, repeating it. It's
all structural, really. Listening, processing,
integrating chaos like audience suggestions into
a stable framework. It's the perfect training
ground for him, setting him up for these high
-concept, tightly structured formats he becomes
known for. Okay, so Second City training under
his belt. Next stop, inevitably, L .A. Right,
the classic comedian move. Starts the grind out
in Los Angeles. But his day job, his non -acting
job, actually tells us something interesting.
He worked at Tower Video. Tower Video. Wow. Blast
from the past. Not waiting tables, then. He's
immersed in movies. Exactly. And the sources
say he liked the job. Why? Because it exposed
him to all these independent films he hadn't
seen. Ah, so not just mainstream Hollywood. He's
soaking up the indie stuff, the unconventional.
Maybe roar narratives? Yeah, and that's important.
It shows this early interest outside the mainstream
where stories can be more subjective, characters
maybe a bit messier, structure more experimental.
It kind of primes him for embracing that sort
of chaotic reality later, which is the opposite
of polished network TV. Paves the way for that
Mark Borchardt influence we'll get to. Okay,
interesting. So he's in L .A. working at Tower
Video, starting the performance grind around
2000. And this is when he forms a really crucial
partnership. Yes. The comedy duo, Derek and Simon,
with Simon Helberg. Simon Helberg, pre -Big Bang
Theory fame. That's the one. And this partnership
wasn't just about doing sketches together. They
were smart about how they built their presence.
They jumped onto the early digital scene. The
web series, right. Derek and Simon. The show.
Yeah, and the platform matters here. They were
on Super Deluxe. Super Deluxe, I remember that.
It wasn't just YouTube, it was Turner Broadcasting's
experiment, right? Yeah. Kind of edgy, surreal
stuff. HBO's parent company trying to figure
out online comedy. Exactly. Putting their stuff
there was strategic. It targeted an audience
that got high concept, maybe slightly absurd
humor. But even more important, who they made
it with. Who was that? Bob Odenkirk. Wow, okay,
Bob Odenkirk? Mr. Show? That's a huge collaborator
to get early on. Huge. And Odenkirk knows how
to blend that rapid -fire, chaotic sketch energy
with a solid structure. Working with him, it's
a massive stamp of approval. It shows Waters
is already linking up with people who get that
blend of absurdity and discipline. The perfect
kind of mentor for him. So they're doing the
web series, but also bridging into more traditional
stuff. Yeah, they made a couple of short films
that really boosted their profile. What a pity
card. Derekin Sykes. What a pity card, yeah.
And look who they got to be in it. Zach Gillifian.
Whoa. Getting names like Hater and Galafianakis
in your indie short, that's more than just calling
in favors. That means respected people thought
their stuff was genuinely funny and smart. Totally.
And then another one, Derek and Simon. A bee
and a cigarette? With Casey Wilson and Emily
Rutherford. It just showed they had a solid network
and a style kind of deadpan, awkward relationship
focus that attracted great talent. And the industry
proper noticed. Big time. In 2005, Derek and
Simon landed a pilot deal with HBO. HBO for a
sketch duo. That's that's a really big deal.
Premium cable saying, OK, these guys have something
bankable, something structured enough for us.
Even if it didn't go to series, getting that
deal is major validation. For sure. And while
all this is happening, the West. Web stuff, the
shorts, the HBO Deal waters is also getting his
feet wet in traditional TV. Back in 2003, he
was already co -starring in an ABC sitcom, Married
to the Kellys. So he wasn't putting all his eggs
in one basket. He's doing network TV, experimental
web comedy, premium cable development, all at
the same time. That versatility is key. He's
learning all the different languages of comedy
production simultaneously. All right, let's zoom
in on Waters just as an actor for a bit. Because
he worked consistently, right, since the early
2000s. And his resume is, well, it's long and
varied. It really is. And that breadth tells
you a lot. He's got that Second City adaptability.
He can slot into almost any comedic style, which
makes him a great supporting player, but also
hints at why he'd be a good director later, someone
who understands different comedic rhythms. Okay,
so let's not just list the shows. Let's think
about the skills. He was on The League. Right.
The League is famous for heavy improvisation,
right? Long riffs, actors having to react and
build on unexpected lines. How does that connect?
Well, managing a drunk narrator later, it's kind
of similar. You're dealing with unpredictable,
unscripted input, and you have to react, incorporate
it, keep the scene or the story moving. The League
was like improv training for managing narrative
chaos. Okay, interesting. Contrast that with
something like It's Always Sunny in Philadelphia.
Much tighter scripting, right? But manic energy.
Totally different demand. Sonny needs absolute
commitment to often ridiculous character behavior
within a very structured, scripted framework.
That skill playing absurdity with total deadpan
sincerity is crucial for the drunk history reenactments.
Right. Because the actors in the reenactments
are saying these slurred, nonsensical lines,
but they have to deliver them like serious period
dialogue. Exactly. The comedy relies on their
straight -faced commitment. He practiced that
on Sonny, on Mare and Happy Endings, even on
broader shows like Suburgatory or The Middle.
He really did cover the map. Dark cable comedies,
network family sitcoms like The Middle, the weirdness
of Santa Clarita Diet. And don't forget his presence
on those earlier, often edgier platforms. The
Sarah Silverman. Funnier Dive presents Nick Swartzen's
Pretend Time. Again, he's consistently popping
up where comedy is experimenting and evolving.
He's learning the mechanics. Film roles, too.
Things like The Brother Solomon, Hall Pass, but
also your consideration. Ah, the Christopher
Guest movie? That's a huge signpost. Working
on a guest set. That's a masterclass in balancing
improv with rigid adherence to character and
format. Precision within chaos. Which sounds
very relevant. But you mentioned a specific voice
acting role. Yes. This one feels like a perfect
little precursor. 2012, shut up. Cartoon series
called Weasel Town. He starred with Jason Ritter.
Okay. And his character? He voiced Dipster. And
the description of Dipster is gold. He's described
as a self -centered, non -sequitur spouting weasel.
A self -centered, non -sequitur spouting weasel.
That's... Quite the character description. Isn't
it great? But analytically, it's spot on. Non
sequitur spouting. That's delivering controlled
absurdity. It's chaos. Unrelated bits may be
delivered with confidence or authority. You got
the mini drunk history narrator. Pretty much.
He's practicing taking chaotic auditory input,
the non sequiturs, and delivering it straight
or reacting to it straight. It's voice acting,
yeah, but it's also mastering that structured
chaos right before drunk history really takes
off. Okay, wow. So we've got this journey. East
Coast kid, dyslexia fosters a structural mind,
fails at baseball, but masters being the rule
enforcer umpire, finds comedy via disciplined
improv, grinds it out in LA, proving he can do
any style on any platform. And all those threads,
every single one leads directly into the project
that combined all those skills, right? The defining
achievement. Drunk history. But again, just like
his early web work, we have to stress this wasn't
some polished pitch accepted overnight by a network.
It grew organically, again, showing how vital
those non -traditional platforms were for him.
Let's unpack that origin. Waters co -created
it, hosts it, ran six seasons, 2013 to 2019 on
Comedy Central, but started smaller. Much smaller.
It began as a series of shorts for Funny or Die.
Funny or Die again. Perfect place to test something
weird. Exactly. It let him try out this bizarre
high -concept format without the pressure of
network notes or needing a huge initial investment.
The format kind of needs high production value
for the joke. To land the contrast is key. But
Funny or Die let him prove the concept first.
It was a low -risk lab for refining the structure.
And it got noticed quickly, didn't it? Didn't
it win something major early on? Yeah, this is
crucial. Before it was even a TV show, the short
film version won the jury prize for short filmmaking
at the Sundance Film Festival. festival Sundance
that's massive validation it takes this idea
that sounds frankly kind of lowbrow drunk people
talking history and proves it has genuine filmmaking
chomps structure and serious comedic craft behind
it totally legitimized it so when Comedy Central
picked it up it already had buzz and credibility
and then the awards just kept coming 17 primetime
Emmy nominations for the series overall That's
staggering for a show like this. It really is.
Sustained critical acclaim for such an unconventional
premise. It dominated its niche. And for Waters
himself, you mentioned eight nominations. Covering,
acting, writing, producing. Right. Which proves
he wasn't just the guy introducing the segments.
He was the driving force, the architect behind
its success. OK, let's talk about the structure
of the show itself, because this feels like where
the dyslexia, the umpire thing, the improv, it
all comes together. It's totally driven by its
structure. Waters is the host. Yeah. But he's
more like the sober anchor in a sea of narrative
chaos. His job is guiding, managing, editing
in his head as it happens. It sounds like a nightmare
directing job, honestly. You take this rambling,
slurred, subjective story. Full of non sequiturs
like Dipster the Weasel. Right. And then you
have to stage these high budget costume drama
reenactments that perfectly lip sync the drunken
rambling. But with actors playing it. Totally
straight. The editing must be intense. The sources
confirm it's incredibly rigorous. The show is
like the sophisticated scaffolding. They take
the messy audio track and Waters' structural
vision guides them in building this coherent,
visually polished reenactment around it. So even
when the narration is falling apart, the visual
storytelling is rock solid. It's that structure
again. Exactly. It's imposing order. It's ensuring
clarity and structure even when the source material
is pure chaos. So what does this mean for his
career arc? It feels like he perfectly synthesized
everything he'd done before into this one thing.
Absolutely. His second city improv skills helped
him manage the unpredictable narrators. His decade
of acting gave him the connections for guest
stars and the understanding of performance. His
digital experience taught him how to make things
punchy and viral. And that underlying need to
manage information complexity, maybe stemming
from the dyslexia, drove the whole structural
approach. Drunk history basically proved that
you can take a simple, raw, maybe even messy
idea. And if you execute it with rigorous production
quality and a strong editorial structure, you
can create a massive hit that gets mainstream
awards. The concept sounds chaotic, but the execution
is pure, disciplined order. Okay, to really get
inside Waters' head, his specific style, that
deadpan, observational, but super structured
thing, we need to look at his influences. Who
shaped that aesthetic? The sources are pretty
clear on this. Yeah, this is where it clicks
perfectly. He names two specific influences,
and they seem kind of different at first, but
together they explain drunk history completely.
Mark Borchardt and Christopher Guest. Okay, let's
break that down. Christopher Guest, master of
the mockumentary. Waiting for Guffman, best in
show. Right. Guest's films are all about precision,
meticulous detail, great costumes, actors who
are deeply, sincerely committed to the absurd
reality of film. The comedy comes from the gap
between how seriously the form is treated and
how silly the content often is. So Guest represents
the look of the reenactments in drunk history.
Yeah. The polish, the period detail, the serious
actors. Exactly. Guest is the order. The structure,
the commitment, the high production value applied
to the reenactment. Okay, so who's Borchardt?
Mark Borchardt. He's the subject of that amazing
1999 documentary American Movie. If you haven't
seen it, you really should. It's incredible.
He's this super passionate indie filmmaker from
Wisconsin trying to make his low -budget horror
movie coven. Right. Borchardt embodies this raw,
passionate, sometimes really messy, deeply personal,
almost chaotic energy. He's the struggling artist,
pouring his soul into his work against all odds.
His world is unfiltered, totally subjective,
incredibly genuine. So Borchardt is the chaos.
He represents the raw, unfiltered, subjective
truth of the narration. The drunk storytellers.
They are Borchardt. They're passionate, trying
to tell a story, maybe meandering, maybe slurring,
working with limited resources. You know, it's
raw and real. Wow. So drunk history forces those
two worlds together. The Borchardt chaos of the
narration interpreted through the Christopher
Guest precision of the reenactment. That's the
engine. The friction between the messy subjective
audio and the polished objective visual is where
all the comedy sparks fly. And this loops back
to his own story, doesn't it? that early stuff,
the dyslexia special education. It provides that
crucial context. Navigating those challenges
likely gave him this deep, maybe unconscious,
appreciation for clear communication, for building
scaffolds to make sense of things. Waters is
the scaffold. He's the one making sure that even
when the story itself is a mess, historically
dubious because of, well, alcohol, the way it's
delivered is solid, structured, visually engaging.
He turned a personal challenge into a professional
superpower. That's the blueprint he offers, really.
Success didn't come from following the rules.
It came from taking a unique, simple idea, executing
it flawlessly, and leveraging the network he'd
built. Working with Odenkirk early on, the Derek
and Simon connections, using funny or die that
let him scale up. He showed that sometimes your
constraints, learning differences, not making
the team can actually guide you to leverage your
unique perspective into something totally unexpected
and successful. So for you listening, what's
a takeaway? Waters' career is this amazing example
of turning a potential vulnerability into a strength
by mastering structural translation. He wasn't
the star player. He became obsessed with the
rules, the structure, the story of the game.
He didn't conquer TV first. He mastered the new
digital spaces and used that to break into the
mainstream on his own terms. Hashtag, hashtag,
outro. So yeah, we've traced this incredible
path of Derek Waters. From those East Coast roots,
the athletic dream shifting towards that structural
umpire mindset, the disciplined improv training
at Second City. Then building that L .A. ecosystem
with Simon Helberg, getting nods from people
like Odenkirk, proving his versatility as an
actor across every kind of comedy. Showing he
could handle the improv chaos of the league just
as well as the tight scripting of network sitcoms,
all preparing him for the big one. Which was
Drunk History. Creator, host, director, synthesizing
all his skills, imposing that crucial structure
on narrative chaos, and earning incredible Emmy
recognition for it. And understanding that unique
aesthetic comes from blending the raw passion
of Mark Borchardt with the meticulous precision
of Christopher Guest, chaos meets order. We also
saw that pattern. Using platforms like Funny
or Die, Super Deluxe the unconventional spaces
to test, refine, and launch ideas before hitting
the mainstream. Which brings us to that final
question, something for you to think about. Given
how Waters used these non -traditional, maybe
even experimental platforms to launch a hugely
successful, award -winning show, how has that
landscape changed today? Yeah, is the next big
Emmy -winning comedy phenomenon maybe brewing
right now on TikTok? Or some niche streamer?
Are the major studios even looking in the right
places? Find your constraint, build your structure,
and maybe go make some history. Possibly soberly.
Thanks for diving deep with us. We'll catch you
next time.