Welcome to the Deep Dive. We're here to unpack
the insights from, well, quite a stack of sources,
aiming to get you right up to speed. And our
subject today is... A really fascinating study
in maybe professional camouflage, Benjamin Joseph
Manley Novak. Now for millions, probably billions
globally, he is Ryan Howard. You know, the pimp
from The Office, that symbol of like ambition
and millennial angst. Yeah, Ryan the Tan. And
look, if that's all you know, you're really just
seeing the very tip of the iceberg. Our mission
today, our deep dive is basically to show that
Novak is so much more than just Ryan. We're tracing
this creative path. It's almost unique in Hollywood
today. It really is. Harvard guy, stand -up comic,
award -winning writer for one of the biggest
shows ever. Director, New York Times bestselling
children's author, seriously. And, okay, maybe
a less successful tech entrepreneur, but still.
Right. Okay. So let's unpack that. We've gone
through the sources trying to find the why. Like,
what's the driver behind this constant reinvention?
And it is successful reinvention, mostly. What
actually links... You know, a book of 64 witty
short stories, a kid's book that basically messes
with the reader, and directing a pretty dark,
complex movie. Well, the thread seems to be narrative
storytelling. Okay. Born July 34th, 1979, Newton,
Massachusetts. His career officially starts around
2001, runs to now. It really suggests someone
obsessed with mastering story, but like across
every possible format. Exactly. That's the core
argument, I think. It doesn't feel like a series
of, you know, lucky breaks. It feels more like
he's building this portfolio. And it's all built
on one skill, analyzing and using story structure.
And he's got that rare mix, right? Like super
intellectual, Harvard level rigor, but also this
sharp popular comedy instinct. Absolutely. And
to really get it, you have to go right back.
Right to the beginning. A foundation. Okay, so
that foundation. You mentioned this structural
compulsion. It seems really rooted in his family,
his early education back in Massachusetts. Sounds
like a very literary household. Oh, absolutely.
His parents are Linda and William Novak. And
William Novak, his father, he's a key figure
here. He's an author, sure. But he also co -edited
the big book of Jewish humor. Ah, okay. So right
away, BJ's getting exposed to, like... The academic
side of comedy, not just laughs, but why it's
funny, culture, timing. Precisely. Analyzing
it, understanding the mechanics. But his dad's
work went way beyond that. He was kind of a master
ghostwriter. Right. That's the fascinating part.
He wasn't just writing his own stuff. He was
channeling other people. Huge names. Think about
the sheer variety of voices he had to capture
authentically. We're talking Nancy Reagan. Wow.
Lee Iacocca, the car guy. Magic Johnson. The
basketball icon. Imagine growing up seeing your
dad technically construct these totally different
public personas through writing. Yeah, that teaches
you that writing isn't just like inspiration.
It's a technical skill. You can build a voice,
build a narrative for almost anyone. Exactly.
That skill, that understanding of voice construction.
Invaluable later for creating characters, say,
for The Office. It starts with technical mastery.
Okay. So that's the whole environment. What about
school? Also points to that intellectual rigor.
Solomon Schechter Day School, Brown Middle School.
Camp Rama in New England. But here's the bit
that fans, especially office fans listening,
will love. The high school connection. This is
legendary, right? It really is. Newton South
High School. He graduates in 97. And guess who's
in his class working on creative stuff with him?
Gotta be John Krasinski. Jim Halpert himself.
Bingo. Future Jim. And they weren't just, you
know, passing acquaintances. They co -edited
the school paper, The Lion's Roar. And they even
co -wrote a satirical play together. This is
early days, but they're already honing that shared
sensibility. That's amazing. Two guys who become
central to this huge comedy hit starting out
editing high school paper together. It speaks
to, I don't know, talent, finding talent early.
Yeah, and Novak carried that intensity right
into Harvard, graduated in 2001, majored in English
and Spanish literature. But let's look closer
at his academic work there. The honors thesis.
This links back to film, doesn't it? It does.
He wrote his honors thesis on the films of Shakespeare's
Hamlet. Now think about that. He's not just studying
the play, he's studying adaptation. Ah, how the
story changes across mediums. Exactly. Structure,
reinvention. How do you take this core narrative,
Hamlet, and rebuild it visually? It's basically
analyzing the same problem he'd face adapting
The British Office. He was thinking like a technical
writer about film way before he wrote a pilot.
That's a huge range, though. Deep Shakespeare
film analysis on one hand and then writing, say,
Diversity Day for The Office on the other. But
it's connected, right? It's all structure and
narrative. And while he was doing the heavy academic
stuff, he was also performing. He joined the
Harvard Lampoon, you know, comedy writing powerhouse.
Right. And he performed in this variety show
called The BJ Show. So it was always this blend.
Deep analysis and practical performance. OK,
so 2001, he graduates, heads to L .A., starts
putting that structured comedy brain to work
in stand up. Did it take long to get noticed?
Seemed pretty quick. He was hungry. His first
official stand up gig was recorded like October
10th, 2001 at the Hollywood Youth Hostel of all
places. Wow. And by 2003, just two years later,
Variety picks him as one of their 10 comedians
to watch. That gets him spots on Comedy Central's
Premium Blend, Late Night with Conan O 'Brien.
But his first big TV splash wasn't stand -up
or sitcoms. It was. Well, it was pranking celebrities.
Yeah, punked. A bit of a curveball, maybe, but
crucial for visibility. 2003, season two, he's
Ashton Kutcher's main accomplice on the ground.
Right, setting up Hilary Duff, Usher, Mia. Exactly.
And, okay, maybe it seems like just fun and games,
but think about it. It forces him to improvise,
manage narratives happening in real time, perform
under pressure, good training in a weird way.
And even before Punk'd, he already had a foot
in the door with traditional TV writing. Yeah,
a small gig but important. He wrote two episodes
for a WB sitcom called Raising Dad. That was
back in 2001, 2002. So right from the start in
L .A., he's juggling stand -up, acting, writing,
always multitasking. That really sets the pattern
for his whole career, doesn't it? Absolutely.
And all those threads, the writing, the performing,
the analysis, they just perfectly came together
in the office. This was the gig that defined
him, obviously. But not just as Ryan, the actor.
It really made him a powerhouse behind the scenes.
And the way he got cast is brilliant. It wasn't
even a standard audition, was it? No. It's pure
recognition of talent. Greg Daniels, the executive
producer, saw Novak do stand -up, heard his opening
joke, apparently, and just thought, I want to
do something with him. It wasn't about finding
someone for a pre -written part. It was about
hiring that specific comedic brain. And then
he gets cast as Ryan Howard, the tump, who kind
of becomes this perfect symbol for, well, for
a certain kind of modern ambition. Detached,
maybe too smart for the room, but still wants
to climb. Totally. And that character got extra
layers, didn't it? Because of the real life stuff
happening off screen. Ah, the Mindy Kaling connection.
Kelly Kapoor. Right. The sources all talk about
their on -again, off -again relationship and
how it often seemed to, well, mirror the crazy,
toxic, but somehow really compelling dynamic
between Ryan and Kelly on the show. It blurred
the lines, you know, fed the comedy. Yeah, life
imitating art imitating life. But the bigger
story here, maybe, is his role as one of the
show's architects. He wasn't just reading lines.
He was in the original core group shaping the
whole thing. Oh, completely central. He was one
of the original writers from day one. Alongside
Greg Daniels, Mindy Kaling, Michael Schur, Paul
Lieberstein. That's the brain trust. And over
the show's run, he wrote 15 episodes. 15. That's
a huge contribution. Like being the head writer
for a season and a half, basically. It's massive.
And we need to look at which episodes he wrote.
They weren't just filler. They often set the
tone or took big risks. Like Diversity Day. Season
one. Exactly. WGA nominated, too. That episode
is crucial because it establishes the whole show's
M .O., right? Taking super uncomfortable social
topics, filtering them through Michael Scott's
profound cluelessness, but also his weirdly good
intentions. Yeah, it's a tightrope walk, tonally.
You need real control to make that level of awkwardness
funny without just being offensive. It feels
like applying that analytical brain to social
dynamics, but using jokes as the tool. Then think
about something later, like Scott's Tots from
season six. Oh, God, Scott's Tots. Probably the
most famously painful episode ever. Right. Pure
cringe comedy, but brilliantly structured. Michael
promising college tuition to kids years ago.
You just know it's going to end badly. Novak
directed that one, too. And he just leans into
the awkwardness, uses the mockumentary style,
the silences, the reactions. It's sustained comedic
tension. Yeah. Masterful, really. He also got
a WGA nom for local ad in season four. So writing,
directing, that kind of consistent quality work
naturally led to him becoming a producer, a real
leader on the show. Yeah, the industry certainly
noticed. He got two Screen Actors Guild Awards
with the ensemble, a Writers Guild Award for
his writing, and the show got five straight Emmy
noms for Outstanding Comedy Series while he was
a key producer -writer. That's 2007 to 2011.
He was officially named an executive producer
around season seven. He wasn't just a participant.
He was helping steer the ship. And directing,
too. You mentioned Scott's Tots. He directed
others as well, right? Wow. Bringing that film
analysis background into play. Definitely. Besides
Scott's Tots, he directed the seminar in season
seven. Season eight premieres The List trivia.
He even directed some of the webisodes like The
Office, Blackmail. He was clearly comfortable
wearing multiple hats on set, using it as a lab
almost. OK, but then comes this really interesting
moment, a major pivot point. The sources say
he was offered the absolute top job for the final
season. and turned it down. That's right. He
was offered the showrunner position for season
nine. That's that dream job in TV comedy. Total
creative control, big payday, the works. But
he said no. He confirmed later, I think in 2021,
that his, quote, fire for the job had burned
out. He felt he'd done what he could do within
that structure. He'd mastered it maybe and needed
a new challenge. That tells you a lot about him,
doesn't it? It's not about power grabbing. It's
about avoiding getting stale creatively. He prioritizes
the challenge, the reinvention over just climbing
the industry ladder. Exactly. Yeah. He did come
back for the finale, though. Made sure Ryan Howard
got a proper sendoff. But his focus had already
shifted. Right. So after deliberately stepping
back from the peak of The Office, Novak starts
making these really strategic moves into film,
picking supporting roles, often dramatic ones,
working with really interesting directors. Yeah,
looking at his filmography from, say, the late
2000s into the mid -2010s, it definitely feels
like a conscious effort. Like, OK, I'm not just
Ryan Howard. I'm a serious actor. Highly strategic.
Pretty quickly, 2009, he pops up in Quentin Tarantino's
Inglourious Bastards. Right, as PFC Smith Sinutovic.
A small part, but very serious in that movie.
Exactly. Working with Tarantino, that's like
a PhD in film structure right there. And it put
him in a totally non -comedic light. Before that,
he'd done Supporting Bits and Reign Over Me in
2007, and Judd Apatow's Knocked Up, also 2007.
And then in the mid -2010s, it seems like he's
drawn to films based on true stories or with
strong narrative structures. That's a good observation.
He plays Robert B. Sherman, one of the Sherman
brothers, in Saving Mr. Banks in 2013. That's
about the making of Mary Poppins, so he's embodying
a real person within this big story about storytelling.
Then he jumps into a totally different world.
Yeah, the superhero world. He plays Alistair
Smythe in The Amazing Spider -Man 2 in 2014.
Shows he's willing to play in those big franchise
sandboxes. But maybe the role that really showed
his dramatic chops was the founder. I think so.
That's the 2016 film with Michael Keaton as Ray
Kroc. Novak plays Harry J. Sunborn. The finance
guy behind McDonald's success. Exactly. The guy
who figured out the real estate model. It's a
crucial, serious role. Yeah. And Novak is really
convincing as this sharp, no -nonsense financial
architect. It proved his acting wasn't just limited
to comedy or mockumentary. Okay, before we leave
film, gotta mention the lighter side, too. He
did voice work. Oh, yeah. Gotta pay the bills,
right? And reach a different audience. He voiced
Baker Smurf in the Smurfs movie in 2011 and the
sequel in 2013. Baker Smurf. Okay. Hey, it's
smart. Voice work at a huge kids franchise. Yeah.
Keeps your name out there. Minimal effort visually.
Practical career move. Fair enough. Okay, shifting
back to TV after The Office. He didn't completely
cut ties, especially not with Mindy Kaling. No,
that partnership is incredibly strong. He showed
up on The Mindy Project, starred in five episodes
as a character named Jamie. But more than that,
he was a consulting producer for the first season,
kept his hand in, creatively supporting her vision.
And he wrote and directed for her show, too,
still wearing multiple hats. Yep, wrote and directed
episodes, including one called Harry and Sally.
That writer, director, producer, actor combo.
It's just his default mode, it seems. And then
to prove he was serious about drama, he dives
into maybe the most challenging dialogue style
on TV. Aaron Sorkin. The newsroom. Yeah. In 2014,
he gets this recurring role for four episodes
playing Lucas Prude. That's like going from swimming
laps to swimming the English Channel dialogue
-wise. Totally. Sorkin's stuff is relentless.
Fast, dense, super smart, taking that role. That's
deliberately choosing a difficult challenge,
pushing himself way outside the mockumentary
comfort zone. He really does seem committed to
just constantly adding different skills, different
experiences to his toolkit. Never stops diversifying.
And yeah, for the trivia buffs, he's done fun
cameos, too. He was Mr. Egypt on Community, popped
up in Crazy Ex -Girlfriend. And more recently,
just last year, 2023, he voiced the dog 630 in
Lessons in Chemistry. Oh, right. And he even
won a Celebrity Jeopardy. So, you know, he's
engaging across the whole spectrum. Eyebrow drama,
voice acting, game shows. He adapts. Okay, this
next phase feels like the most radical shift
yet. He moves away from performing almost completely
for a bit and goes full on into literature and
even tech. This is where that Harvard English
major really comes roaring back, isn't it? This
is pure intellectual Novak stepping forward.
April 2013, the office isn't even over yet, and
boom. Alfred Enoff announces this massive book
deal, seven figures, two books. Wow. And the
first book is pitched as, like, woody allen style
short fiction witty philosophical little story
that book was one more thing stories and other
stories came out in 2014 64 stories That's a
lot of concise narrative structures. How did
it actually do? It did really well. It was a
genuine success, commercially and critically.
Spent six weeks on the New York Times bestsellers
list for hardcover fiction. It basically proved
he could write outside of a TV writer's room.
That he understood short fiction, which is all
about nailing structure and impact immediately.
Very different from TV writing. Kind of like
the discipline of a stand -up joke, almost. Exactly.
Perfect analogy. But the really huge success,
the one that made him a household name in a totally
different sphere, was the children's book. Which
seems so. Left field, right? For the guy who
wrote Scott's Tots. Yeah, the book with no pictures,
that thing was everywhere. Everywhere is an understatement.
He signed a separate deal with Penguin for it.
The success was just phenomenal. As of early
2021, it had spent 174 weeks on the New York
Times picture book bestseller list. That's over
three years. And 34 of those weeks were at number
one. What was the magic? It's such a simple concept.
It's genius because it's pure structure as the
joke. The whole premise is it's a picture book,
but the rule is the adult has to read every single
word out loud no matter how silly. Bork. Blur.
Right. It forces the adult reader into absurdity.
Exactly. It weaponizes the text against the reader
for the child's amusement. It's all about the
power of the written word. Novak himself said
he wrote it because, and this is a quote, to
me, there's no more meaningful, important, or
exciting rule to introduce to children than the
power of the written word. He uses the structure
of the book itself to make that point. That quote
connects everything, doesn't it? Language, structure,
rules, control. It's like a meta commentary on
how we follow rules, even in a play. Precisely.
And he even released a follow -up in 2019, My
Book With No Pictures, which is like a fill -in
-the -blanks version, handing that power over
to the kid. He kept writing other stuff, too.
Essays for The New Yorker, Playboy, contributed
to Tim Ferriss' Tools of Titans. Always writing,
always analyzing structure. Okay. Master TV writing,
short fiction, smash hit children's lit. So the
obvious next move for a structuralist is a social
media app. Yeah, the tech venture. It's maybe
the most interesting failure because it reveals
so much. October 2015, Novak and a co -founder,
Dev Flaherty, launched the List app for iOS.
The concept was literally, quote, we just love
lists. They're the best. I remember this. It
felt like trying to bring order to Internet chaos,
making social media about curated, structured
lists. And that's the perfect analysis. It was
a structuralist solution to a messy behavioral
space. For Novak, a list ordered ideas is like
the ultimate short form narrative. He wanted
to force online chatter into that neat, tidy
format. Did it get any traction? Some initial
buzz. Got nominated for a Webby Award in 2016,
which is respectable. But ultimately. Ultimately
didn't stick. They rebranded it LydotST, put
it on Android in 2016. But people just didn't
interact that way online, I guess. It required
too much effort, too much deliberate curation
compared to, you know, just firing off a tweet.
It shut down in September 2017. Lack of users.
Which is fascinating, right? Because the failure
reinforces his core identity. He tried to impose
his beloved structure onto the wild messiness
of social media. And the messiness won. Structure
failed against chaos this time. Yeah, exactly.
So after that list app experiment, Novak seems
to regroup and consolidate. He enters what feels
like his current phase, the full -blown auteur.
He's creating, writing, directing, producing,
and starring in his own stuff now. taking complete
control. And the first big project showcasing
that total control was the FX anthology series,
right? The premise, yeah, back in 2021. He was
the creator, writer, director, exec producer,
everything for FX on Hulu. And an anthology,
that's maybe the ultimate test of versatility,
short of a movie. You build a whole new world,
new characters, new tone, every single week.
And he wrote all five episodes himself, tackling
some pretty edgy, topical stuff. Oh yeah, the
titles alone tell you that. Social justice sex
tape? Moment of silence, butt plug, he directed
a couple of those too. This wasn't safe network
comedy anymore. This was sharp, dark, social
satire. Drawing on everything he'd done before,
but pushing it somewhere new. Okay, so anthology
series done. The next logical step for the auteur
is the feature film directorial debut. Full control,
big screen. Vengeance, 2022. And again, he did
it all, wrote it, produced it, directed it, and
starred as the lead character, Ben Malowitz,
this writer guy who goes to Texas to investigate
the death of a woman he barely knew. And that
production had its own challenges, didn't it,
thanks to the pandemic? Oh, yeah. The sources
mentioned got shut down hard by COVID, started
filming March 2020, had to pause, didn't finish
until January 2021. Shows some serious grit,
seeing a big personal project through that kind
of disruption. And Vengeance itself feels like
a culmination, doesn't it? It blends genres.
It's a mystery, kind of a thriller, but it's
also funny. And it's got all this commentary
about the culture clash, urban versus rural America.
It really pulls together all his threads. The
sharp dialogue from his comedy writing days,
the deep social observation. his Harvard analysis,
the dramatic acting chops he honed in films like
The Founder. It's structurally complex, but accessible.
Smart commentary wrapped in a genre package.
So looking ahead, we should probably expect him
to keep prioritizing projects where he has that
full creative control. Seems likely. That's the
auteur path. Interestingly, even while Vengeance
was in the works, back in May 2020, it was announced
he's writing an exec producing a new show for
HBO Max called Young People. A multicam comedy.
Oh, back to multicam, the traditional sitcom
format. Yeah, which is fascinating. It's like
he wants to take that very structured, traditional
form, but apply his own unique vision to it.
Now that he's the one fully in charge, testing
his structural ideas in a different container.
And he's not giving up acting entirely. People
will still see him in other people's projects.
Nope. Seems he's keeping a hand in. He's listed
in the cast for The Devil Wears Prada 2. Apparently
it's filming now, aiming for 2026. So he can
maintain that acting profile in big studio movies
while also developing his own more personal writer
-director work. It's a smart balance. collaboration
and independence. All right. So to wrap up our
dive into BJ Novak, the creator, we should probably
touch on some of the key personal connections.
And obviously, the biggest one has to be Mindy
Kaling. That relationship spans decades now.
It's really one of the most unique and enduring
partnerships in Hollywood, isn't it? Started
romantic, got fictionalized on The Office, but
then evolved into this incredibly deep, supportive,
creative friendship. They were arguably the engine
behind so many of Ryan and Kelly's best, most
unhinged storylines. And he described her in
really powerful terms, didn't he, on NPR's Fresh
Air? He did. He called her, quote, the most important
person in my life. Which, coming from someone
generally quite private, says everything about
the depth of that bond. It's clearly way beyond
just colleagues or even just friends. It's foundational.
And now it's literally family, right? He's godfather
to her kids. Exactly. Godfather to her first
two children. That really cements it as this
permanent family -level connection. It's not
just about working together anymore. It's about
life. Okay. And what about his more recent personal
life? Any updates there? Well, the sources we
looked at indicate he's reportedly dating Delaney
Rowe. who's a big creator on TikTok. That started
getting attention late 2024 and seemed confirmed
around April 2025. Interesting. Shows he's still
connected to current culture, even as he's doing
these big literary and film projects. Yeah, bridging
different worlds, as always. Okay, finally, we
have to talk about the weirdest footnote in his
entire career, the stock photo thing. Oh my God,
it's hilarious. And so perfectly ironic for a
guy obsessed with controlling his narrative.
Somehow, somewhere, a photo of BJ Novak ended
up in the public domain as a generic stock photo.
And now it just pops up randomly on products
worldwide. Yep. Without his permission, without
his knowledge, it's the ultimate loss of control.
His face is just out there selling stuff. Do
we know what kind of stuff? The source has mentioned
it's been seen on all sorts of random international
products. The specific example given was, wait
for it, a Calvin Klein cologne in Sweden. No.
Ryan Howard's face selling Swedish cologne. Apparently
so. And Novak himself is reportedly just baffled
by it, has no idea how it happened. It's like
the universe playing a prank on the ultimate
planner. A little reminder that sometimes things
are just weird and chaotic. Hashtag head outro.
okay so we started this whole deep dive asking
you know is bj novak just ryan howard and i think
we can safely say unequivocally no not even close
what we've seen is this uh this really singular
creative figure who's just constantly successfully
pivoted comedy series film acting best -selling
literature for adults and kids tech Yeah, from
editing the high school paper with John Krasinski
to analyzing Shakespeare films at Harvard to
writing iconic sitcom episodes, becoming a number
one bestselling author, launching an app, directing
a feature film. It's an incredible trajectory.
And if you try to connect all those dots like
we set out to do. The connection really seems
to be that deep foundational understanding of
story structure. He gets how narrative works
on a fundamental level, whether it's a list or
a kid's book designed to be read aloud or a mockumentary
or a dark indie film. He sees the underlying
architecture. And he seems driven by mastering
those different structures. Once he feels he's
cracked one, he moves on to the next intellectual
challenge. Exactly. It's about the structure,
the execution, the precision of the language.
That's what matters to him, regardless of the
medium or the audience. So that leaves us with
a final thought for you, the listener, to chew
on. We've seen him tackle... Comedy, drama, kids
lit. He's always looking for structures to play
with, right? Right. So given that deep background
in analyzing classics, remember the Hamlet thesis.
And now he's involved in the Devil Wears Prada
2, which comes from a book. What's next? Yeah,
what classic genre or maybe what really ambitious
literary adaptation might he try and reinvent
now that he's got this full auteur toolkit? Could
he do, I don't know, a Western? A musical. A
musical. Adapt a dense historical novel. Who
knows? But given his track record, you can bet
it won't be predictable. With B .J. Novak, the
only real certainty seemed to be the next pivot.
Keep watching.