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April 9, 2024 26 mins

This week, Tommy is joined by actor Skylar Astin, best known for his star-making role as Jesse in the hit Pitch Perfect franchise. Skylar has so many incredible credits to his name, but today we are talking about one show that millions of people are tuning into each week and for good reason. He currently stars in the hit CBS show, So Help Me Todd. Skylar stars as Todd, a directionless but talented private investigator who works alongside his mom (played by the brilliant Marcia Gay Harden), at her successful law firm. Today, he opens up about what its really like starring in a fast-paced dramedy, what’s coming down the line for the rest of Season 2, how he worked his singing into the series in an unexpected way, how the projects that turned him into a household name will forever hold a special place in his heart, the importance of living his life with gratitude and remaining humble in Hollywood, why he will never tell someone they can’t do something, and how his cast felt like “The Beatles of 49th street” during his Spring Awakening days. 

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Episode Transcript

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Speaker 1 (00:01):
Hey guys, welcome to I've never said this before with
me Tommy di Dario. Today's guest is an actor who
has conquered the stage and the screen and who has
been making a smile for quite some time now. Joining
me today is actor Skyler Aston, who is perhaps best
known for his starmaking role as Jesse in the hit
Pitch Perfect franchise. And as a side note, if you

have never heard his rendition of since You've been Gone
from Pitch Perfect, just go download it and all I
will say is you are welcome. Skyler has so many
incredible credits to his name, but today we are talking
about one show that multi multi millions of people are
tuning into each week, and for good reason. He currently
stars on the hit CBS show So Help Me Todd.

Season two is out now, and this series is a
must watch. It is so relatable, especially because I'm an
Italian from New Jersey and I come from a family
where we have very, very funny things that have happened
throughout the course of my life. Skyler stars as Todd.
He's a direction but talented private investigator and he works
alongside his mom, played by the brilliant Marcia Gay Harden

at her successful law firm. So today we celebrate his
show So help Me Todd, and Skyler gives a little
hint as to what's coming down the line for the
rest of season two. I also really needed to know
what it's like pretending to sing badly when you really
are gifted with an incredible singing voice, which is a
moment that happens in season two. We celebrate some fan
favorite past credits, and then we go deep man. We

chat about how he leads his life with gratitude even
when doubt creeps in, how he keeps a humble mind
when he's receiving a lot of praise and attention, and
let me tell you his mentality on the importance of
encouraging his peers and a world's full of people that well,
quite often don't. It's really beautiful. So let's see if
today we can get Skyler to say something that he

has never said before. Now, Skyler, my man, how you
doing today. I'm doing, Tommy, I'm doing fantastic. I feel
like it's been a whirlwind for you lately. You hanging
in there?

Speaker 2 (02:04):
Yeah, yeah, I live for this. I mean like I'm
right now on set filming and I'm kind of in
between scenes right now, but I love burning the candle
to both ends. And when you're on a TV schedule
like this, this is when you get to talk about
the show and kind of about like how you're doing
and check in. So I make sure that all of
my check ins are on air and with people like yourself.

Speaker 1 (02:24):
Wait a minute, so you're actually filming the show two day,
like you're in between takes?

Speaker 2 (02:28):
Correct, not quite takes, but in between scenes for sure? Yeah?

Speaker 1 (02:32):
How do you do that? That doesn't mess you up?
I feel like i'd have to be like in my trailer,
we're going over my lines, ready to rock.

Speaker 2 (02:39):
You know, I've learned a lot that, like with TV
and how it works, you kind of have to be malleable.
I mean there are some times where it rains and
now we're changing the scene order or you know, something
like that, and you know, I try to protect myself
as much as possible and be as prepared as possible.
But when you're lucky enough to be in every scene
like I am, you know, you kind of have to

budget your brain a bit, and sometimes you know, you're
I'm constantly working during lunch and learning, you know, next
half of the day's stuff, and our show prides itself
on being very chatty and you know, having a lot
of dialogue, so I kind of have to do a
lot of gymnastics. So this is actually a nice active

break for me.

Speaker 1 (03:22):
Oh good, almost meditative exactly. Well, of course, the show
you're referring to, so help me, Todd, it is Oh
my god, it is so much fun. It is thrilling.
The banter between you and Marcia is so so funny.
I mean, there's no other way to describe it. It's
so comical. And the show is just really well done.
It's always interesting to me when primetime shows come out

and you're like, all right, how's this one going to be?
And there's so much content out there, but this show
nails it. So what made you want to be a
part of it from the beginning?

Speaker 2 (03:52):
I think right from the get go, Like when I
read the pilot from page one, I just loved how
he spoke. I loved how he was like approaching, you know,
solving crimes kind of in unconventional way. It's a bit
of a black sheep in his family too, and a
bit of a disruptor. So he's like the one that
gets to comment on the case as it's happening, and

not that he doesn't take it seriously, but he's kind
of thinking outside the box. And I just love that.
I also just love like the razor sharp banter between
him and March's character, Margaret. I just thought there was
so much mileage there, and I thought it was really funny.
I mean, it was initially built as a drama before
you know, we were able to finally admit that it
is a dramedy. But I just knew that Todd is

whether or not this is a drama, a DRAMAEDI a
comedy whatever. He is funny and he's physical, unorthodox. That
really attracted me to the character.

Speaker 1 (04:45):
Are you somebody who in real life likes to give
good banter? Do you give good banter?

Speaker 2 (04:49):
I got a sharp wit. I'm a little quick on
the uptake. I've been told depending on how comfortable I
am with the person. But yeah, yeah, I'm fast with
my reflexes for sure.

Speaker 1 (04:58):
Well, of course, you play a I've an investigator a PI.
Has that been a world you always wanted to explore?
Were you ever intrigued by that growing up? Or it's
just all totally new for you.

Speaker 2 (05:08):
You know, I love things like Inspector Gadget growing up,
I thought that that was like I always love those
kind of Dick Tracy's and even Sherlock Holmes or Harriet
the Spies. I never knew that I would play one.
I mean, this kind of fell into my lap in
a way, and I just love like the musicality, even
though it's not a musical, but like the rhythm of

the dialogue. It felt like I could hear it when
I read it, and I could hear me doing it
when I read it. So I just understood it right away.
And Scott prendergassar creator, has like such an amazing way
of writing and communicating through his words, and so I
just I was super attracted to it.

Speaker 1 (05:46):
And the relationship between you and Marcia Geharden, who of
course plays your mother on the show, is so well done.
There's such great chemistry between the two of you. How
has it been really mapping out that relationship and establishing
that Was it easy? Was it a little harder in
the beginning? Do you have to find your groove? Like
how did that all come to be? Because it seems
pretty flawless to me.

Speaker 2 (06:07):
Yeah, I think we had instant chemistry for sure. I
just think that what we wanted to make sure of
in season one was that there was love underneath and
that there was warmth and vulnerability underneath, because if there's
just two people yelling at each other, there's kind of
no substance to it. So we wanted to layer that
in and really, you know, talk to the writers, not

that they weren't already going in that direction, but just
like even in these little moments, just to kind of
like pick up where we left off, because even though
we do have to start over at square one each episode,
being that it is kind of that procedural format, we
do want to kind of keep some of our biggest
wins intact when we approach the next scene. And of
course there can't be too much growth because if we're
just completely holding hands getting along the whole time, then

there's not enough kind of drama and conflict there. But
it's just kind of become their inherent dynamics. So we
just know them and we know that he would do
anything for us mom, but also he thinks she's doesn't
do anything right, and vice versa.

Speaker 1 (07:04):
Why do you think people have fallen in love with
this show in such a big way, because I mean,
I see people talking about it all the time. It
clearly is doing well. We're in the thick of season
two and it's something that has a lot of conversation
around it. So why do you think that is.

Speaker 2 (07:18):
I think there's like some inherent joy to the show
because it is a mother and son relationship, and so
so many people can relate to that, even if they
don't have a mother, Like I know so many people
who watch it with their father or fathers that watch
it with their sons. There's people like to watch it
with either friends or family because they just relate. I
have a friend who works with his mother and they're like,

this is literally us. But then have I know people
who are like I definitely would never work with my
mother and can't imagine it. But this show is so
funny because it's as if I do. And so people
are really able to kind of like put themselves in
the position of Todd or Margaret or Allison or somebody
in the family dynamic and either kind of play out

their real life or kind of imagine their real life.
And I think that has that kind of like physical
draw to it.

Speaker 1 (08:06):
Do you think you would have been able to work
so closely with one of your parents.

Speaker 2 (08:09):
You know, I like worship my parents and I love
them so much, so it's it's it would not be
the same show as this one. I just think I
could do no wrong in my mother's eyes. But I think, yes,
it would not come without its frustrations. And you know,
I think that I like to keep work separate. I
like to support them and they like to support me,
and I think that, you know, I I like to

keep it that way.

Speaker 1 (08:34):
Yeah. I come from a big Italian family, and I
don't think we anyone would be able to get an
a word edgewise.

Speaker 2 (08:39):
So that's exactly right. You Italian. We're very similar, a
lot of over talking, a lot of like no no no, no, no, no, no,
this is what we got to do. And it's like,
let me just you know, I get to kind of
know what I do and you get to know what
you do, and we'd love each other for that.

Speaker 1 (08:53):
One hundred percent. So season two, we're loving it. What
can we expect throughout the rest of the season, anything
you can share.

Speaker 2 (09:00):
Well, we have some incredible guest stars. We have Dean Winters,
we have Jennifer Lewis, Heather Morris has been on the show,
who's been spectacular. And then yeah, there's one episode in
particular I really love with Matthew Wilkes, who plays my
brother Lawrence on the show, and he actually employs me
to work on a case specifically for him. And it's

not a law firm case if you know our show,
Like I work at my mother's law firm as the
detective and investigator, but I now in season two, I'm
running my own boutique investigative firm outside of the office,
so this kind of falls in that category. And I
am working in the secrets with my brother and we
really get to explore that relationship and I just absolutely

love doing it. It was so funny. And then sneaks
up on you in the way that our show only
does and just really finds some beauty and never really
hits you over the head with its message, but we
get one in there, and I'm really excited about it.

Speaker 1 (09:56):
And something else that's been exciting is I know you've
talked about how you sing in this series, but in
a different kind of way, not in a way that
people would expect.

Speaker 2 (10:04):
Right exactly. I mean, I've definitely gotten to get some
Easter eggs in there if you're listening some jingles on
the AM radio stations. I've just written and done and
just sent, you know, emailed over to our post production
team and they kind of layer it in. But yeah,
there's a lot of like singing off screen, but when
Todd actually attempts to really sing as Todd, it doesn't

sound like myself.

Speaker 1 (10:27):
Is that hard for you to do?

Speaker 2 (10:29):
It's fun for me to do. I think it's a
little wink at the audience. There's actually one moment in
particular in episode five that's coming out in April, where
I it's an opera scene. So it's like a big
opera episode where at the opera and there's something that
happens at the opera, we have to explore it. So
there's a moment where Todd finds himself alone on the
stage and goes to belt out a note and let's
just say, it doesn't sound great.

Speaker 1 (10:51):
I don't know how you can make yourself sound bad.
That seems like that would be a little challenging.

Speaker 2 (10:56):
You know, if you know how to kind of hit
the notes, you also know how to fall just show
of them and kind of manipulated in that way.

Speaker 1 (11:03):
So what do you think is the best part about
being you know, in a sitcom in a dramedy like this.

Speaker 2 (11:09):
I just think, like all of the people that I
meet along the way, and I don't just mean like
the actors and actresses and crew members I come across,
but having new characters come in and how they kind
of relate to Todd and how they relate to Todd
and Margaret. I think that's like a really fun part
to perform. It keeps it fresh to me to have
the pace every week and then to also deep in

the character throughout the course of the seasons and the
series and have like some steady growth. But yeah, I
just love like kind of working with new directors too.
We have a nice roster and it's growing, you know,
and there's definitely people that are going to be coming
back and back for you know, hopefully seasons to come.
So I think it's kind of like making that little
core family. I absolutely adore our crew. They're so wonderful

and encouraging and so good at their jobs, and it
inspires me every day to you excel at mine.

Speaker 1 (12:00):
And that's always good moral on set, and I feel
like it makes artists do even better work because you
actually are enjoying yourself right totally.

Speaker 2 (12:07):
I mean everyone, you know, anytime I have like a
visitor come, whether it's family or friends come to set
and it's the first time ever in a film set,
they're always marveled at how many people and how many
things and departments you know, it takes to do this,
And I never lose sight of that. We can't do
this with any piece of the puzzle. Yes, we're very
front facing, being that we're the actors and that we're

on camera and we're on the posters and everything like that.
But you know, if it's not lit, if it's not recorded,
if it's not you know, miked, if it's there are
the props and the set design and the set decoration
and just everything you know that makes this such a machine,
it would fall apart. And so like everyone is equally
as important to this project as the next person.

Speaker 1 (12:55):
Well, good on you for having that gratitude, because that's
one of the many reasons, in my opinion, you've had
that's such a long and successful career up to this point.
I mean, you've been working as an artist now for
most of your life, between Broadway, between TV, between film,
so what would you say is one of the best
parts about what you do, and what would you say
is one of the more difficult parts.

Speaker 2 (13:17):
Man. First of all, I mean corny and typical, But
first thing that comes to mind is I'm living my dream.
I'm literally living my dream every day. Look what's the
most difficult, you know, working on no sleep and you know,
sometimes your brain is literally so exhausted at the end
of the day and all you want to do and
people go, oh, what are you gonna do for dinner?
You know, what are you gonna do tonight? When you

wrap and you're like prep the next day. Of course,
how the heck do you think I'm doing eight pages
a day and these you know, page long monologues. It's
it doesn't stop. But I asked for this, and you know,
I never lose sight of that. I want to have
a long career and I know what it takes. And
I also know that, like if I'm complaining, there's someone

to my left that has less of turnaround time, you know,
who doesn't get to have as cushy conditions as I
do on set, And you know, we're all in this together,
and so that kind of inspires me and keeps my
drive alive. But yeah, I think the best part. I
can't imagine doing anything else at this point. And I
really love to tell stories and I love to be

an escape for people, like especially on TV with this show,
with my previous shows that I've done. You know, what
I've heard a lot is like, you know, with everything
going on these days, I just love, you know, tuning
in to you guys who really brighten my day or
you've helped me breathe a certain loss, or you know,
really repaired my relationship with my own mother or whatever
it is like that is, I never lose sight of

how even though you know, it seemed like we're just
doing a fun, silly show, like it is important, like
this does have meaning and we are we are giving
people something that you know makes them feel comfortable and safe.

Speaker 1 (14:53):
I imagine even on your toughest of days, knowing that
keeps you going right, it keeps you.

Speaker 2 (14:59):
Motivated absolutely, and also just how lucky I am. I mean,
it's not just about the fan service, like I really know,
believe me, Like even though I've been doing most of
this most of my life, like it's not without it's
difficult moments where you know, you're out of work for
more time than you would prefer, and you start to
go when the hell am I ever going to work again?
And we're very lucky and we're very blessed to be

able to do this. I never lose sight of that,
and and it makes me work that much harder.

Speaker 1 (15:26):
Well, I'm glad you brought that up, because I think
a lot of the time, when people think of their
favorite artists, you know, it's the glamorous side. It's the work,
it's the movies, it's the films, it's the shows, it's
the awards and the red carpets and all of the things.
But to your point, there are lows, likely in any profession, right,
and there are bad days. We all have a bad day.
So how do you just kind of keep on going?
Are you somebody that's generally a pretty optimistic kind of guy?

Speaker 2 (15:50):
I think so. I mean, I try not to complain
because I know that the people you're complaining to, if
it's on set, like there are people like, well, I
hope you don't quit, because that would put me out
of it job. And you know what I mean, Like,
it's really a general perspective, and it's kind of how
I was raised there are so many more difficult and
challenging jobs than what I'm doing. So I also know that,

like starting out during theater, there was this interesting perspective
that it taught me. I was in this big hit
Broadway show and I awaken, yes, yes, shout out. But
when I and I was like the Beatles of forty
ninth Street, Like we would come out of that stage
door and people were tearing at our clothes and you know,
really people really connected on a deep level to that show.

And then I would walk up the street and no
one would know who I am, and that didn't disappoint me.
I just never relished in either of them. And I
think theater gives you that perspective of literally, you're famous
on this one street, and then you go home and
you take the same subway as everybody else, because you
know you're on that salary and you know people are

holding your playbill and you're kind of like, oh, yeah,
that's me on there. But here I am like, you know,
transferring with you, and I don't know that just the
fact that this could all kind of go away. I've
had shows and experiences where I thought we're going to
be a huge hit and then they ended up not
being a successful and vice versa, or shows that I
thought we're going to go the distance where I was
told would go the distance, and then for whatever reason,

they didn't continue. So I think like it's those kinds
of losses or disappointments that kind of make these moments
not only sweeter, but just give you perspective that this
could all go away, so you better like enjoy it
while you're doing it.

Speaker 1 (17:29):
By the way, I think we were on the same
age and I saw you in Spring Awakening. It was
one of the first, you know, collection of shows when
I started getting into theater, and I just remember being
blown away by that experience. It was like mind blowing
to watch that. It was so cool.

Speaker 2 (17:43):
Thank you. It was a lot to carry too, and
we talked about it. We did this amazing documentary for
HBO Max called Those You've Known, and it was like
this fifteen year retrospective on the show, and we also
did this fifteen year anniversary concert that they kind of
layer in. It was really well done. But what we
kind of all talked about was like it was a
lot to take on because we were that same age
as you carrying these really intense stories, and people really

felt like, you know, we were saving them in many ways.
I mean, I've had a lot of experiences where people
come up to me at the stage door and tell
me like, I was feeling a certain way in my
depression where I wanted to end it, and this show's saved.
You know, it's lots to take on, and it is
a privilege, but it's also you know, it's just a
lot when you're also do you don't have any separation

from that age and from that feeling yourself. And I
remember a lot of Broadway performers would tell me when
they would come backstage, they'd be like, Hey, this isn't
going to hit you the impact and the importance of
what you're doing for several years, maybe like ten, fifteen,
twenty years, And here I am, like year seventeen, being
like they could not have been more right. You know,
we're still all on the same group chat, and we

still all talk about not only just like the show
being performed in every country in the world, but just
kind of like what that all was and what that
meant and just funny stories and it's kind of it's
something that I carry with me so closely that experience specifically,
and even that I think informs what I'm doing today.

Speaker 1 (19:07):
Yeah, I can't imagine. And it's so cool when you
get to be a part of something that does mean
so much to so many people and who as a viewer,
as an audience member, will carry that with them for
the rest of their lives. And you got to do that.
What's Spring Awakening? You get to do that with a
lot in your life. I know a million people ask
you would you do another Pitch Perfect and you always
seem enthusiastic and say yes. So instead of that, what

would you want to see if you were to do
something related to that genre?

Speaker 2 (19:31):
Again, Like what kind of musical TV show or movie
would I like to take on? Absolutely I've said before
and like, thank you for doing your homework. I guess
you're like, well, everyone asks him this, and by the way,
that answer is true. I would do one. But I've
said before like a Billy Joel bilepick would be great.
But I think to like take on the life of

a musician performer, almost like one of those like inside
Lewin Davis movies that kind of broke out Oscar Isaac
or just something like I remember see like When I
saw Wonka with Timmy Shallomey, I was just like, not
like I want to be the next Wonka, but I
was definitely like, Wow, I'm so happy that this is happening,
because big musicals like this should be celebrated and should

be done. I think I have the skill set to
do one of these, and so I don't know, maybe
to tell like an original story. Maybe it's not you know,
a biopic or a remake, and it's just like an
original story where I get to really sink my teeth
into a role and do everything that I've grown to
be able to do, whether it's comedy, drama, emotion, but
also singing on camera and maybe even singing live on camera.

Speaker 1 (20:37):
Did you ever think you would be able to do
it all? I mean, between theater, film, TV, like to
check off all the boxes and conquer each medium like that.
That's pretty badass.

Speaker 2 (20:48):
I appreciate that. I honestly don't think I ever Really
It's not that I ever was like limiting myself. I
just think that I was just taking it a step
at a time. When I started doing theater, the dream
was to be on Broadway, and that was only dream.
And when I was on Broadway. I was like, great,
I just want to be in this community and stay
in this community and keep doing all the roles. And

then you know, I was lucky enough to put myself
on tape for a movie and then that happened, and
it's all kind of again like informed the next step.
And now when people ask me like, hey, what do
you prefer? What would you you know, if you could
pick one, I go, that's not even a reality for
me anymore. They all inform each other and I couldn't
part with either. I now like love what I love

about each medium, and I also embrace the challenges of
each medium, and that's why I like to kind of
sharpen my skills in either just to go back to
the other and excel at that one that much more.

Speaker 1 (21:41):
Well, that's a really cool way to approach your artistry,
and I think that's what keeps everything so fresh and
at the tip of your fingers for You're You're such
a joy to watch and it's really cool to see
you across all the different mediums and anything that you do,
which is awesome. So the name of the show is

I've never said this before, so I'm wondering, is there
something either silly or deep or whatever comes to mind
that you've never said before that you want to share
it today.

Speaker 2 (22:16):
The first thing that comes to mind, and I don't
mean this literally, is you can't do that. And obviously
I've said the words you can't do that. I mean,
if someone says, hey, I'm going to steal this gum
from this DELI, I'll be like, hey, you can't do that,
or you know, say this incredibly inappropriate thing that you
know should not be said. You can't do that. You
can't say that. But I think it's like when I

say that, when I'm like imagining, not saying that, I
feel like if somebody is trying to make some sort
of a positive change in their life, and even if
what they're saying is a bit, maybe in my own opinion,
deep down a bit unattainable for that person, I would
never ever want to be the person to limit someone's
potential or expectations for themselves. If someone said, hey, I

really you know, I've gotten sober and I really want
to get into singing and I really want to. I
think in three years, if I work every day, you
know I want to, I'll headline the met in ten
years you know, I wouldn't say you can't do that.
I mean, I might think, like I think you're highly
underestimating what it takes to get to that point, and

maybe I would even give some kind of friendly advice,
but it would be encouraging. And I just think that
like barbia from me, to ever tell someone something that
they can't do if they believe in themselves, and especially
if they're trying to again affect positive change in their life.
It's just not in my nature. And I just think
it says a lot about a person that would kind

of say that and doubt somebody. And I try not
to doubt people again, especially if what they're doing isn't
problematic or dangerous to them or dangerous to others.

Speaker 1 (23:53):
Oh, I love that. I mean to kind of recap that,
it's basically you're saying it's not your job to say
what someone should or should do. Of course, as a human,
you might have an opinion, but you also will probably
keep that to yourself and encourage someone to go after
what makes.

Speaker 2 (24:06):
Them happy exactly. That's exactly how I feel.

Speaker 1 (24:09):
That's pretty cool. Thank you for sharing that. I love that.
I think that's a good reminder we need more and
more in this overly opinionated world we live in, especially
due to social media. So I appreciate that totally.

Speaker 2 (24:20):
I think encouragement is something that is getting a little
lost these days, and I think people are constantly trying
to pick others apart and say what they can't do,
and I'd rather focus on what people can do. And
I think if we do give that encouragement to people,
they might even surprise us because who knows, maybe that
friend will headline the met in ten years. Maybe they'll
tap into something that I didn't know they could do
and they didn't know they could do. But I would

never want to be an obstacle for them to have
to overcome.

Speaker 1 (24:44):
Well, speaking of encouraging someone, I'm going to keep encouraging
you to doing the badass job you're doing on So
help me, Todd, because we love it. It's a show
prime Time hasn't needed. It is so much fun for
everybody listening. It is out now, so keep enjoying it
week after week. Skyler. I mean, just awesome. I really
enjoy the conversation. I appreciate you for coming on in
between your sets and your takes today. I appreciate you

hanging out.

Speaker 2 (25:07):
It's my pleasure. Honestly, you've made this an absolute joy
and a delight. You're a wonderful guy. Honestly, you brought
it all at me, so I really appreciate you having
me on the show.

Speaker 1 (25:16):
Oh, thank you, and wishing your continued success on the series.
And until we meet again, my friend.

Speaker 2 (25:21):
Definitely I will see you soon.

Speaker 1 (25:24):
I've Never Said This Before is hosted by Me, Tommy Dedario.
This podcast is executive produced by Andrew Publisi at iHeartRadio
and by Me Tommy, with editing by Joshua Colaudney. I've
Never Said This Before is part of the Elvis Duran
podcast Network on iHeart Podcasts. For more, rate review and
subscribe to our show and if you liked this episode,

tell your friends. Until next time, I'm Tommy de Dario.

Speaker 2 (26:00):
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