“‘Am I going to be okay?’
is a huge theme for really all of the characters this year,” showrunner Prentice Penny tells EW.
(Note: Some of these quotes also appeared in EW’s recentInsecuredigital cover story.)

Issa Rae and Yvonne on ‘Insecure’ (inset: Prentice Penny).Raymond Liu/HBO; Kevin Winter/Getty Images
ENTERTAINMENT WEEKLY: What are you most proud of when you look back atInsecure’s journey?
That is something I’m super, super proud of in the legacy of the show.
We were like, “But what do we have for the end?”

Natasha Rothwell, Yvonne Orji, Issa Rae, Amanda Seales, and Wade Allain-Marcus on ‘Insecure’.Raymond Liu/HBO
“You’ll figure it out.”
That was the most interesting stuff, and we were kind of stalling the story.
What sparked the most debate in the room?

Issa Rae and Jay Ellis on ‘Insecure’.Merie W. Wallace/HBO
One of our EPs, Amy Aniobi, was like, “Oh, hell no.
She can’t say that to her.
It was around episode 6 and 7 when we were having these arguments.
Was there ever something you discovered organically that changed the course of the series?
Same with us casting [consulting producer Natasha Rothwell].
She was never intended to be Kelli; she was there to write.
But when she would read Kelli at our table reads, we were always laughing.
We just gave her the part.
We never brought anybody else in.
Insecurehas a very vocal fan base.
What has been the most surprising fan reaction?
I was surprised that people had a lot of Molly hate in season 4.
But it was definitely more 70/30, people mad at Molly than Issa.
[Fans were] like, “Oh my God, that’s not Derek’s baby!
Simone is not Derek’s baby.”
It’s just like, “No, that’s his baby.
We’ve done nothing.”
How did you settle on five being it?
I think we both said it at the same time.
We were like, “How long do you want to do the show for?
Look, we’ll say our answer on the count of three,” and we both said five.
It felt like the right amount of time to do a show.
We could have been way off, who knows?
I’m still leaving when people still want us around.
We always looked at our show as, “It isn’t meant to be 90 episodes.”
I think we just felt that’s the right amount of time to tell these characters' stories.
Coming into season 5, did you look to past shows for the dos and don’ts of final seasons?
A show that we looked towards wasSix Feet Under.
We thought that their finale was really strong.
That was the barometer we used, because initially we put a lot of pressure on ourselves.
One day Amy said, “We got to stop thinking about it like [that].”
We had to think of these characters' lives will continue.
It’s just the writers are jumping out of the plane.
Then let’s end season 5 that way.
How would you tease what to expect from the final season?
Which is what we all want to know.
Am I going to be okay if this friendship goes away?”
Can you find a way to be happy?
Can you find a way to still thrive?
What do you hope the legacy of the show is?
I guess I hope the legacy of this show…
I don’t know.
I feel like legacy is always for other people to figure out.
When you’re in it, you’re not trying to think about legacy.
So growing up, I was a huge fan ofThe Cosby Show.
My mom was a lawyer, my mom was an AKA like Clair Huxtable was.
My best friend’s dad was a doctor.
My dad did real estate and had his own business.
That is possible, so let me do it for my show."