Welcome back to the Deep Dive. Today we're taking
a long, critical look at someone you probably
know best from behind the Weekend Update desk
at Saturday Night Live. Right. But there's way
more to him than just that. We're diving deep
into Colin Kelly. Just American comedian, yes,
but also a really accomplished writer, actor,
screenwriter. Born June 29th, 1982. Yeah. And
here's the thing. If you just see him as, you
know, the straight man next to Michael Che, you're
missing the the whole engine behind it, the intellectual
side that's driven one of the, frankly, most
durable careers in satire today. Absolutely.
That's exactly right. I mean, focusing just on
those few minutes swapping jokes each week, you
completely miss the well. The academic power,
the administrative skill that really built his
whole career path. Okay. Our sources today, they
give a really full picture. And honestly, kind
of a surprising one. We're going to track him
from a pretty serious academic start. Not where
you usually expect comedy writers to come from.
No, not at all. Right. Through getting hired
as a staff writer back in 2005, his times as
head writer multiple times, actually. And then
finally, him becoming the longest serving weekend
update anchor ever. He broke the record. So our
mission here. in this deep dive is really to
map out that foundation. How does a guy who studied,
you know, dense Russian literature at Harvard
end up being this sort of dominant dry voice
in late night political humor? We'll look at
how we use that sharp writing skill to get into
movies, write a... bestselling memoir, land these
big hosting gigs. Including that new pop culture
Jeopardy thing. Exactly. That was just announced.
Hosting for Amazon Prime Video. So yeah, we're
looking past the punchlines, really trying to
dissect how we built this success. Okay, so let's
unpack that. Starting right at the beginning
with those foundations, his roots, his academic
background. He was born in New York City, June
29, 1982, raised Catholic, grew up in Grimes
Hill, Staten Island. Staten Island. That geography
feels important, doesn't it? Yeah. It kind of
explains that grounded, maybe slightly outsider
view you get from a lot of Staten Island comics.
It really does. And the family background is
pretty telling, too. Right. It points to this
environment of like high pressure public service
kind of jobs. Right. His mother, Carrie J. Kelly.
She was the chief medical officer for the New
York City Fire Department. Wow. Yeah. I mean,
think about that role. The composure needed,
the huge decisions, especially after 9 -11. Intense.
And his dad, Daniel A. Chost, taught at Staten
Island Technical High School. So you see this
mix, his mom's precision, his dad's focus on
communication. It almost feels like it feeds
into his, you know. meticulous comedy style later
on. It really does build this kind of stable
professional structure, doesn't it? And that
professional bent, it seems like it runs in the
family. His younger brother, Casey Jost, he's
deep in the comedy world too. Writer and producer
for Impractical Jokers. Okay. And there's a cool
overlap. Casey was also in that movie Staten
Island Summer, the one Colin wrote back in 2015.
Huh. So the creative thing is definitely a family
affair. And you see that discipline right away
in his education. It's seriously elite. He went
to Regis High School in Manhattan, known for
being tough, academically graduated in 2000.
And get this, he was already editing the school
paper there at the Owl. So even then, he's practicing
editorial judgment, leading a team. But here's
where it gets really differentiating, the Harvard
path. That's what sets him apart. He studies
history and literature there, graduates 2004,
cum laude. Right. And he wasn't just dabbling.
He specialized in Russian lit and British lit.
And the really crucial part, his senior thesis
was on Vladimir Nabokov. OK, that Nabokov detail,
that feels like the key to this whole thing,
doesn't it? Nabokov, you know, Lolita, famous
for incredibly complex language, structural tricks,
unreliable narrators, just layers of wordplay.
Exactly. Dazzling stuff. So if you spend years
dissecting that level of precision, that structural
irony. You're basically training yourself to
be the ultimate comedy writer. It's intellectual
boot camp for satire. You absolutely nailed it.
Nabokov demands that kind of analytical shirkness.
And while he's doing that, he's also the president
of the Harvard Lampoon. The legendary Lampoon.
Right. Think about that combo. High level literary
deconstruction here and over here, churning out
topical, often silly humor for the Lampoon. It's
the perfect storm of highbrow theory and immediate
practical comedy training. Which makes the next
bit, the scramble phase after college, almost
more relatable. You come out of Harvard, the
Bokoff thesis, Lampoon presidency. Right. And
then reality hits. Right. He worked for a bit
as a reporter and copy editor for the Staten
Island Advance. Back home? Yeah, talk about humbling.
From analyzing complex Russian novels to writing
for a Nickelodeon cartoon, he worked on a short
-lived show called Kappa Mikey. Ah, Kappa Mikey.
The show is, you know, you take the writing gigs
you can get to pay the bills, build up those
credits. But that groundwork, that training,
it must have paid off fast. Uh -huh. Because
the big pivot was sending a writing packet to
SNL. That rigor, that precision, it must have
jumped off the page. He got hired as a staff
writer in 2005. That's incredibly quick. Graduates
College 04, writing for SNL by 05. It really
is. And we can't skip that very human pre -fame
moment. Remember, he was on Weakest Link, the
college edition back in 2002. Oh, we forgot about
that. Yeah. He won like $5 ,250, decent for a
college kid. But he said later he didn't really
feel like he deserved the win. What does that
say? Maybe something about his own internal gauge
for achievement, like real accomplishment versus
just luck. Could be. It sort of fits with that
controlled, measured persona we see later. Yeah,
maybe. OK, let's shift gears then into the SNL
world. That's where he really becomes a defining
figure in modern late night. Starts as a staff
writer, 2005. And you got to remember, SNL is
just this relentless machine. 90 minutes live
every single week. Totally relentless. And watching
his climb through the writing ranks there, it
really speaks volumes about his work ethic, his
output, and honestly, his administrative skills.
The titles tell the story, right? Exactly. Staff
writer, you submit jokes, sketches, then writing
supervisor, which he was from 2009 to 2012. That's
more like an editor, a gatekeeper. You're shaping
sketches, managing younger writers. That takes
more than just being funny. You need structure,
tiny skills. He probably sharpened studying literature.
No doubt. Then he gets bumped up to co -head
writer, 2012 to 2015. Now, for anyone listening
who doesn't know the SNL hierarchy, head writer,
co -head writer, that's like being the show's
general manager, it's a political compass almost.
Right. Setting the tone, overseeing everything,
managing the whole writer's room. Plus. Dealing
with pressure from the network, from Lorne Michaels.
Huge administrative weight. He actually stepped
back from it for a bit, but they clearly relied
on him. He came back as co -head writer, this
time with Michael Che, his eventual update partner.
OK. And that was from 2017 right up until 2022.
Just think about that period. He was steering
the ship, comedically speaking, for the most
relevant hour of political comedy on TV. Right
through the Trump years. Exactly. The super volatile
Trump presidency, the start of the Biden years.
That takes. incredible political awareness and,
frankly, a knack for neutrality. And you mentioned
his collaboration with Rob Klein, another writer.
They work together a lot. When you see that kind
of long -term partnership in a place like SNL,
it's just real trust. Finding someone who gets
your wavelength in that pressure cooker. That's
gold. Absolutely priceless. But the big shift,
the one the audience really saw, was the move
to weekend update. Summer break after the 2012
-13 season, Lorne Michaels taps him, asks him
to take over the desk, replacing Seth Meyers,
who was leaving for his own show. Wow. That's
the moment he goes from the back room to center
stage. Totally. It was a huge show of faith.
And he took it, debuted March 1st, 2014, initially
with Cecily Strong, but then pretty quickly settled
into that long -running partnership with Michael
J. And that chi partnership became so iconic,
didn't it? Because of that sharp contrast, that
intellectual back and forth between them. It
really did. And that contrast, that chemistry,
it led straight to the record books. October
23, 2021, that's when Just officially broke Seth
Meyers' record. Longest serving anchor in update
history. Think about anchoring that desk through
eight years. Latter Obama years, all of Trump.
Yeah. Start of Biden. That's just monumental
endurance, comedically and politically. For sure.
And he managed that longevity, I think, by keeping
that delivery really dry, objective, almost like
a journalist sometimes. It provided the stable
anchor point against Chess, you know, more pointed,
challenging style. It makes you wonder about
his influences. He's mentioned Norm MacDonald
as a big one for his update work. Said Norm's
tone was the one he grew up with. Also mentioned
Tina Fey. Is it weird that he cites Norm MacDonald?
Because Norm was much darker, riskier, kind of
surreal sometimes. Just seems so much more controlled.
That's a really good question. I don't think
it's contradictory, actually. I think it's maybe
a blend. Tina Fey brings the super sharp political
writing, the joke efficiency, that's the Harvard
precision, maybe. But Norm MacDonald, he provides
that model for the detached deadpan delivery.
That willingness to just let the absurdity of
the news hang there. Which you need when the
headlines themselves are so polarized. Ah, okay.
So, Jost takes Norm's tone but applies Kina Faye's
focus. That's how I see it, yeah. That makes
sense. Gotcha. And while he was mostly writing
and anchoring, he did do some character stuff
too, right? Brief cameos? Like playing Ohio Governor
John Kasich in a debate sketch? Oh, yeah. And
the super meta one playing his actual friend
and Harvard doormate, Pete Buttigieg, during
the 2020 primaries. Right. That works on so many
levels. The comedian playing his real life buddy
who's now running for president. Exactly. And
he did NFL Commissioner Roger Goodell, too, during
the 2021 season. So, yeah, even with all the
writing and anchoring, he could still jump in,
play a part, understood the ensemble thing. OK,
so we've got the definitive SNL chapter covered.
But Jost has been really smart about. building
his brand way beyond that building, beyond Studio
8H. Let's talk about his other work, starting
with stand -up. That's a whole different beast.
It really is. And trying to keep a stand -up
career going while you're also headwriting and
anchoring SNL, that's an insane juggling act.
Seriously. But he did it. He performed on Late
Night with Jimmy Fallon, TBS, HBO. And that's
important, right? It shows his jokes work outside
the update desk format, without cue cards, in
front of a live crowd expecting laughs now. And
he got that early industry nod, too. He was picked
as a new face at the Montreal Just for Laughs
Festival in 2009. Huge deal for a comic. Yeah.
And he kept doing Montreal, did the Chicago Festival,
too, for a few years after that. So that suggests
he was building a real independent voice as a
performer. Separate from just being an SNL writer.
Definitely. And then moving off the stage, his
writing the literary stuff that's really core
to his whole intellectual brand. He's published
four Shouts and Murmurs pieces in The New Yorker.
Which, for people who don't know, Shouts and
Murmurs is like the gold standard for short,
smart literary humor. Getting published there
is a big marker of sophistication in comedy.
Absolutely. Pieces like Explaining Your Time
Warner Bill or I Will Slap You. It shows that
high level wit. And publishing in The New Yorker,
New York Times Magazine, Huffington Post, even
back at the Staten Island Advance. It shows he
can adapt his satirical voice for different places,
different kinds of readers. Very versatile. And
then, of course, the big one for a lot of people
was his memoir, A Very Punchable Face, came out
July 2020. Right. That did really well. It did.
It seemed like people responded to the vulnerability,
the self -deprecation maybe. It let people connect
with him personally beyond the SNL persona. And
hitting the New York Times bestseller list, that
cemented him as a marketable author, not just,
you know, an SNL guy. Okay, let's talk hosting
gigs. Because this seems like a clear strategy,
positioning him as more of a mainstream media
figure now. Co -hosting the Emmys with Michael
Che back in 2018. High profile, high pressure.
You've got to appeal broadly, keep the show moving.
It's an administrative task as much as a comedy
one. And then the ultimate tightrope act, hosting
the White House Correspondents Dinner, April
2024. Oof. Yeah. That's the job where you have
to race the most powerful people in the room,
including the president, right to their faces.
While also kind of celebrating unity in the fruit
press. It's a crazy balancing act. Totally. His
monologue there, it's interesting. About 20 minutes,
he roasted Trump. He roasted Biden. Kept that
expected impartiality. But he did throw in a
line supporting Biden's decency. Which is a calculated
move in that room. Yeah. A bit of a risk. He
also joked about being married to Scarlett Johansson,
did the requisite joke celebrating the press.
That performance, I think it really cemented
him as the kind of satirist the establishment
is comfortable with. Sharp, but professional,
palatable. It's an endorsement of that controlled
intellectual style he has. In looking ahead.
That announcement, July 31st, 2024, he's hosting
Pop Culture Jeopardy on Amazon Prime Video. That
feels like the clearest signal yet of him diversifying.
It really does. I want to pause on that. Hosting
Pop Culture Jeopardy. Is that just smart? brand
extension, or is it maybe a step away from the
political stuff that made him famous? It feels
like a big move towards being a mainstream host
playing to a much wider audience that isn't necessarily
tuning in for political takes. I think it looks
very strategic. It leverages the persona he's
already built, smart, quick, composed, but puts
it in a safe, non -political format that could
run for a long time. It's a high -profile pivot
that really cashes in on the celebrity status
he built at SNL. Very savvy. Okay. If we're talking
unexpected moves, though, we absolutely have
to talk about the weirder stuff. Film work and,
yes, professional wrestling. Right. Okay, film
first. He wrote the screenplay for Staten Island
Summer back in 2015 and had a small part in it,
too. Played Officer Greg Callahan. He was also
in How to Be Single in 2016, minor role. And
he's kept acting a bit, sometimes mixing it with
his personal life, like having a cameo in Fly
Me to the Moon last year, which starred his wife,
Scarlett Johansson. Right. Supportive husband
move. And he's got a voice role coming up, Mr.
Moon and the bad guys, too. So he's definitely
building out a little acting and screenwriting
sideline. But the story that just screams deep
dive absurdity has got to be the WWE thing. March
2019, Colin Jost and Michael Che show up on WWE's
Monday Night Raw as special correspondents for
WrestleMania 35. Oh, my God. Yes. What were arguably
the two leading political satirists in America.
doing anywhere near a wrestling ring. What's
amazing is how fully they committed to the bit.
They didn't just observe from the sidelines.
No, they got pulled into a whole storyline with
Braun Strowman, this absolute monster of a wrestler.
Okay. And it ended with both of them, Jost and
Che, being surprise entrants in the Andre the
Giant Memorial Battle Royal at WrestleMania itself.
They're kidding. They were in the match. They
were. And the sources say their brilliant strategy
was to hide under the ring for most of it. Classic
comedy survival move. Avoid the giants. Totally.
But eventually they had to come out and they
made this one doomed attempt to try and eliminate
Stroman together. And here's the perfect Jost
moment. He tries to reason with Stroman by bringing
up his therapist. No, he tried to use therapy
talk on Braun Stroman. He did. It's the absolute
peak Jost persona applying that sort of Harvard
educated analytical approach to a guy who throws
people for a living. How did that go over? About
how you'd expect. Strowman immediately chokeslammed
him, then tossed both Jost and Che out of the
ring like nothing. End of story. Oh, man. Proof
that dry wit doesn't stop a chokeslam. Apparently
not. But it was just this perfect, bizarre, unforgettable
clash of worlds. Weekend update meets WWE. Hilarious.
Okay, let's shift to his personal life a bit.
There's some really interesting connections that
actually loop back to that intellectual start
we talked about. Like the fact that Jost and
Pete Buttigieg, former Secretary of Transportation
Pete Buttigieg, weren't just at Harvard. There
were dorm mates. Dorm mates in Leverett House.
That's wild. Isn't it? Sharing a dorm at the
start of their careers. And clearly they stayed
connected. Just donated to Buttigieg's mayoral
campaign back in 2015. And then, like we said,
he ends up playing Buttigieg on SNL during the
primaries. Yeah. It just highlights that small
interwoven world of the American elite connecting
politics and comedy. His biggest personal connection,
obviously, is his marriage to Scarlett Johansson.
Met when she was hosting SNL, which happens a
lot there. The classic SNL romance story. Right.
Started dating May 2017. Engaged May 2019. Got
married pretty quietly October 2020 at home in
New York. And they had their son in August 2021.
And that relationship undeniably boosted his
profile massively. Took him from being mainly
known by comedy fans to being a globally recognized
celebrity figure. And then there's the project
that's just pure quirky Staten Island love. The
ferry boat. Oh, yes, the ferry. In 2023, Justin
Pete Davidson, another Staten Island SNL guy,
they bought a decommissioned Staten Island ferry.
The MV John F. Kennedy. What are they even doing
with it? Well, it's partly just this giant amazing
inside joke, right? But it's also kind of an
investment. The sources mention it was actually
used in a movie last year called Screamboat.
Screamboat, okay. So it grounds them back in
their roots, gives them this very tangible, very
weird piece of local New York history. It's kind
of endearing. We've talked acting. But there
was a more recent kind of short -lived venture
into sports. He surfs, apparently. Yeah, he's
an avid surfer. Which led to this slightly odd
gig in 2024. NBC Sports sent him to Tahiti to
cover the surfing competition at the Summer Olympics.
A dry political comic covering surfing in Tahiti
for the Olympics. Why? I guess it speaks to how
celebrity works now. Networks want familiar faces
everywhere, maybe. But it raises questions about
juggling all these side hustles. Because his
time there ended abruptly. Oh, really? Yeah,
he left before the competition finished. The
sources just said it was due to multiple health
issues. Kind of vague. Huh. Just a little reminder,
I guess, that even super successful people have
limits. Not every gig works out perfectly. Exactly.
Even for a pro. Okay, let's wrap this deep dive
up by looking at the hardware, the awards, the
honors, the proof of impact. You don't get to
be the longest running update anchor without
racking up some serious recognition. Oh, absolutely.
Colin Jost has been an awards magnet. 19 Emmy
nominations total for his SNL work. That's a
cross -writing. The show itself is a variety
series. And now even hosting, he got nominated
for Outstanding Host for a game show in 2025
for Pop Culture Jeopardy. 19 nominations. That's
just sustained excellence over... decades across
different roles it really is and he's one too
he's a two -time primetime emmy winner and what's
cool is his recent wins in 2025 were for the
snl 50th anniversary special ah for the big anniversary
show yeah one for outstanding writing for a variety
special and for outstanding variety special live
it really shows his influence spanning his whole
career arc from a young writer contributing week
to week to being a key figure in celebrating
the show's massive history And beyond the Emmys,
the writers themselves have recognized him consistently.
Multiple Writers Guild of America awards. Yep.
WGA wins for Comedy Variety Sketch Series in
2007, 2009, 2010, 2017, 2018. Those WGA awards
are huge. They mean the people actually doing
the writing respect your craft. That's validation
from your peers. And then bringing it right back
home. full circle to Staten Island and academia.
He got an Honorary Doctor of Humane Letters from
the College of Staten Island, CUNY, in 2025.
That's fantastic. Yeah, recognizing his work
in comedy, TV, and community service. It's a
nice way to tie his celebrity status back to
his local roots in civic contribution. It really
is a remarkable story, blending that high -level
intellectual start with huge success in mainstream
entertainment. So if you step back and look at
Colin Joust's whole journey... It's pretty amazing
from that super intellectual background writing
about Mbokov at Harvard to becoming this incredibly
steady, dominant figure in modern comedy, holding
that weekend update record. Yeah, the key takeaway
for me is really about the power of applying
intellectual rigor to mass media. Just took that
deep academic training history. literature structure
and used it to become this really effective satirist
of American culture, politics, everything. He
managed to take the kind of precision needed
for Nabokov and make it work on the biggest,
most accessible comedy stage there is. Building
that bridge, making smart humor work in a broad
format. That's his real genius, I think. So we've
seen his success in writing, acting, hosting
these big events. The memoir did well. Now he's
got Pop Culture Jeopardy lined up, which feels
like a long -term play. Given all that, where
does his legacy ultimately lie? Is that weekend
update record the thing that defines him the
ultimate comedy writer and satirist? Yeah. Or
is that just the launching pad to becoming more
of a pure media personality, a mogul even? That's
the big question, isn't it? Yeah. You have to
wonder, how does that shift reflect where...
comedy celebrity is going right now does the
smart political satirist eventually have to soften
the edges move away from the controversy to achieve
that broader maybe less volatile mainstream success
something for you to think about as we see what
he does next