Welcome back to the deep dive Okay, so today
we're turning our attention to One of comedy's
most let's say candid chaotic and definitely
complex figures Robert Youngly jr. But you know,
everyone just knows him as Bobby Lee. Yeah, absolutely
and if you like if you've been following his
career at all. I mean, the evolution is incredible,
isn't it? From that Seminon sketch comedy stuff
to basically being a founding father of the Modern
Video Podcast, his story's got so much more texture
than just the highlights. Totally. And that's
our mission today, really. We want to synthesize
the journey, the personal and professional stuff
that's documented in the source materials we've
looked at. We're going to trace his path from
his San Diego roots, that really tough youth.
right up to now, where he's a foundational figure
in sketch comedy, sure, but also this pioneer
in independent digital media. And what's really
striking, I think, is that duality you mentioned.
We're not just taking off career milestones.
We have to look at the personal resilience that's
right there alongside it all, documented step
by step, almost. Yeah, it's inseparable. OK,
so let's kick off with the vitals just to set
the scene. Born September. 17th, 1971, San Diego,
California. And his work, I mean, it spans standup,
film, TV, and of course, podcasting. And the
comedy itself is pretty broad. You've got observational
stuff, yeah. But he often goes into black comedy,
blue comedy, tackling really sensitive things
head on. Like what kind of things? Well, human
sexuality, American politics, gender differences.
just basic human behavior, but with this, like
raw candor. And that candor, that's really what
defines where he is now, right? He's co -hosting
Bad Friends with Andrew Santino, which is massive,
started in 2020. Huge. And then there's the earlier
one, Tiger Belly, which is so culturally significant,
he co -hosted that with Kaleo Lacoon. These two
shows, they're kind of the peak of that big entrepreneurial
shift he made. But that shift, I mean, it took
decades to get there. And the resilience, like
you said, it really starts way back in his childhood,
which kind of brings us to section one, right?
That really unconventional. path he took towards
comedy. OK, yeah, let's dive into that. Starting
in Poway, California, that's where he grew up
with his younger brother, Steve, parents were
Korean immigrants, Jeannie and Robert Lee. Right.
And the sources mentioned the local schools he
went to, Painted Rock, Twin Peaks, Poway High.
But the crucial context here, I think, is the
family environment. It was all about hard work
owning their own business. His parents had clothing
stores and Escondido and Encinitas. And that
detail, it feels really pivotal because, you
know, being the eldest son in an immigrant family
with small businesses, there's often this really
strong. maybe unspoken expectation that you'll
join the family business eventually take over.
Exactly. So that sets up this immediate, like,
fundamental conflict when he decides to go down
this totally unstable path of comedy instead.
Right. Such a different world. Yeah. But even
before comedy, there was this little hint of
performance. The sources mentioned he was on
a breakdancing team in high school. Oh, really?
Breakdancing? Yeah, so it shows maybe an early
lean towards being on stage, physical performance,
even if nobody saw it as like a career path back
then. After high school, he did briefly go to
Palomar College, but well, that didn't last long
before this big turning point. OK, here we go.
This is where fate or maybe just circumstance
takes a really sharp turn. The Stand Up Origin
story, 1994. It wasn't like he planned it meticulously.
It sounds almost accidental. Totally accidental.
He was working in a coffee shop slash restaurant.
And the sources say it just closed down abruptly.
He needed work. So he literally just walked next
door. And what was next door? Let me guess. The
Comedy Store. The Comedy Store in San Diego.
Yeah. He started working there just doing odd
jobs for a few months. Wow. Just being there,
proximity. Right. That's going to be the biggest
ingredient sometimes in comedy, just being in
the environment. Absolutely. And because he was
there, he eventually plucked up the courage,
got on stage during a amateur night. And that
first set, apparently, that was it. That was
the spark. And things moved fast after that,
didn't they? Unbelievably fast. The sources show,
like, within just one year, he's getting offers
to open for pretty big names at the time, Pauly
Shore, Carlos Mencia. Wow. And that success immediately
led to him working regularly at the main comedy
store, the legendary one in LA. So hang on. In
about a year, he goes from working odd jobs next
to a defunct coffee shop to being a regular feature
at the comedy store in LA. That's meteoric. It
really is. That kind of speed you'd think would
bring instant validation, right? But actually,
it seems like it kind of made the distance with
his family even bigger. Which brings us to that
whole parental support thing, or lack thereof,
initially. Yeah, and Lee's been super open about
this, about that initial conflict. His parents,
you know, they had those traditional values,
the hopes tied up with the family business. Yeah.
They were distinctly unsupportive at first. He
talked about it pretty bluntly, didn't he? Said
something like, for the first few years of his
career, this time when he's actually killing
it professionally, his parents barely spoke to
him. Yeah. Can you imagine that? Achieving this
dream, but feeling totally isolated from your
family. Brutal. But the turning point, the story
about that, it's such a perfect kind of poignant
illustration of the gap they were dealing with,
culturally and vocationally. The reconciliation
apparently kicked off after he was on The Tonight
Show with Jay Leno. Right. The legendary phone
call from his dad. Exactly. His father calls
him up, but not to say great job or anything.
No, he asks how much Bobby had to pay to get
on the show. Which just cuts right to the bone,
doesn't it? That immigrant mindset, maybe? that
success in this baffling industry like Hollywood,
it must be about money, not talent. They just
couldn't wrap their heads around being a comedian
as a real job. It's not lack of love. Maybe just
no frame of reference, like you said. But the
sources do say that after that appearance, his
dad did apologize, said sorry for not supporting
the comedy thing before. That was like the first
big step, you know, healing that divide. And
that healing eventually led to actual family
collaboration later on, which is pretty cool.
Shows they bridge that gap somehow. His younger
brother, Steve, started showing up in non -speaking
roles on MATV. Mm -hmm. And his whole immediate
family was even in one specific sketch on the
show. Wow. And then, get this, in 2007, showing
how far things had come, he actually pitched
a sitcom to Comedy Central. The idea was it'd
be about a Korean family starring his own family.
No way. That's incredible. From barely speaking
to pitching a sitcom together, that's quite a
journey for them. It really is a total transformation.
Okay, so the family starts coming around, even
gets involved, and that timeline takes us right
into the next big phase for him professionally.
sketch comedy, and making that move into acting.
Yeah, and obviously, that phase is just dominated
by MADTV. He joined the cast in 2001, and that
was, like, instantly groundbreaking. The sources
are clear. He was the show's first and only Asian
cast member during his entire run. Which meant
huge visibility, obviously, but also... Man,
the pressure. Immense pressure. Being the only
one, especially back then, early 2000s sketch
comedy, that often meant getting pushed in the
roles that relied pretty heavily on stereotypes
for the joke. And this is something the sources
really bring out, highlighting his own internal
conflict with it. He got famous doing these characters,
but he's openly talked about dreading certain
roles. Yeah, I remember reading that. He specifically
mentioned playing based on Connie Chung. And
those average Asian skits. Right. Which, I mean,
talk about a psychological burden. You're getting
success, right? Job security, fame, people recognize
you. Yeah. But the price is playing characters
that maybe undermine or at least lean into the
very stereotypes you and your community are fighting
against. Yeah. Especially tough for a comedian
whose later work, like we'll get to, is all about
exploring Asian American identity with way more
nuance. That MADTV era must have been artistically
kind of agonizing at times. Must have been. Yeah.
Despite that he stayed for so long that says
a lot about his talent his commitment. Maybe
just his professional grit Totally. He was a
core part of that cast until the show got canceled
in 2009. That's an eight -year run, solid. And
he even came back for that brief revival on the
CW in 2016. Right. And that stability, that platform
MEBTV gave him, it definitely let him leverage
that visibility into film roles, TV roles, signaling
that shift into being a broader actor, not just
a sketch guy. Okay, let's look at some of those
key roles and film highlights then. He popped
up in that 2004 cult hit, Harold and Kumar go
to White Castle. Oh yeah, Kenneth Park. Kenneth
Park, exactly. And he came back for the sequel
in 2011 too. And you also see him fitting into
other big comedies around that time, right? Like
Pineapple Express in 2008. And Sacha Baron Cohen's
The Dictator in 2012 where he played Mr. Lau.
So he's showing he can move from sketch character
work to being a reliable comedic actor in movies.
But his later TV stuff, it feels like maybe a
deliberate shift, doesn't it, towards more grounded
roles, or at least less, less broad, maybe. He
co -starred in that ABC sitcom, splitting up
together. Yeah, from 2018 to 2019. But I agree.
I think the real measure of his versatility comes
through in some of the recurring characters he
played later, like Jin Ji -won on the Magnum
PI reboot. Right. He was on that for a while,
2019 to 2023. That's a sustained role, kind of
dramatic, kind of comedic, on a network procedural.
pretty different. And then you contrast that
with his role as Dr. Kang on Reservation Dogs
on FX Hulu, which got a lot of claim. Oh yeah,
Dr. Kang was fantastic. So cynical, burned out,
world weary. It was such a nuanced performance.
Exactly. That character, Dr. Kang, it really
felt like... like a conscious departure from
the high energy, sometimes stereotypical stuff
from MADTV, it showed he had this dramatic subtlety,
this emotional depth that maybe got a bit lost
in the earlier work. Yeah, definitely. And during
this period, he's also doing these side projects
that, looking back, kind of seemed like they
were preparing him for the digital thing. He
hosted the MusiCare's MAP Fund benefit concert
in 2013. OK. And, critically, back in 2012, he
got hired to reboot Maker Studios' YouTube common...
channel, The Station. Ah, Maker Studios. Right.
That experience put him right in the middle of
that whole emerging world of independent online
content. Early days still, but significant. Totally.
It gave him the blueprint, maybe the foresight,
for what turned out to be his biggest career
pivot yet, which is section three, the podcasting
revolution. He didn't just ride that way. He
kind of helped build the boat. He really did.
And his success there is built on this, like,
dual podcast empire, right? You've got Bad Friends
with Andrew Santino, the huge hit that kicked
off in 2020. Massive. But the real foundation
for his indie media career, you got to say, is
Tiger Belly. Yeah, let's focus on the start of
Tiger Belly. That began earlier, 2015, initially
co -hosted with Kalei Lacoon. And even though
their personal relationship ended in 2022, the
podcast keeps going, which says a lot about their
dedication to that shared creation. It really
does. And the show's important, not just for
the content, but its whole model, its video and
audio, usually like 60, 90 minutes. The sources
point out the team behind it, Gilbert Gallin
on tech, George Kimmel producing. Right. And
even the intro song Shadowgook, which he co -wrote
and performed with Koon. It's just an example
of the really personal, almost provocative ownership
they take. And the content itself. This is why
Tiger Belly feels so revolutionary, especially
if you think back to those NAD TV struggles we
talked about. The conversations are super personal,
yeah, they touch on pop culture, but they often
dig deep into really crucial Asian American issues.
Like what specifically? Things related to the
entertainment industry, adolescents, sexuality,
ethnicity, racism, politics, all sorts of stuff.
So it's like the ultimate reclaiming of his own
narrative powers in it. After spending years
playing roles he apparently dreading, dictated
by network TV, he co -creates a space where he
defines how they talk about Asian -American identity.
It feels like this huge creative, maybe even
emotional relief. Absolutely. But what's interesting
is how it actually started. It wasn't even his
main podcast idea at first, was it? No. He was
apparently working on a totally different pitch
with Eric Griffin for All Things Comedy, but
that kind of fizzled out. Right. Instead, Tiger
Belly sort of grew out of a personal crisis.
Kalei Lacoon was starting a podcast while she
was recovering from heart surgery. Just needed
something to do. Lee was helping her out. Then
he started appearing on it. And that just took
off. It had more momentum than the other idea.
So he shifted his focus completely to doing Tiger
Belly with her. So yeah, this thing, born out
of necessity during recovery, ended up becoming
one of the most influential video podcasts out
there. That's wild. Yeah. But running a show
that's that candid, that open, it means you're
constantly under the microscope, right? Which
brings us to that whole controversy thing, the
Tijuana story that blew up again in 2023. Yeah,
that was rough. Clips resurfaced in April 2023.
Lee recounting this story involving, as he described
it, a young adult prostitute in Tijuana. And
it just ignited this huge online backlash, allegations,
intense criticism about the content itself. And
it really highlights that tricky line, doesn't
it, between dark comedy, shock humor, and how
people perceive it, especially when it's told
like a personal story on a podcast. That feeling
of intimacy makes people. Maybe expect more literal
truth. Exactly. The perceived authenticity is
higher. So Lee had to address it, right? He used
his own platform, Tiger Belly, later that month
to do damage control, basically. And the clarification
was key. He had to come out and say point blank.
The story wasn't true. It was totally made up.
Yeah, he called it a dark joke, said it was pieced
together from a couple of awful bits. The fact
that he had to go on his own show to explain
that a shocking story was fiction. It just shows
how intense that accountability is now in the
digital age. It definitely signals a shift, maybe,
for dark comedy when any clip can be pulled,
stripped of context, and live forever online.
The risk is your joke gets taken as a confession.
For sure. And his quick, direct response kind
of underlines how crucial it is for independent
creators, especially boundary pushers, to actively
manage their own narrative when things go sideways.
And that need to manage your narrative, your
story. It feels even more relevant when we shift
into section four. This is where we get into
the really deep stuff. the personal struggles,
the resilience, and also the interests that kind
of ground him. Yeah, and the absolute anchor
here is the long road to sobriety, which isn't
just one event. It's this really complex journey.
Multiple attempts, relapses, often tied directly
to intense life pressures. And we have to start
by understanding how early this began. The sources
say he started using meth and marijuana around
12 years old. Twelve! And heroin by 15. That's
an incredibly difficult, traumatic start for
anyone, let alone someone heading into the high
-pressure world of comedy. Yeah, that kind of
early substance use, it makes you realize the
career he built later was basically this decade
-long tightrope walk over some serious personal
turmoil. After three different rehab attempts,
he finally got sober at 17. 17. And that first
stretch of sobriety lasted 12 years, which is
huge, especially while navigating the chaos of
breaking into comedy, moving from San Diego to
LA, all that rapid success. Absolutely monumental.
Which makes the story of his first big relapse
even more impactful. It break that 12 -year streak.
He relapsed on Vicodin. And the trigger, according
to the sources, wasn't partying or anything like
that. It was directly tied to his work. He got
negative feedback from a producer. Wow. That
detail says so much about the psychological toll
of that industry, doesn't it? It wasn't a personal
failure. It was professional rejection. or at
least perceive rejection, that cracked this decade
-plus sobriety. It really shows how tied up his
self -worth must have been in that external validation
back then. Yeah, the pressure cooker of TV production.
Rejection hits hard, and self -medication becomes
the coping mechanism. But the sources also document
the flip side, the second chance. His sobriety
getting another boost, again tied to the industry,
but this time through support. Right, this is
a story he told on Comedy Central's. This is
not happening, yeah. He got sober again after
a MAD TV producer, Lauren Dombrowski, really
went to bat for him. This was after he'd apparently
been fired from the show for a second time. Imagine
that. In an industry known for being pretty cutthroat,
someone believes in you enough to advocate for
you, give you that second chance. That moment
of mentorship likely saved his career, maybe
more. But the journey, as they say, it's never
really linear, is it? He admitted later on Tiger
Belly episode 224 that he'd relapsed again. Yeah,
much later in life. And this time, the trigger
was even more profound. The death of his father
in August 2019, his dad passed away from Parkinson's.
So that later relapse tied to grief, it just
further humanizes the whole struggle, you know,
shows that recovery is this ongoing thing, vulnerable
to life's biggest hits, like losing a parent.
After that, he went back to rehab, got sober
again, and he stayed open about it, identifies
as a recovering alcoholic. and that repeated
ability to use his own platforms, like Tiger
Belly, to talk about these wrong moments, vulnerability,
addiction, recovery, it almost transforms his
personal battle into something shared, something
communal. It's an act of service, maybe, but
also just incredibly resilient self -documentation.
Definitely. OK, turning briefly to relationships
and family connections, we mentioned his 10 -year
relationship with Kalyla Kuhn, his Tiger Belly
co -host, ended in 2022. The fact that they decided
to keep co -hosting their very successful show
after breaking up, which is pretty remarkable,
shows a real prioritizing of the creative partnership.
Yeah, over the personal friction, which can't
be easy. And his younger brother, Steve Lee,
he's still around, active in media too, musician,
podcaster, comedian himself. Still an important
part of his world, creatively and personally.
Right. And finally, just to round things out,
we should touch on his personal interests and
hobbies, because they offer this necessary contrast
to all the intense professional demands we've
been talking about. He's apparently a huge, long
-time supporter of Arsenal Football Club. Ah,
a gooner, okay. Yep, and also a really avid fan
of video games, especially the long, immersive
ones. He often talks about stuff like FIFA, Stardew
Valley, The Elder Scrolls, Red Dead Redemption
2, The Witcher series. You know, when you think
about the kind of work he does, The constant
public vulnerability, the energy needed for two
big podcasts, touring stress, these hobbies make
a lot of sense, don't they? Whether it's the
focused distraction of watching football or just
getting lost in these huge narrative RPGs like
Witcher or Red Dead, it probably serves this
crucial psychological need. Stability, escapism
from the pressure. Yeah, grounding the chaos
maybe. So, okay, we've covered a lot. This whole
extraordinary zigzagging journey. What does it
all mean when we try to synthesize the documented
evidence for you, the listener? Right. Let's
boil down the key takeaways. First, you just
have to highlight the sheer adaptability across
his career timeline. He starts as a club comic,
becomes a TV sketch stalwart for almost a decade,
and then pulls off this incredible pivot to independent
media, co -founding Tiger Belly in 2015, then
Bad Friends in 2020. That shows such a sharp
understanding of how media was changing. Totally.
And second, that theme of resilience. It's just
unavoidable. The documented evidence of his long,
hard road with sobriety, starting with drug use
at 12, navigating that very specific relapse
triggered by producer feedback, then the grief
relapse after his father's death, doing all that
while staying so public. It just hammers home
that his success was won through these constant
really intense personal battles. Yeah, he basically
spun an accidental job next to a closed coffee
shop into this decades -long career. He navigated
the cultural stuff with his parents, survived
the industry pressures that fueled addiction,
and evolved from, you know, performing roles
he dreaded to be becoming this indie media force
who sets his own terms. It really is the ultimate
story of reclaiming your own narrative, which
I guess leads us perfectly into our final provocative
thought for you to chew on after this deem dive.
Okay, so considering everything we've discussed,
especially those specific struggles documented
early on, like the conflict with his parents
about his career, that internal dread he felt
playing certain racial characters on MED TV,
what does his pivot to hosting Tiger Belly really
signify? Yeah, because Tiger Billy is this platform
he co -created built specifically to talk about
Asian -American issues, sexuality, ethnicity,
racism, all completely on his own terms. Does
creating that kind of long -form, self -controlled,
really intimate media, does it fundamentally
change the game, change the relationship between
the artist and the audience? Is it like a vital
tool now for processing, controlling, and ultimately
maybe mastering your own complex life story?
Something to think about for sure as you appreciate
the layers and the complexity of comedy today.
Thanks for joining us for this deep dive into
the truly resilient life and career of Bobby
Lee. Yeah, we hope you had a deep appreciation
for not just the comedian, but the survivor and
the media entrepreneur behind it all. Until next
time.