Welcome back to the Deep Dive. Today we are strapping
in for quite a ride looking at a really unusual
career path. I mean one that's been consistently
successful somehow across like two decades and
maybe half a dozen different media platforms
and it's all built on this foundation of two
people who just happen to look exactly alike.
So our mission today based on all these sources
you've gathered is to really unpack the well
The vast, multifaceted career of Randy and Jason
Sklar. Identical coin comedians, actors, everything.
They're kind of the ultimate case study in finding
a super specific niche, right? That spot they
call the intersection of sports, comedy, and
indie rock. We're going to try and map out how
they moved, pretty seamlessly it seems, from
like 90s sitcoms and stand -up. all the way to
guest spots on shows like Better Call Saul and
building this whole podcast empire along the
way. It's fascinating, isn't it? It's not just
the sheer amount of stuff they've done, the breadth
of it all. It's the foresight, maybe, the adaptability
you'd need to jump between platforms like that
and keep your core brand solid. We're talking
about a career that goes from hosting cheap seats
on ESPN Classic, which was pretty niche. Yeah,
I love that show. doing really deep personal
stuff on NPR's This American Life and like winning
awards for web series way back when nobody was
really doing that. So succeeding in stand up
and sports commentary and this long form podcasting
thing, it just shows how resilient that unique
twin host identity really is. That kind of media
hopping and sustaining it. That's incredibly
rare. Okay, let's get into it. Let's unpack this.
Start with the basics, their identity, where
they came from, and how that twin thing first
became a professional tool. All right, so these
guys, they're real Midwesterners, born January
12, 1972. St. Louis, Missouri, grew up in the
suburbs, Jewish family. And what's interesting,
the sources say the comedy decision wasn't like
a whim after college. It was something they decided
on and really firmed up during their time at
the University of Michigan. Both went there,
both in Alpha, Epsilon, Pi. Right, that shared
experience, that shared goal in Ann Arbor that
really set the stage. They didn't just, you know,
wait around for an opportunity. They went out
and made one. So 1994, they've got their degrees,
but they're clearly focused on performing. They
make that move, the classic move. To New York
City. And that's where they started hammering
out that style, you know, that coordinated back
and forth, super high energy stand up thing and
all the clubs and that environment. It kind of
forced them pretty quickly to figure out how
to use their biggest asset. The fact that they
were identical, that synchronized thing. And
it worked, didn't it? Yeah. That New York grind
paid off surprisingly fast. Got them that first
big TV break. Crucial one. Established them as
writers and performers. It was 97, right? With
that MTV show. App2F. Short -lived, but pretty
influential from what I gather. Oh yeah, we need
to pause on App2F for a sec. Even though it was
just one season, you gotta understand why it
mattered so much. Late 90s MTV. They were trying
all sorts of things, right? Blending sketch,
stand -up, sitcoms, trying to grab that young
audience. App2F gave young comics this huge national
stage, and for the Sklars, starring in it, writing
for it. It let them show off their writing chops
and that twin dynamic. all at once it wasn't
just a break it was like a national audition
tape that said hey these guys are a package deal
and they're smart they're funny they get it that
makes sense that early exposure kind of moved
them beyond just being oh look twins you know
made them into something casting directors could
actually use and when you look at their acting
roles that twin status is often right there at
the center sometimes taken to like really wild
extreme exactly casting directors saw the shortcut
the narrative shorthand they offered like the
most memorable early example maybe the weirdest
is when they played conjoined characters think
about uh the oblongs that animated show they
did eight episodes as biff and chip oblong wait
conjoined twins yeah playing conjoined characters
instantly gives you this level of like physical
comedy and weird relationship stuff that's hard
to get any other way and they did it again didn't
they in live action on gray's anatomy peter and
jake weitzman that's the one one episode but
super memorable it's a casting choice that's
inherently specific you know memorable physically
demanding Plays right into that weird kind of
synergistic humor they have. But it wasn't always
about being literally attached, right? They could
use that twin dynamic in other ways. No, definitely
not always attached. They're great in those recurring
duo roles where they're basically two halves
of the same personality coin. Perfect example,
Better Call Saul. Season three, they run that
music shop, ABQ and Tune. Oh, those guys. Yeah,
they were brilliant. When Jimmy's suspended trying
to make commercials. Exactly. And the humor comes
from their specific energy. Right. Slightly aloof,
perfectly in sync. These kind of quirky small
business owners. Yeah, that was great casting.
And it keeps happening. The sources show this
dynamic is still getting used today in big comedies.
They popped up as Kobe and Bran on What We Do
in the Shadows in 2022. Right. And they're going
to be Ryan and Brian on Night Court in 2025.
So whether it's an obscure music shop in Albuquerque
or dealing with vampires on Staten Island. Their
identity as the twins, this like stable, built
-in comedic unit, that's the key thing for casting.
Gives you immediate visual clarity, relational
dynamics. Very few other actors can just bring
that. And I think that energy, that synchronized
delivery, that rapid fire thing, they honed in
acting and sketch. That feels like the perfect
training ground for what came next. Right. The
whole sports commentary world. That's absolutely
spot on. That quick witted back and forth practice
over years of stand up and sketch. It translated
perfectly into the rhythm, the demanding pace
of sports media. OK, so this is where it gets
really interesting, I think, where they carved
out that signature niche, that brand identity
that's lasted this like. deep dive into merging
comedy and sports yeah the commitment to it is
pretty remarkable and it found its like perfect
tv home with cheap seats ran 2004 to 2006 on
the espn classic four seasons became this huge
cult hit and the premise was so simple but uh
strategically brilliant, they played these fake
ESPN research assistants. Right, down in the
archives. Exactly. And their job was just to
provide this rapid fire, funny commentary on
the weirdest, sometimes the most obscure historical
sports moments from ESPN's massive library. You
know, the stuff gathering dust. He was definitely
must -see TD for a certain type of sports fan.
Yeah. The kind who appreciated the absurdity
of it all. But let's dig into the structure for
a minute because this connects them to something
bigger in comedy history. Your sources are clear.
Cheap Seats basically lifted its format directly
from Mystery Science Theater 3000. Oh, explicitly.
Yeah. They took that whole riffing on bad media
framework and just applied it wholesale to old
sports highlights, bloopers, weird forgotten
games. The MST3K connection is huge. It really
is. And the beauty of it was how it sort of legitimized
sports fandom as a topic for smart comedy. They
weren't just laughing at a bad game. They were.
analyzing the inherent weirdness of it all the
human failings captured on tape and the tone
was key it was super enthusiastic like they genuinely
loved this stuff Deeply knowledgeable, but also
totally irreverent. The pacing was just relentless.
Perfect for their twin dynamic. Setting up jokes,
spiking them, finishing each other's sentences.
Total sync. Yeah. That was basically the practice
field, the high -speed training for all their
later podcast work. That rapid -fire riffing.
And the ultimate validation, the seal of approval,
came from the MST3K guys themselves, didn't it?
It absolutely did. They didn't just approve.
They kind of formalized it. Season 2 opener of
Cheap Seats, the original MST3K. MST3K characters
Mike Nelson, Crow T -Robot, Tom Servo showed
up in silhouette. Yeah. Making fun of the Sklar's
own host segments. And the sources point out
this is actually a pretty big deal in comedy
history. It was the only time those specific
characters and actors, Mike Nelson, Bill Corbett,
Kevin Murphy, appeared together as the MST3K
cast after the original show got canceled. Wow.
It's like getting knighted by comedy royalty.
Pretty much. Confirmed they'd mastered the format,
earned the right to, you know. Carry that torch.
Incredible. OK, so beyond ESPN Classic, their
sports media footprint is also really tied up
with Jim Rome, right? Yeah. That whole connection,
the Jim Rome cinematic universe, as you called
it. Huh. Yeah. That connection was vital. It
gave them consistent high volume stage time,
basically. Which you need to keep your comedy
sharp. They were constantly filling in as guest
hosts on his syndicated radio show, first Premier
Radio, then CBS Radio. Think about that, stepping
into that intense hot take radio environment
day after day and holding that audience. It's
a totally different skill than scripted TV. And
Randy specifically was on Rome's ESPN TV show,
Jim Rome is Burning. A lot, right? As a forum
guest. Numerous times, yeah. That constant visibility
on all of Rome's platforms really cemented them
in the minds of sports fans as these reliable,
sharp, funny voices commenting on sports absurdity.
And it all kind of culminated with that recurring
segment they had on Rome on Showtime called Sklard
for Life. Sklard for Life, perfect name. And
that segment was basically... Just roasting the
craziest sports adjacent stories of the month.
Exactly. Rome would tee up the six to eight weirdest
stories, sports screw ups, arrests, viral clips,
weird photos. And the brothers would just go
to town on them, skewer them with that signature
energy. Showtime gave them that premium cable
visibility, too. Right. Put them in front of
a, you know, maybe a slightly more sophisticated
sports audience. Reinforce that brand. The go
to comedians for analyzing sports culture's weird
side and doing that. regularly having to come
up with fresh sharp commentary on topical stuff
under pressure that was essential practice for
the conversational flow of podcasting that ability
to just riff endlessly on some dumb news story
they were perfecting it right there and we can't
forget their roots gotta mention their st. Louis
pride and that ESPN to special utility men The
quest for Cooperstown. Oh, yeah. Utility Man.
That special perfectly captures their whole thing,
doesn't it? Their hometown pride, their deep
knowledge of niche sports history and their stand
up sensibility all rolled into one. Yeah. It
was this like funny but genuinely passionate
attempt to argue for Jose Okendo, the Cardinals
utility player, to get into the Baseball Hall
of Fame. Only they would do that. Exactly. It's
the perfect niche comedy subject. They weren't
making fun of the Hall of Fame. They were celebrating
this obscure player that. that only true hardcore
fans would even know, let alone champion. That
mix of championing something, celebrating it,
but also critiquing it with humor. It built this
brand that felt really authentic to fans, I think.
It wasn't just jokes about sports. It was comedy
from diehard, knowledgeable fans. Totally. And
all this work, this high -volume, rapid -fire
riffing practice, it just set them up perfectly
for that next big media shift. Podcasting. Yeah,
looking at their career path, that move into
podcasting. It was a... really smart business
decision. Masterful, even. All that earlier work,
the casual riffing style from Cheap Seats, the
constant radio hosting with Rome. It was basically
like a decade -long boot camp for the podcast
format, long -form conversational. And podcasting
gave them two really crucial things. One, much
deeper engagement with their fans. And two, maybe
more importantly, total creative freedom. No
network notes. And that strategic move led straight
to their big one, their flagship show, Scarborough
Country. August 2010, right, on Earwolf, which
was pretty cutting edge back then. Ran strong
until 2017. They were definitely early adopters.
And they defined the show so specifically. The
intersection of sports, comedy, and indie rock.
That specificity is so key. It wasn't just a
comedy podcast. It was aimed squarely at this
like culturally savvy listener, someone who might
care about the NFL playoffs and the new Spoon
album. And that niche, it actually attracted
a pretty mainstream audience, but still felt
authentic to their core fans. You see it in the
guest list, right? Spanned comedy and sports.
Yeah, huge names. Jon Hamm, Terrell Owens, Rich
Eisen. Patton Oswalt, Adam Carolla, Diablo Cody.
Even Richard Simmons. Wow, Richard Simmons. That's
a get. Right, and the quality was recognized.
2012, Sklarbro Country gets nominated for Best
Podcast at the Comedy Central Comedy Awards on
TV. That's big. Solidified them not just in sports
media, but in the mainstream comedy world, too.
But here's where you see the business brain working
again. They saw the value in, like, more listener
touch points and maybe testing out a spinoff
format that didn't rely so heavily on booking
those huge guests every week. So summer of 2012,
they launch a second show, Sklarbro County. Right.
The shorter midweek snack episode, they called
it. Which feels like. A smart move. Keep people
engaged midweek. And they brought in Dan Van
Kirk as a co -host, right? Yeah, Dan Van Kirk,
up -and -coming character comic. Bringing him
in was key. And the premise for County shifted,
moved away from the sports analysis, more towards
just pure chaos, pure absurdity. Van Kirk's job
was basically to find these insane news stories,
people doing incredibly dumb or silly things,
and the sclars and the guests would just riff
on them. like a writer's room just tearing stories
apart. And that format, low effort to produce,
high absurdity, turned out to be super durable.
And they basically gave us the mission statement
for that whole vibe in one perfect insane anecdote.
They said something like, if there's a 30 -person
brawl at a Chuck E. Cheese. Oh, yeah. The quote,
it's legendary. In Tampa at a five -year -old's
birthday. Yeah. And it skills into the Burlington
Code Factory parking lot. And ends with someone
defecating in an ex -boyfriend's hatchback. Yeah,
they'll be there to make fun of it. That quote,
it's like, comedic genius in its specificity
perfectly nails their target. Low -stakes crime,
high -level stupidity, people just hurting themselves.
through sheer dumbness. It's the absolute peak
of the dumb people genre. Nailed it. And because
that format was such a hit when Sklarbro Country
wrapped up in 2017, they just transitioned smoothly
into what they're doing now, which is arguably
even bigger, Dumb People Town. Dumb People Town.
Still going strong, twice a week now. Basically
the Sklarbro County model, so Dan Van Kirk, structure's
pretty efficient, right? Get a comedian guest,
talk about their stuff for a bit. Right, keeps
the comedy connection. And then... Dive into
those outrageous news stories. But now they're
mostly sent in by listeners through social media.
Exactly. Which shows their mastery of the modern
media game. They essentially crowdsourced an
infinite supply of content. The listeners find
the absurdity for them and choose the show never
runs dry. And the focus is totally on people
messing up, hurting themselves, doing things
that just make no sense. That low stakes, high
entertainment sweet spot. It's their hallmark
now. They figured out their core skill was dissecting
human stupidity with humor, and they built this
whole self -sustaining podcast universe around
it. It really is a blueprint for how you can
monetize a very specific, critical voice. Okay,
let's switch gears, though. From the weekly grind
to their big, high -concept stand -up specials,
those really prove how committed they are to
integrating their whole brand. All right, moving
beyond the podcast and the sports stuff, we got
to look at their stand -up specials because these
aren't just, you know, stand -up shows. They're
these uniquely framed, high -concept productions
that really lean into their whole brand. They've
done three main specials, right? Two half -hours
for Comedy Central Presents. Yeah, one in 2001,
another in 2009. Those were more standard showcases.
Good stuff, but pretty typical format for the
time. But the one we really need to dig into
is their first hour -long special. What are we
talking about? Netflix, iTunes, 2014. That one.
Yeah. The production wasn't just clever. It was
like total immersion. The ultimate fusion of
their stand -up and their sports commentary careers.
They framed the entire thing like an NFL playoff
game. Recorded it at the Majestic Theater in
Madison, Wisconsin. But it wasn't just like hanging
a few pennants. They went all in. That had to
be expensive, right? High production value. Oh,
absolutely. The commitment to the concept was
total. They basically turned a stand -up taping
into a mock sports broadcast. And the special
had these specific, really targeted cameos from
the sports world. Treating the comedy show like
it was some high stakes game. Think about the
logistics building and running a whole NFL Network
style set for a comedy special. And who did they
get involved? It was some big names, wasn't it?
Significant names. Rich Eisen, anchor for the
NFL Network. He hosted a roundtable discussion.
Analyzing their comedy? Yeah. Analyzing their
jokes with actual NFL players, Dwight Freeney,
Terrell Thomas and the actor Omar Dorsey, who
has a football background. That's wild. It creates
this amazing meta commentary, right? They weren't
just bringing sports guys on. They were having
these serious analysts apply that over the top
sports rhetoric to like. joke construction. Plus,
they had sideline reporter Bonnie Bernstein doing
pre - and post -show interviews with the brothers.
The whole special had a pre -game show, halftime
report, post -game analysis, featuring this very
specific, recognizable sportscast. That level
of concept, that framing, you just don't see
that in stand -up specials. It's totally unique.
It guaranteed the special wasn't just about their
jokes. It was about their entire brand. Cemented
them as the voices where sports and comedy meet.
Absolutely. Now, OK, sharp turn here just to
show the incredible range they have. We need
to talk about their time on the History Channel
and then that really unexpected NPR piece. 2012,
they hosted United States of America on History.
Right. The by the numbers show mixed stats about
the U .S. with stunts and comedy bits that required
a different gear. Right. More informational host
than just comedian. Totally. They had to be factual,
engaging, but still funny. And yeah, it only
ran one season, went on indefinite hiatus, but
it showed they could handle that host role, mixing
smarts, timing, and genuine curiosity. Skills
you need outside pure comedy. But then the NPR
thing, This American Life, that feels like the
most unexpected, maybe the most vulnerable thing
they've done. Definitely the opposite end of
the spectrum from Dumb People Town or Cheap Seats.
This was serious audio journalism. The episode
was called Sklarcross Brothers, and it was about
this deeply personal, lifelong family mystery.
Which was? A rumor, a suspicion, really, that
had apparently persisted in their family forever,
that their mother might have accidentally switched
their identities when they were babies. Whoa.
Okay, wait. Going from jokes about sports gloopers
to investigating whether your mom mixed you up
at birth on NPR, that's a huge tonal shift. How
risky was that for their brand? What did that
prove? Massive risk, yeah. But it paid off because
it showed their storytelling was authentic. They
were willing to put the fundamental question
of their own identity out there for a compelling
story. Showed they weren't just joke machines.
They were like... genuine explorers of the human
condition, even when it involved their own mom
maybe messing up big time. And they actually
found an answer, scientifically. They did. They
hunted down the records, got an expert to compare
their actual baby footprints from the hospital
with their adult feet. Yeah. And the verdict
was, no mix -up. They were who they thought they
were. It's this really sweet, very specific piece
of audio that confirms their place and just adds
this whole other dimension to what they do. Amazing
story. OK, one last thing just to round out the
picture of them trying basically everything.
Their brief dip into reality TV competition.
2021, they auditioned for America's Got Talent.
Season 16. Have that go. Well, their comedy act
got them through the first audition round, proved
they could still win over even tough judges like
Simon Cowell, probably. But they didn't get invited
back for the quarterfinals. Still, just showing
up there. It shows that consistent willingness
to put their act, their brand, in front of literally
anyone, even the most mainstream, sometimes challenging
audience. Okay, so zooming out now, looking at
the whole career, the whole model, it's clear
they weren't just... The twin guys, right? They
had serious writing chops, individual acting
range. They proved they could do more than just
play identical characters. Oh, absolutely. And
we need to really acknowledge their writing skill
and how early they jumped on digital stuff. They
co -wrote with Nick Kroll. Way back. And those
two Streamy award -winning web series are really
important context. Back on Tops, produced by
Michael Eisner's company, Voo Guru, won multiple
Streamys. Back then, early 2010s, that showed
they were succeeding in web video way before
podcasting blew up for everyone. Signal that
adaptability years ahead of the curve. They also
wrote that series, Held Up, starring Caitlin
Olsen. That digital success proves they were
always looking for the next platform. But the
acting roles, too, they show they can work separately.
Jason was on Curb Your Enthusiasm solo, right?
Yeah. Yep. And beyond that, they've got credits
together and apart all over the place. CSI, Law
& Order, Entourage. And maybe most memorably,
they were the DJs in that classic It's Always
Sunny in Philadelphia episode. The gang dances
their asses off. Oh, yeah. They were great in
that. They're just reliable, versatile character
actors. They can land a joke perfectly, whether
they're working together or on their own. And
their legacy, it's also captured on albums, right?
A pretty decent discography that tracks their
stand -up over the years. Yeah, that catalog
shows their longevity, their consistent output.
It goes from Poppin' the Hood. back in 2004 then
slar maps in 07 henderson's and daughters in
2011 then the big one what are we talking about
in 2014 and the most recent one hipster ghosts
in 2018. That steady output feeds their touring,
shows that underneath all the media hopping,
there's still that traditional stand -up work
ethic driving things. And shifting to a couple
of personal details, which often find their way
into the comedy, right? Both married to kids
each, and their spouses are pretty accomplished
too. Yeah, Randy's married to Amy Sklar. She's
a well -known interior designer, was on HGTV's
Design Star. And Jason's married to Jessica Zucker.
She's a fertility therapist who got a lot of
recognition for creating these really sensitive,
much... knitted pregnancy loss cards. So those
personal lives, they provide this endless source
of rich material about marriage, parenting, just
modern life, which then gets filtered through
their unique comedic perspective. Keeps the observational
stuff fresh, grounded in real experience. Okay,
let's wrap this section with two specific anecdotes
that just perfectly capture their, like, meta
-awareness and their absolute willingness to
throw even their own family under the comedic
bus. Ah, okay. First, that prophetic, totally
self -aware moment on After Midnight in 2025.
This just shows how they're always thinking about
how information works now. Jason Sklar said on
the show something like, the way chat GPT is
being used, unchecked, it's going to be the end
of Wikipedia. Okay, bold claim. But the punchline?
The punchline, the... perfect Sklar moment was
him realizing, as he said it, that that very
statement, his prediction would immediately,
ironically, end up on Wikipedia itself being
debated. That's brilliant. The media feedback
loop in action. Exactly. Commentary becoming
the news itself just captures the speed and absurdity
of digital info today. And speaking of unforgettable
information and maybe the most brutal moment
in their recorded history. We have to talk about
the legendary Mother's Day episode of At Midnight.
Oh, God. This one. They brought their mom, Annette,
on the show. Put her right in the hot seat. Yep.
And she was asked, point blank, on national television,
pick your favorite son, Randy or Jason. No. Yes.
And the sources, the clips, they're very clear.
Annette, their mom, chose Randy. And apparently
did it without any hesitation. Just boom, Randy,
brutal, hilariously honest, totally unscripted
maternal preference broadcast to the world. It
perfectly shows how far they'll go mining, even
potentially painful family dynamics for a laugh.
That really does kind of sum it all up. Okay.
So bring it all together. Yeah, their contribution
really is creating this model for how to have
a long, resilient career. They successfully took
their unique twin thing, their sharp wit, that
very specific blend of sports love and high energy
comedy, and they just translated it across every
new media platform that came along. Cable TV,
web series, now the whole podcast universe. They
found that unique voice, that niche, and just
stuck to it, whether they were riffing on like
an old wrestling clip from the 80s or some dumb
celebrity tweet. from yesterday? Totally. Their
blueprint is all about jumping on new things
early, keeping the brand consistent and strategically
using that twin identity. So what does this all
mean for you listening? The Sklar brothers really
show that having that signature, that super -defined
niche, whether it's using an NFL pregame show
for your comedy special or dedicating a hit podcast
to laughing at dumb people's stories, that is
absolutely key. Key to standing out, key to staying
relevant when the media landscape is so incredibly
crowded. They built this recognizable, sustainable,
adaptable brand around what they were passionate
about. And the work, the deals, the loyal audience,
it all followed from that. So let's leave you
with this. Thinking about Jason's comment, his
very self -aware take on ChatGPT and the future
of information, consider this, their current
podcast, Dumb People Town. It thrives on listeners'
stories, right? Real -world human stupidity,
human absurdity. It's fueled by genuine human
folly. What happens to a format like that if,
or maybe when, AI starts generating perfectly
dumb, but... Totally plausible behavior. Fake
news reports, fake crime blotters, fake stupid
action for them to riff on. Will that irreplaceable
human element, that genuine unpredictable spark
of real stupidity, always be funnier, always
win out over the digital simulation? Or could
the lines blur? Something for you to mull over.
Thanks for taking this deep dive with us.