Welcome to the Deep Dive. Today we're looking
at a career that, well, it almost feels like
two different careers, doesn't it? It really
does. We're talking about Robert John Odenkirk.
Right. And it's this incredible contradiction.
You've got the guy most people probably know
now, the intense, dramatic actor from Breaking
Bad from Better Call Saul. The antihero. Yeah.
A major dramatic star who, you know, kind of
came into that later in his career, like in his
late 40s. But before any of that, he'd already
carved out this whole other identity, a really
significant one, actually. A cult comedy legend,
a writer, Emmy winner. It's wild. Absolutely.
Two primetime Emmys for writing comedy back in
the early 90s. That's the foundation. But then
you look at the acting nods later on. Six Emmy
nominations just for lead actor in Better Call
Saul. Six. Yeah. And that's not even counting
the Golden Globes. The Critics' Choice wins.
Right. Three wins there for best actors. The
contrast is stark. So that's our mission today.
We want to dig into that shift. How does someone
go from feeling, as he apparently did, kind of
uncertain about his comedy writing, to becoming
this celebrated dramatic force. And then, you
know, an action star. Yeah, the action star thing
is another curveball. It's a story about restlessness,
I think. About always pushing, adapting. So we're
tracing that path from the weirdness of Mr. Show
to the prestige world of AMC drama. Let's start
at the beginning then. Where did this drive come
from? Well, like a lot of comedians, maybe, it
starts with wanting to get away from somewhere.
Okay. So, born in Berwyn, Illinois, 1962, but
he grew up mostly in Naperville. In Naperville.
Let's just say he wasn't a fan. He's been pretty
blunt about it. Said he grew up hating the place.
Hating it. Wow. Yeah. Called it a dead end. Felt
like there was no culture, nothing creative happening.
He just couldn't wait to get out, move to a city,
be around people making things. That seems like
a big early motivator. And it sounds like home
life wasn't exactly stable either. He was one
of seven kids. Second oldest of seven, yeah.
His parents were Walter, who ran a printing business,
and Barbara. Catholic background, German and
Irish roots. But his father's alcoholism was
a major issue. It led to his parents divorcing.
And Odenkirk's description of his father is.
Well, it's harsh, remote, fucked up and not around.
It was rough. And that had a direct impact on
him personally. Definitely. He made a conscious
choice to avoid alcohol himself because of it.
And you kind of wonder, don't you, if maybe that
experience, that lack of control at home fueled
this intense focus on his work later, like creating
order in his career. Interesting point. That
focus definitely shows up early academically.
You finished high school super young, right?
At 16. Graduated from Naperville North. Said
he was just tired of high school. and impatient,
you know, ready for the next thing. So college
wasn't exactly a straight line either. Not really.
He bounced around a bit. College of DuPage, then
Marquette University in Milwaukee, then transferred
downstate to Southern Illinois University in
Carbondale. That's where he eventually got his
communications BA in 84. But the real action
was happening outside the lecture halls. Oh,
for sure. Especially at SIU. He got heavily involved
with the campus radio station, WIDB. That's where
he really started writing sketches, performing
them. On the radio. Yeah. He created this late
night show called The Primetime Special, ran
from midnight to 4 a .m. Talk about dedication.
That was his first real creative outlet, honing
those skills. So after college, it had to be
Chicago, right? The comedy mecca. Absolutely.
He knew that's where he needed to be. He actually
finished up some college credits at Columbia
College Chicago while diving headfirst into the
improv scene. And this is where he connects with
some key figures. Huge ones. He studied under
the legendary Del Close at the Players Workshop.
Del Close. We should probably pause on that name
for a second. Why? Because his influence, especially
on the kind of comedy Odenkirk would later champion.
He is massive. Totally. Close wasn't just teaching
improv games. He was teaching a philosophy. Long
form improv, the herald, this very structured,
almost intellectual way of building comedy scenes.
Themes, patterns, taking the audience somewhere
unexpected. You can really see the DNA of Mr.
Show in that description. Exactly. That's structured
chaos. And it was at Players Workshop he met
Robert Smigel. Another huge connection. Then
he performed at ImprovOlympic, rubbing shoulders
with guys like Chris Farley, Tim Meadows. Wow.
So he was right in the thick of that incredible
90s Chicago comedy explosion. Steeped in it.
And his own influences kind of point to that
blend of smart and silly. Monty Python's Flying
Circus was his number one. He loved that mix
of cerebral humor and just, you know, laugh out
loud absurdity. What else? You mentioned local
Chicago radio guy Steve Dahl, SCTV, of course,
Steve Martin. Also more niche stuff like The
Credibility Gap, Bob and Ray. It wasn't about
traditional stand -up jokes for him. It was about
constructed weirdness, maybe even anti -humor
sometimes. So by the time he gets the call for
SNL, he's got this really unique... toolkit.
The structure from Del Close, the Python absurdity,
and this like... intense personal drive yeah
all forged in that desire to escape naperville
and find his voice he was ready for the big leagues
or so he thought okay so 1987 he lands the dream
job for a comedy writer saturday night live stays
till 91 he's in the room with smigel with conor
o 'brien i mean that's legendary it absolutely
is but here's where that odin kirk restlessness
that friction really starts to show because even
though he's there at the pinnacle he apparently
felt Really unsure. Unsure about his writing.
Yeah. He's talked about feeling like his stuff
just wasn't quite working at SNL. His style,
more conceptual, sometimes kind of dark or just
plain weird. It didn't always fit the four minute
punchline driven network sketch format. That
makes sense. SNL needs things to land quickly,
often relying on recurring bits or impressions.
Yeah. His Chicago improv background was probably
geared towards something. Longer. Stranger. Exactly.
He felt kind of stifled by the process, the politics
of getting a sketch on air. It wasn't a perfect
fit for his sensibility. And ironically, his
biggest hit for SNL came when he wasn't even
in the building, right? Right. It was during
a summer break. He was back in Chicago doing
a show at Second City called Flag Burning, permitted
in lobby only. Kitchy title. Isn't it? And that's
where he cooked up. Matt Foley, motivational
speaker. For Chris Farley. Specifically for Farley.
Tailored it completely to Farley's physical genius
and that, you know, underlying sweetness he had.
Living in a van down by the river. Iconic. Instantly.
And it worked because I had that classic Odenkirk
mix. The completely over the top, destructive
character. But then that one heartbreakingly
specific, pathetic detail is brilliant. But still,
he wasn't really getting on screen much himself.
Just that one commercial. Pretty much. That Bad
Idea Jeans parody in 1990 was his most visible
moment as a performer there. So by 91, even though
he's surrounded by future megastars, Sandler,
Spade, Rock, Farley were all there. In his last
year, he decides to leave. Yeah. He realized
he didn't just want to write the weird stuff.
He wanted to be the weird stuff. He needed to
perform. And SNL wasn't really offering him that
shot. Which leads him to another legendary, albeit
short -lived, show. The Ben Stiller Show, 1992.
He'd known Stiller briefly from sharing an office
at SNL. Ben hired him as both a writer and a
performer this time on Fox. And this show, again,
critically adored, commercially. Not so much.
Classic story, right? They created some amazing,
bizarre sketch. I remember Manson Lassie. Oh
my God, yes. And the show won an Emmy for outstanding
writing. He was already canceled by the time
they got the award. Exactly. It just proved the
network still didn't quite know what to make
of that specific brand of smart alternative comedy.
So after Stiller ended, he did a stint writing
for Conan. Yeah, late night with Conan O 'Brien,
93 to 94. Solid writing gig, kept him working.
But the real game changer was teaming up with
someone he met on The Stiller Show. David Cross.
David Cross. And that brings us to the monument,
really. Mr. Show with Bob and David. HBO, 1995
to 1998. This show is... It felt different. Not
just the content, but the whole structure. Totally
revolutionary for a TV sketch comedy. Like we
talked about with Double O's, it wasn't just
isolated bits. Sketches flowed into each other,
bled together, commented on each other. It was
dense, non -linear meta. You kind of had to pay
attention, right? It wasn't background noise
comedy. Definitely not. And the talent it fostered?
Unbelievable. Sarah Silverman, Jack Black, Paul
F. Tompkins, Tom Kenny, Brian Posen. The list
is insane. Critically loved, Emmy nominated,
but because it was on HBO back then. The audience
was smaller, yeah. But super dedicated. That's
the cult status thing. Its influence hugely outweighed
its ratings. It became this touchstone for comedians
and writers. But when they tried to take that
Mr. Show vibe to the big screen, it didn't go
well. Oof, yeah. Run, Ronnie, run in 2002 based
on a Mr. Show sketch. But the studio took over
the edit and Bob and David basically washed their
hands of the final version. That must have been
painful, losing control like that. Crucial moment,
I think. It seems like it really pushed Odenkirk
towards wanting more control, wanting to direct
his own stuff, which unfortunately led to a pretty
tough decade for him behind the camera. Right,
the 2000s. People forget this period, but he
was directing features. He was. And his first
one, Melvin Goes to Dinner in 2003, was actually
well -received. Small, indie, character -focused.
Won an audience award at South by Southwest.
Showed he could handle nuanced stuff. But then
came the studio comedies. Yeah. Let's go to prison
in 2006. The Brother Solomon in 2007. Those did
not go over well. Critically panned, commercially
unsuccessful. It feels like maybe the studio
system just wasn't the right fit for his sensibility,
especially after the run, Ronnie, run experience.
He needed that creative freedom. Seems likely.
And he was trying constantly to get his own stuff
made, too. Develop TV pilots like The Big Wide
World of Carl Lamke, David's Situation. But nothing
got ticked up. It sounds like a really frustrating
time. Lots of work, not a lot clicking commercially.
But even while his own projects were maybe struggling,
he was still finding and championing other unique
voices, right? Absolutely. This is key. He didn't
abandon that alt -comedy world. He famously discovered
Tim Heidecker and Eric Wareheim. Tim and Eric.
Yeah. He helped them get... Tom goes to the mayor
and then Tim and Eric. Awesome show. Great job
off the ground. He saw their bizarre genius and
used his clout to support it. It shows he was
still connected to that fringe, even when trying
to make more mainstream stuff himself. And we
have to mention the big what if from this era,
The Office. Ah, yes. The Michael Scott near miss.
He was seriously in the running for the pilot.
Can you imagine? It's hard to picture anyone
but Carell now. It really is. But clearly the
office folks loved him because they brought him
back for a guest spot in the final season. He
played this manager in Philly who was very Michael
Scott -esque. A fun little nod to that alternate
reality. But his real path, the one nobody saw
coming, was about to open up. Not in comedy,
but in drama. Yeah. Albuquerque was calling.
Okay, so 2009, Breaking Bad is on AMC, already
a critical darling, and suddenly Bob Odenkirk
shows up. Out of nowhere, right, as Saul Goodman,
the flashy, morally flexible lawyer. And the
crazy thing is, this wasn't supposed to be a
big deal initially. Not at all. Get this. The
role was written as just a three -episode guest
spot in season two. Three episodes? Seriously?
Yeah, he was just meant to be a plot device,
basically. Help Walt and Jesse navigate some
legal trouble. But Odekirk just popped. He really
did. That mix of sleaze and confidence, comedy,
and, like, genuine menace underneath. Vince Gilligan
and Peter Gold, the creators, saw it immediately.
They were blown away. That three -episode arc,
forget it. He became a series regular from season
three all the way to the end. He just brought
this unexpected depth to the character. And that
depth, that complexity they saw. That led directly
to Better Call Saul. The spinoff premiered 2015,
ran till 2022. And now Odenkirk isn't just a
scene stealer. He's the lead. Charting that whole
transformation of Jimmy McGill into Saul Goodman.
And he's a producer on this one, too. Huge shift
from cult comedian to the face of a major prestige
drama. And the acclaim. It was intense. Off the
charts. I mean, the Emmy situation alone is kind
of nuts. Six nominations for Outstanding Lead
Actor in a Drama Series for Saul. Six times,
and he never won that specific Emmy. Right. It
ties the record for most nominations in that
category without a win, which is, you know, a
weird record to hold, but it speaks volumes about
how consistently great the critics thought he
was year after year. And the Golden Globes piled
up, too? Five nominations there. But he did get
the win multiple times at the Critics' Choice
Awards. Right, three wins for... Best actor in
a drama series. Yeah. 2015, 2016, and for the
final season in 2022. So the critics at least
were definitely validating this dramatic transformation.
Absolutely. But here's what I find fascinating.
Even while he's plumbing the depths of Jimmy
McGill's tragic soul. He can't quite quit the
comedy. Exactly. Right in the middle of the Saul
run. 2015, he gets back together with David Cross
for W. Bob and David on Netflix. All new sketch
series. Yeah, he co -created it, wrote, starred,
produced. It's like he needed that outlet, a
palate cleanser from all the drama, maybe. Get
back to the absurdity. Maintain the balance.
Seems like it. And at the same time, his dramatic
success was opening doors in movies, big time.
Yeah, suddenly he's popping up in really respected
films. Supporting roles, but in quality projects.
Spectacular. Now, he did voice work in Incredibles
2. Ben Bradley's Deputy in the Post showed up
in Greta Gerwig's Little Women. And Nebraska,
the Alexander Payne film. Yeah. That felt significant.
Huge. 2013, beautiful black and white film, nominated
for the Palme d 'Or at Cannes. That wasn't just
a small part. It really cemented him as a serious
actor who could hold his own in high -level independent
cinema. He proved he had the dramatic chops,
no question. So, okay. We've got the cult comedy
writer, the prestige drama lead. You'd think
maybe he'd settle into that groove, right? You
would think. But nope. The next pivot is maybe
the most unexpected of all. He becomes an action
hero in his late 50s. It sounds completely bizarre
on paper. Bob Odenkirk doing fight choreography.
But then nobody comes out in 2021. And it works.
He plays Hutch Mansell, the seemingly boring
suburban dad who turns out to have a very particular
set of skills. A very violent past, yeah. And
apparently he didn't phone it in. The training
was intense. Get this, two years. He trained
for two years to do a lot of the stunt work and
fighting himself. That's serious commitment.
And audiences responded. The movie was a hit.
Number one at the box office when it opened.
Huge success. And remember, he produced this
one too. Through his own company, he had that
control. Cal Gold Pictures, right? He set that
up in 2020. Signed a deal with Sony TV. Smart
move for creative control long term. Definitely.
And the success of... Nobody was so big, they're
already doing a sequel. Nobody 2 is slated for
2025. Incredible. So he's got this action franchise
going, but he's still exploring other things
on TV too. Yeah, he didn't just stick with the
action. In 2023, he starred in Lucky Hank on
AMC, based on a Richard Russo novel, Straight
Man. Playing a character quite different from
Houch Mansell. Totally. A kind of burnt out,
neurotic English professor. Much more internalized,
closer to maybe some of his earlier comedic personas,
but grounded in drama. And then comes this amazing
guest spot that brought everything full circle
almost. The bear. Oh man, that episode. The Christmas
episode. Fishes. Just chaos. And he played Uncle
Lee. And he got an Emmy nomination for it. Outstanding
guest actor in a comedy series. It was brilliant
because unlike Saul, who's loud and performative,
Uncle Lee was all this simmering resentment and
anxiety beneath the surface. Just fantastic acting
within that insane comedic pressure cooker. It
really showed his range yet again. And then just
when you think, okay, what else can he possibly
do? He makes his Broadway debut. In a monster
of a play, no less. David Mamet's Glengarry Glen
Ross. Yeah, in 2025. And not just any part. He
played Shelley the Machine Levine, the desperate,
washed -up salesman. It's a classic, incredibly
demanding, dramatic role. Echoes of Jimmy McGill's
desperation, maybe, but in a totally different
theatrical context. Absolutely. And he nailed
it. The reviews for his performance were stellar,
even if the overall production got mixed reactions.
He earned a Tony Award nomination for Best Featured
Actor in a Play. Wow. a tony nomination the only
nomination the show received actually which really
highlights how much his performance stood out
it just confirmed his status as a heavyweight
dramatic actor stage or screen and throughout
all these acting transformations he kept writing
too never stopped he put out that book of comedy
sketches and essays a load of hooey back in 2014
then the memoir in 2022 comedy comedy comedy
drama i mean the title says it all right perfect
title And then showing yet another side, he co
-wrote a children's poetry book with his daughter,
Erin, called Zealot and Other Important Rhymes.
Came out in 2023. Amazing. The sheer breadth
of it all. Comedy, drama, action, writing, producing,
Broadway, kids books. Yeah. It's just relentless
creativity. So his career has been full of these
incredible, sometimes jarring shifts. But in
2021, life itself threw him a curveball that
was far more serious. Yeah, the health scare
on the set of... better call Saul. That was genuinely
terrifying. He collapsed while filming in Albuquerque,
July 2021. And the initial reports were kind
of vague, but the reality was grim. Extremely
grim. It wasn't just a small heart attack as
sometimes gets reported. It was what they call
a widow maker. Which means? It means a total
blockage of the main artery supplying blood to
the heart, the LAD. It's often fatal if not treated
immediately. He'd actually been diagnosed with
some plaque buildup back in 2018, but this event
was catastrophic. His heart actually stopped.
Completely stopped. He needed CPR onset, multiple
defibrillator shocks to get his pulse back. It's
hard to overstate how close he came. Wow. And
the impact on the show itself could have been
huge. Oh, absolutely. Peter Gold, the showrunner,
said very clearly afterwards that if Odenkirk
hadn't pulled through, that would have been it
for Better Call Saul. They wouldn't have recast,
wouldn't have tried to finish it without him.
That says a lot about his importance to that
entire project and the loyalty there. It really
does. Incredible loyalty. Thankfully, he made
a remarkable recovery and was back on set by
September to finish the final season. Just amazing
resilience. Switching gears a bit, his family
life seems pretty grounded amidst all the career
chaos. Married Naomi Yelmtoff in 97. Right. And
she's in the business, too. She was an executive
producer on W. Bob and David. They have two kids
together. And his brother, Bill Odenkirk, is
also a successful comedy writer. The Simpsons,
Futurama. It's definitely a talented family.
Runs in the blood, apparently, which actually
leads us to maybe the most surprising discovery
about his background. Oh, yeah, the Finding Your
Roots episode. This was wild. Totally unexpected.
So the guy who hated suburban Naperville and
defined himself through edgy, anti -establishment
comedy, turns out he has royal blood. Seriously.
Royal! Well, descended from royalty, he learned
he's related, through an illegitimate son, to
Frederick Charles, who was the Duke of Schleswig
-Holstein -Sonderburg plan back in the day. Okay,
so what does that actually mean in terms of,
like... current royal. Yet this. It makes him
an 11th cousin to King Charles III. No way. Bob
Odenkirk and King Charles are cousins. That's
hilarious. Isn't it? The irony is just perfect.
The ultimate outsider comedian discovers this
aristocratic connection. Amazing. And wasn't
there some other interesting ancestor? Like a
soldier. Yeah. Another surprise. He had an ancestor
named Jean -Jacques Fricker who fought for Napoleon.
A French soldier at the Battle of Aspern -Essling
during the Napoleonic Wars. Just adds another
layer of unexpected history to the guy. From
neighbor. to Napoleonic battles and German Dukes.
Quite a family tree. You could say that. And
finally, capping off this whole incredible journey,
he got his star on the Hollywood Walk of Fame.
Well deserved. When was that? April 18th, 2022.
They timed it perfectly for the premiere date
of the final season of Better Call Saul. Nice
touch. And where is it located? Even better touch.
It's right next to Bryan Cranston's star. Ah,
perfect. Walt and Saul side by side on Hollywood
Boulevard. That feels right. Hashtag tag outro.
So when you step back and look at the whole picture,
it's kind of staggering, isn't it? From writing
Matt Foley at Second City, feeling unsure at
SNL, creating the cult chaos of Mr. Show. Through
the directing struggles, then the complete reinvention
as Saul Goodman, becoming this acclaimed dramatic
actor. Then pivoting again to become a bona fide
action star in his late 50s, getting a Tony nomination
on Broadway. It's a career defined. By refusing
to be pinned down. By perseverance, sure, but
also by this incredible adaptability. He just
never settled. Which brings us to our final thought
for you, the listener. After hitting these peaks,
prestige drama, action stardom, Broadway acclaim,
what's the next unexpected turn for Bob Odenkirk?
You might think maybe a quiet indie drama. Or
producing more. Nope. Get ready to this. His
next big starring role. is playing Johnny in
the Room Returns. Yes, you heard that right.
A reportedly shot -for -shot remake of Tommy
Wiseau's legendary 2003 disaster piece, The Room.
I mean, it's just perfect, isn't it? After scaling
the heights of serious artistic achievement,
he dives right back into the glorious, absurd
muck of cult infamy. It proves that the Mr. Show
spirit, that love for the brilliantly bizarre
and the embrace of failure as art, that's still
fundamentally who he is as a performer and creator.
He just keeps defying categorization, keeps surprising
us. An incredible arc and probably far from over.
Absolutely. Well, that's our deep dive on Bob
Odenkirk. Thanks for joining us. We'll catch
you next time.