Welcome back to the Deep Dive. You know, we look
at a lot of source material here, try to figure
things out, give you that shortcut. Today, we're
tackling someone whose career path is, well,
honestly kind of baffling. Robert Allen Riggle
Jr. We're talking about a guy who spent 23 years
in the United States Marine Corps, rose all the
way up to lieutenant colonel, and at the same
time, somehow, became this huge face in comedy.
Sketch comedy, movies, TV. You name it. It really
is like two different lives, isn't it? And that's
our mission today, really, to look at these sources
and figure out not just that he did both, but
how. How did these things, you know, coexist?
Military service, combat experience, and then
boom, Saturday Night Live, The Daily Show. It
seems impossible. Right. The basic facts alone
just clash. Yeah. Born April 21st, 1970, Louisville,
Kentucky. Okay. But look at the education. University
of Kansas, he gets a B .A. in theater and film
in 92. Makes sense for an actor. But then just
five years later, 1997, he gets a Master of Public
Administration, an M .P .A. from Webster University.
Well, that M .P .A. is kind of the secret key,
isn't it? That five -year gap where he gets both
degrees. It's basically the blueprint for his
whole career. The theater and film B .A., that's
the creative path. Performance, improv, storytelling,
obvious. But the Master of Public Administration.
That's about leadership, management, policy,
logistics, running things, you know, like government
stuff or high level military. He was literally
training for two completely different, very demanding
professions. At the same time. Exactly. And the
career snapshot reflects that perfectly. Military
service. Yeah. 1990 right through to January
1st, 2013. Lieutenant Colonel. That's serious.
But smack dab in the middle of that, he's blowing
up in comedy. Yeah. Randy in Step Brothers in
2008. Officer Franklin in The Hangover in 2009.
Iconic roles. How do you even schedule that?
That's the million dollar question, isn't it?
The logistics are mind boggling. The Marine Corps
Reserve demands serious commitment, readiness
for deployment. And then you've got auditions,
shooting schedules, live shows and comedy. The
dedication required for either one is huge for
both. It's almost unbelievable. Let's rewind
a bit, though, to his early life, because this
split seems to start way back. Moved from Kentucky
to Overland Park, Kansas, when he was just two.
Shawnee Mission South High School. And even back
then, he was into performance school, radio,
TV stations. And here's a little tidbit. Voted
most humorous in his class. Graduated 88. So
the comedy bug was there early. Yeah, the talent
was obvious. But the path he took right after
high school, that's what's really interesting.
He joins the Marines in 1990. This is while he's
at KU, mind you. And he'd already gotten his
pilot's license. So the initial plan, according
to what we've read, was pretty straightforward.
Become a naval aviator, full -time pilot, active
duty. But then comes the pivot. And this is crucial,
right? This decision point is what makes the
whole dual career thing possible. He decides
not to go through with flight school. He realizes
that active duty flying would completely block
any chance of a comedy career. So he trades the
cockpit for the stage, essentially, and shifts
over to the Marine Corps Reserve. And that decision
changes the entire game. The reserves, well,
it's still a massive commitment. Don't get me
wrong. One weekend a month, two weeks a year,
typically. But it's not the constant full -time
demand of active duty. It allowed him the time
to pursue comedy. He could keep his military
commitment, rise through the ranks, deploy when
called up, which he did multiple times, and still
be available for auditions and gigs in New York
and L .A. He basically walked this logistical
tightrope for more than 20 years. It's kind of
incredible. 23 years. Yeah. And reaching lieutenant
colonel. That's not just showing up. That's a
serious, successful military career in its own
right. Absolutely. We need to be clear about
that. This wasn't some, you know, honorary role.
This was real service. He was a public affairs
officer based out of New York City for a lot
of it with a reserve unit there. And that job
involves, you know, being the military's voice
to the public, to the press. It's a leadership
role. High pressure, high visibility. And think
about the timing. Early 2000s, New York City.
Then 9 -11 happens. And the sources say he was
right there. involved immediately in the recovery
efforts at Ground Zero. Yeah, that's really grounding
detail, isn't it? While maybe other comedians
are worrying about their next open mic spot.
Riggle is boots on the ground in Lower Manhattan
after a national disaster, in uniform, leading
Marines. And his service wasn't just stateside
either. He deployed twice to Afghanistan, 2001,
2002, right at the beginning of the conflict,
plus assignments in Liberia, Albania, and Kosovo.
Okay, wait, let's pause on Kosovo, because that's
not just an assignment. That's where things get
really serious, militarily speaking. The sources
are clear. His time in Kosovo earned him the
Combat Action Ribbon, the CIR. Right. And for
anyone listening who doesn't know, the CIR isn't
handed out like candy. You don't get it for showing
up. It means you were there in ground combat
under enemy fire. Yeah. Actively participating.
So this completely shatters any image of him
being just a weekend warrior or, you know, a
PR guy behind a desk. He's a combat veteran.
While his comedy partner, Rob Hubel, might have
been doing improv back in New York, Riggle was
in an active conflict zone, possibly engaging
the enemy. The contrast is just stark. How do
you even process that? Yeah. Going from that
kind of life and death situation one week to
worrying about landing a punchline the next.
It suggests incredible compartmentalization,
mental discipline. Maybe something the Marines
instill. And look at his awards list. It really
backs up the depth of his service. It's not just
campaign medals for being in a place. It's recognition
for sustained high -level performance, both in
and out of combat. Let's break down a couple
of those awards just to give a sense of what
they mean. Okay, yeah. The Meritorious Service
Medal. He got two of those. That's for Outstanding
Non -Combat Service or Achievement. Getting it
twice suggests long periods where he was really
excelling in leadership, management, taking on
more responsibility, not just serving, but serving
well. And then there's the Navy and Marine Corps
Commentation Medal, the Joint Service Achievement
Medal. More recognition for specific acts or
periods of excellent service. Plus, you see his
deployment history right there in the medals.
Kosovo Campaign, Afghanistan Campaign, Global
War on Terrorism Service Medal. Right. And don't
forget the Humanitarian Service Medal, likely
tied to things like the 9 -11 recovery efforts
and the Armed Forces Reserve Medal showing his
long tenure in the reserves. Put it all together
and you see a picture of a really dedicated officer,
someone who stepped up for major conflicts, major
domestic crises for over two decades, all while
somehow. Building this completely separate career
in the madness of show business. Yeah. Understanding
that military foundation is so important because
you can really see how it informs his comedy
persona later on, especially when he hits the
big time. Exactly. OK, so let's pivot. Let's
talk comedy, because this whole time alongside
the Marines, the comedy career is bubbling up
and it really starts like for so many others
of his generation with improv, specifically at
the Upright Citizens Brigade Theater, UCBT in
New York. And the key relationship there is with
Rob Hue. They became this powerhouse duo at UCB.
They were part of that legendary improv troupe,
Respecto Montalban. That was really his training
ground, honing that comedic voice. Yeah, and
their main thing was a two -man show called Kung
Fu Grip. It was a big hit at UCB, ran for a long
time, got so much buzz, actually, that they got
invited to perform it at the HBO Comedy Arts
Festival in Aspen back in 2004. That's a major
stepping stone, getting noticed on a national
level. And that notice led to those early TV
spots, right? The talking head shows that were
everywhere then. Comedy Central's Best Week Ever,
VH1's A to Z. He was also on Bravo's 100 Scariest
Movie Moments in 2004. It was a smart way to
get screen time. He had this sort of authoritative
look, but he's using it for quick, funny commentary.
And all that momentum leads directly to the big
audition, Summer 2004, Saturday Night Live. And
it's kind of poignant, isn't it? He auditions
with Rob Hubel, his longtime partner. But only
Riggle gets the call. He joins as a featured
player for season 30, that's the 2004 -2005 season.
Only one season, but he definitely made his mark,
mostly with impressions. Yeah, he had a pretty
good stable. Larry the Cable Guy, Howard Dean,
Rick Sanchez, Mark McGuire, Toby Keith, he could
transform. But the thing people often remember
from that season, the really standout original
bit, was that one -off character. Leviticus.
Leviticus. The super loud, really aggressive,
almost violent street preacher. He just appeared
once on Weekend Update during the Christmas show
Robert De Niro hosted. It was pure, chaotic energy.
You could almost see, I don't know, maybe a hint
of that military intensity channeled into comedy.
It was jarring but funny. And here's a bit of
trivia for the deep dive. He was actually on
SNL before he was cast. Season 29, non -speaking
role in a pre -taped sketch. A parody of Fear
Factor, he played a dad whose divorce depended
on his kid eating maggots. Bizarre. Shows he
was already on their radar. So SNL ends after
one season. He heads back out, briefly has a
deal with NBC, with Hubel and others that doesn't
quite pan out. Happens all the time. But the
next big move, that was the perfect fit, the
role that let him truly merge the two sides of
his life. The Daily Show with Jon Stewart. Exactly.
September 2006. He comes in to replace Rob Corddry,
who was huge, big shoes to fill. But the format
was tailor -made for Wiggle. Because now... He
could explicitly use the military background.
He wasn't just another correspondent. He was
the show's military analyst. And they leaned
into that hard right from the start. He'd always
reference his service, joked about how his training
meant he could, you know, kill any other cast
member. It created this funny running gag, this
undercurrent of him being genuinely intimidating,
even in the writer's room. Yeah. And remember
that Marines in Berkeley segment? That was classic
Riggle Daily show. He goes undercover, dressed
as a hippie to sort of spoof the peace protesters
outside. a Marine recruiting station. But because
it's him with his actual Marine background, it
had this extra layer of authority. He could make
fun of it from the inside almost. It was brilliant.
He also did major field pieces for them, like
traveling to China for the 2008 Beijing Olympics.
Tape that whole series. Rob Riggle, Chasing the
Dragon. That's a big production. He's planning,
needs someone who can operate in, let's say,
complex environments. Maybe those PA skills came
in handy. Could be. He left the show in December
2008. The joke was he was leaving to go fight
crime. Classic wriggle deadpan. But his presence
lingered. Remember that cameo in 2010? when Will
Ferrell was on. Stewart and Ferrell were kind
of playfully trash -talking Riggle, and then
Riggle just walks onto the set. And the way Stewart
and Ferrell immediately snapped to attention,
got all polite and scared, it just cemented that
whole running joke about him being genuinely
feelsome. Oh, yeah. That was comedy gold. Using
your real -life persona as the punchline. Masterful.
Okay, before we get to the film stuff, there's
an important shift in his live performance around
this Daily Show time. Right. Good point. Up till
then, pretty much all his live comedy was...
improv or sketch. Needed a team, partners. But
starting around 2006, he begins developing a
stand -up act, solo act. And apparently John
Oliver, who he shared an office with at The Daily
Show, really encouraged him to do it. Yeah, Oliver
apparently told him, look, stand -up gives you
independence. You own it. You don't need a troupe.
So Riggle starts hitting the road, colleges,
comedy clubs, often touring with Oliver, other
Daily Show folks. It was a smart move. Gave him
another way to perform, another income stream,
right as he was... transitioning out of the correspondent
role and that independence that stand -up polish
probably helped him make the leap into becoming
this incredibly prolific supporting actor in
movies over the next 10 years or so oh absolutely
after the daily show he just carved out this
niche playing the intense guy the loud guy the
overly confident maybe slightly unhinged authority
figure yeah his film roles really lean into that
architect stepbrothers 2008 randy Will Ferrell's
awful co -worker, so aggressive, so inappropriate,
it's hilarious because he commits so hard. And
then the hangover in 09. Officer Franklin. Yeah.
The taser scene, classic. He's got that mix of
official power and just being kind of a jerk.
Sets the whole tone. Follow that with Detective
Evan Martin in The Other Guys, 2010. paired with
Damon Wayans Jr. always trying to one -up the
main characters. You see the pattern, right?
Aggressive, high -status dude, played for comedy.
You almost wonder if casting directors saw Lieutenant
Colonel on his resume and thought, okay, this
guy can pull off believable intensity. And the
list goes on. The internship, let's be cops.
Even my big, fat Greek wedding, too. He pops
up everywhere. And he branched out into voice
acting, too. Did the main villain, Aloysius O
'Hare? in the Lorax in 2012, showed he could
bring that energy even without being on screen.
That kind of versatility kept him constantly
working, not just movies, but big TV roles, too.
Yeah, on TV, he became super recognizable. Even
if people didn't know his name, they knew the
face. Gilthorpe on Modern Family, Phil Dunphy's
nemesis, that character was pure wriggle archetype.
Hyper -masculine bragging real estate shark.
Seven episodes of that. Hilarious. Again, you
see nods to his military past. He played the
president of the Navy literally on that adult
swim show, NTSS at the Juicy V. Pure parody leaning
right into his rank. He was also Mitch the Marine
Brother on Gary Unmarried and had a recurring
role on Wilfred. And it's cool that even while
doing all this mainstream stuff, he still collaborated
with his old UCB buddies, Hubel, Paul Scheer.
They did sketches for HBO's Funny or Die presence,
like Designated Driver, Death Hunt, kept those
improv roots alive. He had a couple of pilots
that didn't quite launch, too. A CBS sitcom called
Home Game with Mark Wahlberg producing. An NBC
pilot, The Pro, with Rob Lowe. Happens. But even
those misses didn't really slow him down because
by then he was moving into really high -profile
gigs. Hosting. Brand stuff. Yeah, these next
moves really cemented him as more than just a
supporting actor. He became a familiar face in
huge broadcasts. September 2012, he takes over
the comedy segment on Fox NFL Sunday from Frank
Caliendo. That's a massive audience every week
during football season. Different kind of comedy,
too. More about predictions, quick jokes, interacting
with the analysts, live TV pressure. And then
the ultimate commercial authority role. Colonel
Sanders for KOC, starting in 2016. He follows
guys like Norm Macdonald, Daryl Hammond. He's
literally wearing the white suit. Perfect casting
in a weird way. Plus, he hosted the ESPY Awards
back in 2012. Big stage, live audience, full
of stars. And the most recent thing a lot of
people probably know him from is Holy Molly,
the mini -wolf show from 2019 to 2022. He's the
color commentator alongside Joe Tessitore. Just
pure enthusiasm, absurdity, reacting to people
getting knocked into water by giant windmills.
It's kind of the perfect end point for this discussion,
isn't it? From earning a combat action ribbon
under fire in Kosovo to providing hilarious commentary.
on extreme miniature golf, the sheer range of
his professional life is just staggering. It
really is, and it points to this core ability,
maybe, to handle wildly different kinds of pressure
and performance, military discipline, comedy
chaos. He navigates both. But we do need to address
something else, his personal life, which took
a very public, very dramatic turn recently, and
it adds another much more serious layer to his
story. Yeah, it's part of the public record,
so we need to include it for the full picture.
He married Tiffany Riggle back in 1999. They
have two kids together. But they filed for divorce
in October 2020. And the details that came out
in 2021, well, they're pretty shocking. Very
different from the funny guy persona. Yeah, the
claim surfaced around June 2021. According to
the reports, Riggle alleged that his estranged
wife had hacked into his personal Apple account
and also that she had stolen money from his home.
These are serious accusations, obviously, pointing
to a really difficult separation. And it got
even more intense. Later that same month, Riggle
sought and was granted a temporary restraining
order. The reason? He apparently discovered a
hidden camera in his house disguised as a smoke
detector. Right. That detail is just wow. It
takes the conflict to a whole different level.
We're talking about alleged surveillance inside
his own home. And the scale of it. The reports
mention the camera allegedly had something like
10 ,000 videos stored on it. And Riggle claims
some of that footage backed up his earlier allegations
about the hacking and the theft. I mean, going
through a divorce is tough enough. Yeah. But
dealing with alleged hacking, theft, and finding
a hidden spy camera, that's like something out
of a movie, not the life of a comedian known
for playing goofy authority figures. It creates
this incredible, almost unbelievable contrast,
doesn't it? Here's a guy, a lieutenant colonel.
trained in intelligence, threat assessment, operating
in war zones. And he finds himself in this deeply
personal, highly public drama involving alleged
covert surveillance in his own private space.
The sources mentioned there was a follow -up
hearing scheduled too. specifically so a forensic
expert could analyze all that video footage from
the camera, which just underlines how serious
and complex the whole situation became. Yeah,
it's a very somber, a very complicated note to
touch on, but it does, in a strange way, tie
everything together. It shows this person who
has managed immense pressure, compartmentalized
drastically different lives, and navigated incredibly
high -stakes situations, whether on a battlefield,
a comedy stage, or, unfortunately, in a courtroom.
So wrapping this all up, after going through
all these sources, what's the main takeaway?
For me, it's just the sheer sustained dedication
to two profoundly different, incredibly demanding
paths. Lieutenant Colonel, combat vet, decorated
officer, and successful comedian, actor, host.
It's extraordinary. Absolutely. And, you know,
thinking back to that education split we talked
about at the beginning, the BA in film, but also
the Master of Public Administration, it really
makes you wonder, doesn't it? Wonder what? Well,
how much did that MPA training, which is all
about managing resources, strategic planning,
logistics, dealing with crises, how much did
that actually enable his success in comedy? We
think of the military side and the comedy side
as separate, maybe even conflicting. But maybe
the skills he learned as a Marine officer, the
discipline, the planning, the ability to perform
under intense pressure, to command a room, to,
you know, compartmentalize. Maybe those were
the very skills that allowed him to thrive in
the chaos of live comedy in Hollywood. Maybe
that military background wasn't just something
he juggled alongside comedy. Maybe it was fundamental
to his ability to do comedy at the level he did.
Something to think about, you know, how that
training translates across such a different world.