Welcome to the Deep Dive. This is where we really
tear into the sources you give us. We pull out
the key insights, the stuff that surprises you,
maybe makes you think a bit differently. Today
we're looking at Rick Glassman. He's a comedian,
actor, writer, director, a multi -hyphenate really,
and his career path is fascinating. It's kind
of a roadmap, isn't it? From stand -up ambition
to these really personal and acclaimed acting
roles. Absolutely. Glassman's journey is, well,
it's all about the pivots. You know, it kicks
off with that classic comedy dream, then moves
into the whole network sitcom world. But then
things take this really profound turn after a
personal diagnosis he received as an adult. So
our mission today in this deep dive is basically
to track that evolution. How did that self -discovery
shape his work? How did it lead to these incredibly
authentic roles in Hollywood? It's like he turned
this private knowledge into a real professional
advantage. Yeah. And we've got a good stack of
sources here. Lots of biographical stuff, career
milestones, press coverage, especially around
those big recent roles on Amazon and ABC. We're
not just making a timeline, though. It's more
about looking at how his mindset. which seems
kind of strategic, almost entrepreneurial from
early on, helped him grab onto every creative
chance he got. Right. So let's just lay out the
basics first, get everyone on the same page.
Rick Glassman, born July 23, 1984. That makes
him 41 now. American comedian, actor, writer,
director. You probably know him from Undateable,
playing Burowski. But maybe more recently, his
roles in, as we see it, as Jack Hoffman. Incredible
performance. And Edward in Not Dead Yet. Okay,
so we're going to unpack that whole journey right
from the start. in Ohio through the comedy scene,
the sitcoms, and then really dig into how that
personal diagnosis intersected with his art and
led to this focus on authenticity on really big
platforms. Okay. So to really get Glassman, you
got to look at where he started, those foundations.
He's got those solid Midwest roots, the source
to say born in Shaker Heights, which is, you
know. Pretty well -known Cleveland suburb. But
he actually grew up right next door in Orange,
another suburb. It might seem like a small detail,
but that specific regional background often fosters
a certain kind of resilience, maybe a practical
approach to things. Yeah, and that practicality,
that kind of business sense, seems like it might
run in the family. His background's diverse,
father's Jewish, mother's Italian descent. But
let's talk about his dad, Steve. There's an interesting
detail in the sources about his career. He started
out as a restaurateur, right? before switching
gears in the late 90s, became part owner of a
carpet store, Marshall Carpet One and Red Gallery
in Mayfield Heights. Exactly. And look, that
carpet store detail, it sounds like just, you
know, trivia. But stick a pin in that because,
as we'll see way later on, that specific family
business, it actually weaves directly back into
his creative work now out in L .A. It suggests
he had this early exposure to an owner's mentality,
maybe not just doing a job, but like owning the
whole thing. OK, interesting. Now, education.
This period seems full of, well, not contradictions,
but interesting paths not taken, right? Before
he fully committed to comedy, he graduated from
Orange High School in 2002. And here's one of
those amazing little details you find digging
through sources. He played high school basketball.
Which is cool, yeah. But the really wild part
is who his team played against. They competed
directly against St. Mary High School. And who
was leading that team at that exact time? LeBron
James. That's incredible. It's such a great image,
isn't it? You've got this guy who's going to
become known for this very self -aware kind of
awkward observational comedy. Yeah. And he's
on a basketball court facing off against like
the most hyped high school athlete maybe ever.
It really highlights that early mix of, I don't
know, competitiveness maybe. Right. And this
eventual path into art that really values vulnerability.
Totally. But the path wasn't straight to comedy,
not at first. He went to Kent State University,
graduated in 2006, got a degree in marketing,
which, you know, that's about as practical and
business oriented as you can get. It's the safety
net degree. But hold on. So he's got the marketing
degree sorted, maybe picking up business vibes
from his family. And yet the sources say he was
also taking theater classes while he was in college.
So what happened right after graduation? That
must have been a key decision point. It really
was. And the choice he made was, well, pretty
bold, risk -taking. Our sources confirm it. After
getting that marketing degree, he seriously considered
law school. Wow. Law school. Yeah. The ultimate
stable, respectable path. Right. But instead
of hitting the LSAT books, he dives headfirst
into stand -up. Did his first official gig at
the Cleveland Improv in 2007. That's a massive
pivot. Like the complete 180 from law school.
It really suggests that maybe the creative or
entrepreneurial drive was just stronger than
the desire for security. But that marketing degree
probably wasn't wasted, was it? That knowledge
about branding, audience. That must have come
in handy later when he started producing his
own stuff. He knew how to sell himself, presumably.
Oh, absolutely. That strategic thinking definitely
plays a role later. And that self -marketing
needed a bigger platform pretty quickly. So 2008.
He makes the move. The classic comedian pilgrimage
to the West Coast lands in Los Angeles. And,
you know, moving to L .A. is one thing, but actually
getting stage time and building a reputation
is tough. He managed it, though. Started performing
regularly at the Comedy Store. Right. And for
anyone listening who doesn't know the L .A. scene,
the Comedy Store isn't just some random club.
It's legendary. It's intense. It's where you
really have to prove yourself. Getting regular
spots there means you're in the mix. You're getting
seen by industry folks. You're honing your act
under pressure. You have to figure out your voice.
And that work, that honing, it definitely paid
off. 2013 was a big year for him. He got invited
to the New Faces Showcase at the Just for Laughs
Comedy Festival in Montreal. Now, for people
outside the industry bubble, this isn't just
another festival gig. This is the showcase. Yeah,
it's basically the industry saying, OK, pay attention
to these people. Every agent, manager, casting
director, producer, they're all watching New
Faces. Getting picked means you're officially
on the radar. You're tapped as someone likely
to. break into TV and film like imminently. Yeah.
It's a direct line from the club stage to the
casting office. So, yeah, that new faces spot
was the rocket fuel, really. If part one was
about, you know, finding his feet on the comedy
stage, part two is where he lands professionally
in Hollywood, gets that foothold in the very
competitive network sitcom world. And it happened
pretty quickly after Montreal with the NBC show
Undateable. OK, let's unpack this Undateable
breakthrough because the way it happened is kind
of cool. It shows the power of just being seen.
Right. It wasn't like a huge cattle call audition
process. The sources say Bill Lawrence, you know,
the creator of Scrubs, Ted Lasso. Huge name.
He actually saw Glassman and Brett Morin performing
live. Yeah, just saw their set at the Hollywood
Improv. And apparently, right then and there,
invited both of them to audition for Undateable.
Wow. And they both got it. Landed series, regular
roles. They joined a pretty solid cast, too.
Chris Delia was in it, Ron Funches, David Finn.
Glassman played Burski. He was one of the regulars
at the bar that Brett Morin's character owned.
He was on for all 36 episodes from 2014 to 2016.
And something really interesting about Undateable.
which maybe gets forgotten, is that final season.
Season three, they did the whole thing live,
right? Yeah, they did. Which is crucial, I think,
for understanding Glassman's skill set. Doing
a multi -cam sitcom live, week after week, that's
intense. It's like theater discipline meets stand
-up timing and improv skills. You need serious
confidence chemistry with the cast. Skills he'd
definitely been sharpening at the comedy store.
It was basically performance boot camp. But here's
where it gets really interesting, where you see
that, maybe that marketing degree and that creator
impulse kick in again. He didn't just settle
into being Borowski, the sixth lead on the call.
While Undateable was still on the air, he actually
pitched an idea back to Bill Lawrence. And that
idea became its own thing. An NBC -produced web
series spinoff called The Sixth Lead. Yes. This
is such a key moment. He goes from being an actor
in the show to being the creator of a related
show. He didn't just wait for the next acting
gig. He literally created one for himself and
one where he had total control. He wrote it,
he directed it, and he starred in it. All eight
episodes. And the concept was pretty meta, wasn't
it? The sources describe it as being about his
fictionalized day -to -day life as the sixth
lead, dealing with the relative obscurity of
being the lowest -billed guy on a hit show and
the style they compare it to. Curb your enthusiasm.
That tells you a lot, right? Self -deprecating,
awkward, observational. Totally. It's brilliant,
really, as a career move. It shows he understands
how to take a potentially frustrating situation
like maybe nobody recognizes you from the promo
photos and spin it into gold. Into content. Pure
meta comedy. But OK, doing a show about being
the least important guy on the main show. Did
that cause any weirdness, any friction with the
rest of the undateable cast? It seems like it
was the opposite, actually. Like it was an inside
joke. They were all in on Bill Lawrence himself
appeared in it. Other undateable cast members
popped up. Zach Braff was in it as himself. They
all played versions of themselves kind of reacting
to Glassman's characters, you know, ego or anxieties
about his status. It almost validated him within
that NBC world as someone who could create his
own buzz. And it wasn't just an inside joke.
He took that web series, edited it down into
a short film, and it won Best Short Film at the
IFS Festival in 2016. That's the Independent
Filmmakers Showcase in LA. That award feels significant.
It's external validation. He wasn't just the
funny guy from the sitcom. Now he's an award
-winning writer and director. Exactly. That win
coming right off the back of the sitcom really
cemented him as a proper multi -hyphenate, someone
who could generate his own material, direct it,
star in it, and get recognized for it. Okay,
before we move into the next big phase, we should
quickly mention he was also starting to stretch
into different kinds of acting roles around this
time, too. Show me more range. I did guest spots,
right? Adam Devine's house party, the comedians.
Yeah, but the really notable step, I think, was
playing Harold Ramis. That was in the 2018 Netflix
movie, A Futile and Stupid Gesture, about the
founding of National Lamboon. Playing Ramis,
I mean, that's comedy royalty, a legend known
for being this quiet intellectual force. Taking
on that role was a big leap. It moved Glassman
beyond the kind of self -aware comedy of Berthuiski
or The Sixth Lead. It showed he could handle
dramatic weight, portray a real complex person.
It proved he had those dramatic chops. Okay,
so we've traced the path. Right. Stand up sitcom
success, even directing wins. He hit those conventional
markers of success in Hollywood. But the thing
that seems to have really catalyzed the next
stage of his artistic evolution wasn't another
role or another show. It was something deeply
personal, a moment of self -discovery. Yeah,
this is where the story takes that profound turn
we mentioned earlier. The professional arc kind
of gets reshaped by the personal one. In the
late 2010s, so well into his adulthood, Glassman
was diagnosed with Asperger's syndrome. Our sources
consistently categorize him now as an artistic
actor and American autistic person. Getting a
diagnosis like that as an adult, after you've
spent... Decades just navigating the world without
that specific framework. Yeah. It must be incredibly
clarifying. He actually spoke about it really
powerfully. Told Forbes the diagnosis brought
this immense clarity. He said all of these seemingly
unrelated obstacles became patterns that made
sense. And importantly, he added, it's something
that I was and I'm proud of. Right. And what's
so compelling here is how quickly he seemed to
integrate that new self -understanding into his
professional life, into his art. You know, for
a lot of adults who get an autism diagnosis later
in life, it helps explain maybe why certain social
things felt harder or why some work environments
were challenging. For Glassman, it seems like
it also unlocked this deep artistic insight.
It gave him the language, maybe the internal
permission to tap into something really specific
and authentic for his characters. We should probably
just quickly touch on the terminology for listeners.
The diagnosis mentioned was Asperger syndrome,
which under current diagnostic standards falls
under the umbrella of autism spectrum disorder
or ASD. So in discussions about his work now,
you often see him referred to as an autistic
actor. And this clarity he gained, this self
-knowledge, it became a strength, something he
could actually use in his work. And he applied
it almost immediately and with huge impact. In
2022, he starred in that Amazon Prime video series.
as we see it oh yeah great show really great
show based on an israeli series called on the
spectrum it follows three roommates who are all
autistic navigating work friendship love and
the casting for as we see it was a big deal wasn't
it because they made a point of casting autistic
actors to play the autistic main characters which
brought this incredible layer of authenticity
glassman played jack hoffman one of the roommates
a series regular for all eight episodes Exactly.
And his performance as Jack, who's written as
highly intelligent, very logical, but also quite
rigid socially. It was widely praised. Critics
singled it out for feeling so real, so grounded.
This was a huge departure from, say, the broader
comedy of Bratuski on Undateable. Now, he was
working with such specificity, such nuance. He
was clearly drawing on his own perspective, his
lived experience to build that character. And
it wasn't just a one time thing. This focus on
authentic roles quickly became central to his
public identity as an actor. It led directly
to his next big network role, didn't it? On the
ABC sitcom Not Dead Yet, which started in 2020.
That's right. In Not Dead Yet, which starred
Gina Rodriguez, Glassman played Edward. And Edward,
his character, was also explicitly written as
autistic. He was the roommate of Gina Rodriguez's
character, a series regular again. The show ran
for two seasons, just wrapped up in 2024. So
when you connect those dots, as we see it, and
then Not Dead Yet. The pattern is really clear.
He goes from playing more general characters
to taking on these two major high profile roles
where the character's identity is explicitly
autistic, mirroring his own recent diagnosis.
But I wonder, is there a risk there? The risk
of being typecast, maybe playing two prominent
autistic characters back to back? How does an
actor balance that kind of authenticity with
wanting artistic range? That's a really valid
question. It's something actors who find success
playing very specific types always have to navigate.
But the sense you get from the sources and from
how he talks about it is that for him right now,
the importance of owning that narrative, of pushing
for authentic representation, that seems to outweigh
the fear of being pigeonholed. You could argue
that by being an openly autistic actor playing
these roles, he's actually redefining what rainy
means for him. His range isn't just about accents
or genres. It's about the incredible depth and
honesty he brings to representing a community.
his unique perspective as his primary acting
tool. That's a powerful way to frame it. He basically
took something personal, something maybe seen
as a challenge, and turned it into the absolute
core strength of his most visible work. That's
taking self -knowledge and making a professional
asset. Right. And while those big acting roles
on Amazon and ABC give him that mainstream visibility,
we also see Glassman, the creator, the entrepreneur,
still very much at work controlling his own platform,
which brings us to his podcasting work. This
is where those directing and production skills,
the ones we saw emerge with the sixth lead, really
continue to shine. Yeah, let's talk about Take
Your Shoes Off, or TYSO. That's his podcast,
started in 2019. On the surface, it's interviews,
right? Mostly long -form chats with comedians,
people in the industry. It is, but it's how he
does it that's so unique. He completely refuses
to just do the standard podcast format. You know,
two people, two mics, maybe a static camera shot.
This is where his comedy timing meets those directing
and editing chops he honed. The sources point
this out. Often, right in the middle of a conversation,
he'll suddenly cut away. He'll superimpose these
bizarre digital animations or cut to these highly
stylized, almost surreal dramatized scenes featuring
him and his guest. Right. It's not just like
adding a funny sound effect. It's way more elaborate.
Like if a guest says something that confuses
him and something kind of weird, he might suddenly
cut to this short animated sketch where they're
like in a spaceship arguing about it. Or maybe
it's suddenly film noir lighting and he's interrogating
them. It's a total commitment to the bit, whatever
that is. bit is. It makes the show stand out
visually and tonally in the, let's face it, very
crowded podcast space. Totally. It elevates the
whole thing. It's not just a recorded conversation.
It's a produced piece. It reinforces that identity.
We talked about the creator who demands full
control over the style and the edit. And it goes
back to that strategic mindset, too, right? He's
making content that's memorable, shareable, distinctly
his. And speaking of branding and strategy and
things coming full circle, this is where we get
that amazing connection between part one, his
early life. and this current creative work. His
podcast, TYSO, features advertisements that he
directs himself. From Marshall Carpet One and
Rug Gallery. Yes, this is the detail we flagged
earlier. That is the exact same carpet store
co -owned by his dad, Steve, back in Ohio. It's
incredible. It's such a fascinating, deliberate
link. Think about it. This guy starred on NBC,
starred on an Amazon drama, won awards for directing
his own spinoff, and he's also serving as the
creative director, basically, for his family's
local carpet business back in Mayfield Heights,
making their commercials. It perfectly merges
the marketing degree with the directing talent.
He's using his L .A. platform, his skills, his
name recognition to make high quality ads for
the very business that maybe gave him his first
glimpse of entrepreneurship. It closes this professional
loop in a way you rarely see from people who
found success in Hollywood. He really does seem
to have that. owner's mindset about everything
he does. Absolutely. It shows he operates with
this fierce independence. Doesn't matter if the
platform is huge like network TV or loose like
a podcast or even a local business ad. He's controlling
the creative. He's generating different revenue
streams and he's keeping that connection to his
roots alive. So just to round things out. Yeah.
What else has he been up to lately on screen?
He's still taking on interesting supporting roles,
right? Like in that Netflix movie, Old Dads from
2023. Yeah. Played Hunter Lewis. Yep. And he
also had a role as Nico in an episode of that
2024 show, Nobody Wants This. But, you know,
adding to the list of unexpected income streams,
we can't forget the McDonald's commercials. Right.
Our sources mentioned six McDonald's commercials
he was involved with. Six of them. Mostly. Voiceover
work? Five voiceovers, yeah, and one where he
actually appeared on camera. That's just the
reality of the working actor, the working multi
-hyphenate, isn't it? That kind of consistent
commercial work, it provides the financial stability
that lets you take risks on the more personal
passion projects like 2YSO or those deeply authentic
roles like Jack Hoffman. It all fits together.
Hashtag, hashtag, hashtag, outro. Okay, so let's
try and synthesize all this. Great. What's the
big picture takeaway from Rick Glassman's career
so far? We started with this young guy in Ohio,
you know, maybe thinking about law school, then
boom, sharp pivot into standup comedy, grinding
it out in Cleveland, then LA, finds that big
break on a network sitcom, undateable as the
quote unquote sixth lead. But then crucially,
he doesn't just ride that wave. He immediately
uses that platform to write, direct, and star
in his own award -winning meta series, The Sixth
Lead. He takes control. Right. But the biggest
transformation. The real hinge point wasn't professional.
It was personal. It was that adult diagnosis
of Asperger's syndrome, understanding himself
as autistic. And instead of seeing that as, I
don't know, a barrier or something private, he
integrated it directly into his work. That self
-knowledge became the bedrock for his most powerful,
most acclaimed roles to date on major platforms
like Amazon and ABC. It wasn't a limitation.
It was his unique strength. Exactly. So the thread
running through it all, I think, is this power
of knowledge and control, whether it was the
market knowledge from his degree or the stage
knowledge from stand -up or ultimately the self
-knowledge from his diagnosis. He consistently
takes insight, personal or professional, and
applies it directly to create something tangible,
something uniquely his. His path really underscores
the value of embracing your whole self, complexities
and all, as your most valuable asset in whatever
you do. Yeah, that journey from playing basketball
against LeBron in high school to eventually directing
commercials for his dad's carpet store, all while
starring in these really significant representation
-pushing dramas based on his own experience.
It's a remarkable story of creative ownership.
Which leads us to maybe a final thought for you,
the listener. To chew on. We've seen how Rick
Glassman's diagnosis, something unexpected discovered
in adulthood, brought this immense clarity and
directly fueled his most distinctive work recently.
So the question is, how might you or how might
others leverage your own deeply personal experiences?
Maybe obstacles you've overcome, unexpected insights
you've gained about yourself, passions you thought
were unrelated to your real job. How could that
kind of unique self -knowledge be channeled to
create completely new, maybe more authentic and
powerful? opportunities in whatever field you're
in. Something to think about.