EXCLUSIVE: 'Insecure' Showrunner Prentice Penny Talks Season 2, Directing Issa Rae & Quashes 'SATC' Comparison

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HBO

Prentice Penny wears many hats -- showrunner, executive producer and writer -- on the HBO series Insecure, about two black women navigating work and relationships in South Los Angeles. And with Sunday’s episode -- season two’s “Hella LA”, which he calls a bridge between the first and second half of the season -- he’s added director to that collection.

After years of producing shows like Scrubs, Happy Endings and Brooklyn Nine-Nine, Penny has finally helmed an episode of TV, something he tells ET he’s wanted to do for a while now. But it was Insecure -- which was co-created by and stars Issa Rae -- that proved to be the best place for him to make his directorial debut. “It’s certainly a safe environment because I know the show and what we’re going to accomplish creatively,” Penny says. “The most interesting thing, which I’ve told Issa and other people, [is] it helped me see our show from a much clearer lens.”

MORE: It's Time for Issa Rae to Take a Bow, or at Least a Nap

There’s no doubt that season two, which has seen best friends Issa Dee (Rae) and Molly Carter’s (Yvonne Orji) worlds turned upside down by problems at work and a role reversal in their dating lives, has a clear goal to top a critically acclaimed first season -- but also to get more insular, Penny says. “For us, instead of trying to focus on how to be bigger and better, it was, ‘What if we could get smaller? Let’s actually focus more on nuances of the characters.’”

With that said, audiences have delved deeper into Issa’s insecurities, often through her mirror-facing soliloquies, and seen more of Molly’s life, particularly at work, where she faces an upward battle for equal appreciation.

In a chat with ET, Penny opens up about the show’s expanding world in season two, addresses concerns about becoming the black Sex and the City and if, like Tasha (Dominique Perry), he thinks Lawrence (Jay Ellis) is a f**kboy. 

ET: Even though Insecure is meant to be about two best
friends, season one was largely focused on Issa. This season, audiences have
gotten to see a lot more of Molly and her perspective. Was that a conscious
decision going into season two, to make sure the narrative was about both
characters?

Prentice Penny: Like
any new show, when you have a character, Issa, who is the lead of our show,
every story is funneled through that lens. Even the Lawrence stuff, everything
is through her; you sort of know everybody tangentially through her. Now that
you know the other characters, you can start to say, “Well, how do you expand
their world? How do you explain the things that they're going through and
things that they're feeling and the things that they're living?” Last year, we
got really focused on the dating faults that Molly has, [but] she's a character
in our show -- the only character who's an African American person in a very
corporate environment. Lawrence obviously lives in the tech world and Issa has
her own experiences as a person of color in this nonprofit, but Molly can't
just be a woman that we're just funneling dating stories through. She’s a
lawyer. My wife is a former attorney, my mom is an attorney. At the end of last
year, Molly had this awakening about how she has treated men and how she views men
in her life; and so, obviously, going through therapy, we wanted to be true to
a character who wants to step away from that in a way. Then for us, it was like,
“What's the one thing that has been consistent for Molly? It’s her work life.” We
wanted to dive in and address those things.

While the group
scenes with Issa, Molly, Kelli (Natasha Rothwell) and Tiffany (Amanda Seales)
can be a lot of fun, there has been some concern among viewers that it feels
too much like a black Sex and the City.
Is that accurate at all?

What Sex and the City
would do is have four individual story lines and they would come in and out. I
don’t think we’ll ever follow Kelli’s dating story, you know what I’m saying? I
don’t think we’ll follow a Tiffany and [her husband] Derek [Wade Allain-Marcus]
life story. For us, that’s never going to be a thing. How we use [Kelli and
Tiffany] are as sounding boards and other POVs that our two main characters -- and
certainly Issa -- are bouncing things off of. There’s no conservative effort to
make all of them be an ensemble piece.

Since you and Issa
work closely together on the show, how was it directing her?

It was seamless in a lot of ways, because, you know, in
television, even though you're not directing, you're there by the camera
certainly saying, “Hey, let's get her to do it more like this.” Because even
when she's not on camera, she trusts me to make sure that she's delivering what
we're supposedly setting up. That part felt very seamless because it's kind of
what I do anyway. 

MORE: Yvonne Orji Dishes on Sterling K. Brown's 'Insecure' Role

How did you end up
directing “Hella LA”; was that by choice?

No. Weirdly, it kind of ended up in my lap. I almost didn't
want this episode because of the scope and the scale of it. It’s the only
episode of our show that takes place in one day. There's a giant threesome.
There's a huge club scene that takes up 80 percent of the episode with 300
extras. You know, for me, I really wanted to do something like episode three or
episode five that's a little bit smaller. Melina [Matsoukas] was directing the
first two and the finale, and I was sitting there like, “Well, I guess I'm
taking this one.” But I was glad I did. If you're not excited and scared, then
there's nothing to really push you or challenge you. Because this episode scared
me and because I never wanted those club scenes … I think it helped push me and
challenged me. I’m very proud of how it turned out.

Considering
Lawrence’s threesome and what happened last week, when Tasha called him a
f**kboy, I was curious if you think Lawrence is one.

In the pilot he starts off in such a negative place right?
We had to spend so much time trying to get people to care about him. So we had
to get people to invest in this relationship. By the end of the first season there
are all these conversations [about whether] Lawrence is a good guy or not a
good guy. So we really wanted to address that, so we pull away at that and chip
away at a guy who's hurt and acting out. For us, we’re playing in the grey. Nobody’s
all one thing, nobody's all good. [Issa and Lawrence] are both acting out,
they're both hurt. They don't have closure on a life journey that was five
years in the making. So they're both acting out in ways that are kind of out of
character. We really wanted to address all the guys out there who watch the
show [and] are like, “This is the best,” and all these women out there saying,
“Had he not done what he did he wouldn't even be here.” We wanted to address
both of those sides and say he's not all one thing or the other.

How did the show land
Sterling K. Brown as a potential love interest for Molly? 

Sterling was just a fan of the show. Issa said he reached
out to her and said, “Hey, I love the show. I would love to be involved in the
show some way, if that's possible.” And we were just like, “Yes, we'll make it
possible.” He came in -- at that point it was pretty late in the process -- and
we’re trying to figure out who does he become, who is he and then we have the
character of Lionel, who became a very interesting dynamic [for Molly]. What I
like, if you watch enough sitcom tropes, is you think, “I know where this is
going.” And for us to take you to a different place, I think that's where Molly
is like, “That's what I used to look like. I don't want that.” Last season she
would have jumped on this guy who is ready to settle down. He has all his stuff
together and is talking about family, that was everything Molly wanted last
year. And now it doesn't feel right. So here’s a character making a choice
about her personal growth that's counter to what she's been doing, and that's
kind of a nice moment for her. 

HBO

Will we get to see
any more of Sterling?

You know I can’t tell you that!

What I also find
interesting this season is how the show is addressing Donald Trump. A lot of
shows have addressed him in different ways, but here it’s seen through Issa’s
job. Was there a conscious decision made about bringing that reality into the
world of Insecure?

It’s part of the real world, just the same way that Obama
was influential in the show. The world we currently live in has drastically
changed from when the show was shot in the first season to the show we're doing
now. We never wanted to name him -- that’s not really our show, like, that's
something SNL does great. We'll leave
that to them. Our show is about Issa and the people who live there. We want it
to be true to the climate that we're living in, but again, our show is about
Molly and Lawrence and it's not about that, per se. So in doing that, we can
touch on a few of those things without having to say Trump this and Trump that.

The other great thing
about season two that everyone has been talking about is Due North, the show-within-a-show starring Regina Hall and Scott
Foley. Will we continue to see more of that and is that story line going
anywhere?

We’re building to the finale. Last year, we had a fake show,
Conjugal Visits, and this year we
liked the idea that there’s always going to be a show in our show… HBO was kind
enough to let us [do it]. We had written 12 one-page episodes of Due North that had so many twists. At one
point there was a slave brunch scene that was going to happen, and then they
were like, “We don't have money to do that. You can't hire 300 slave extras for
a show-within-a-show.” So we whittled it down to eight minutes, essentially,
and shot -- our director Pete Chatmon was amazing -- and we basically shot
eight episodes.

MORE: Issa Stumbles Through Single Life, Molly Scores a New Man -- 'Insecure' Recap

Considering episode
four marks the halfway point in the season, who should we be paying attention
to as we build toward the season two finale?

People should be paying attention to the things that are
coming down the pipeline for everybody’s relationship stuff. That’s definitely
going to kick up a notch. Lawrence is dealing with the fallout of him and Tasha
and what it’s like to be a single black man. He’s like a unicorn: no kids, a college degree and stable money. The
same with Molly in being an eligible single black woman out there that seemingly
has her stuff together. It’s definitely building to a head again and again. You
know Molly doesn't have any more closure for her experience; she's not going to
therapy. She's hurting. Lawrence and Issa have yet to have a talk since episode
one ended, and that wasn't even a talk. They haven't really spoken about how
they ended things since season one’s episode seven, after they had their blow-up.
Again, you have a lot of people in the show who are still hurting and haven't
had a chance to get all that out.

I don't want to give too much away, but I think it's always
the person you're not checking for or the people that might be hanging around. We
try to do that, where you're going to see something in episode two that you
don't even realize is going to be a thing until episode six. Without giving too
much away, I think that thematically you'll see a lot of people who'll have
their feelings bubble to the surface and finally things kind of come to a head.

You wrote episode
seven this year. What can we look forward to from that?

I wrote episode seven last year as well. I love that the penultimate
episode always has this -- for the last two years of our show -- has these days
building like a pimple about to pop. It’s all building to a moment. I love
uncomfortableness in shows and things that make you cringe, so there are a lot
of cringe[-worthy] and uncomfortably awkward moments in that episode. Imagine all
the people in our show in a room at one moment and you might get a sense of how
things might feel.

Insecure airs Sundays at 10:30 p.m. ET on HBO.