How to Stay Black and Still Win In Hollywood, According to Director Prentice Penny

How to Stay Black and Still Win In Hollywood, According to Director Prentice Penny

The ‘Insecure’ showrunner shares his keys to success

Photo illustration. Source: Getty / Bonchai Wedmakawand / Emma McIntyre / Staff

Writer, producer, and director Prentice Penny has spent his entire career making the best out of every situation — even though his break was a pretty damn good one.

Penny, 45, cut his teeth in the writers’ room of Girlfriends, an archetype of network sitcom longevity in the 2000s. He didn’t take being surrounded by other Black creatives for granted, especially after the Writers Guild of America strike that crippled the 2007–08 television season became a death knell for Black shows like the aforementioned. Penny found work on Scrubs, the cult hit Happy Endings, and Brooklyn Nine-Nine, but from the finale of Girlfriends up until Insecure came into fruition in 2015, he was the lone Black person in every writers’ room in which he was employed.

Penny’s upbringing prepared him to be an outlier. He grew up in Los Angeles’ Windsor Hills neighborhood and went to summer camp with White kids in the Valley and Malibu before enrolling in University of Southern California’s screenwriting program. When he was hired as Insecure’s showrunner, Penny was adamant about doing what he learned to do throughout his career: Looking out for other Black people.

Now that Penny has solidified his spot in Hollywood, he’s committed to telling the type of stories he wants to tell. His first feature film, Uncorked, is about a young man balancing his dream of becoming a sommelier with his father’s expectations that he’ll take over the family business. “Often when you see a [Black] father-son story, the father being absent is at the spine of it,” Penny says of the film, which hits Netflix today (March 27). “That wasn’t my life or a lot of my friends’ lives — we had very active Black fathers. I wanted to write a movie about how Black men communicate.”

“‘Insecure’ wasn’t something people were thinking would be the thing; it was just something I really believed in. It taught me to pick projects based on what you feel, not what you think is going to be the easiest path to get somewhere.”

There’s no formula for “making it” in Hollywood, but ahead of Uncorked’s release and the premiere of Insecure’s fourth season next month, Penny dialed up LEVEL to discuss how to navigate the ascent — and bring others up the mountain with you — in his own words.

Put in the work

Work at your craft daily. When I was coming up, to make a movie you had to buy film, process it, get it developed, then transfer it to video. It was super costly. Now you can shoot a movie on your phone, edit it on your phone, then post it so people can see it from their phone. Literally every step can be from your phone. So unless you’re studying, practicing your craft, and working as hard as you can, you’re kind of wasting your time.

Be ready to keep it movin’

I don’t think anybody feels like their show is gonna go on forever, unless you’re on a show on CBS, NBC, or ABC, like Law & Order: SVU or NCIS. Most people now are like, “I’m gonna do 12 episodes of this show, six episodes of this show, and that’s my season.” You’re able to develop quicker because you have so many platforms that need content. Every network has a streaming platform on top of things like Quibi or the cable networks and their streaming outlets. Shows are three seasons now, and then you’re done. You need to have four or five things in the fire because the traditional structure is antiquated.

Master your formula — but continue evolving

I love hip-hop, but I hate when an artist repeats their formula. Like, if I have this album, then why do I need that album? They sound the same. I equate that to the way we do our shows. I want each season of [Insecure] to feel like our show, but I don’t want you to watch season two and think you know exactly what season four is going to be about — because you don’t. We’ve tried to give each season its own theme and grow the characters. There’s still Issa and Molly, Lawrence, their people. But they’ve grown, and we have to acknowledge that as we develop the season. They can’t be doing the same things they did before; it would be silly. It’s not like a network show where Joey on Friends is always going to be Joey, no matter how old he is. Now, especially on cable, you can be more nuanced and evolve that character. Issa’s always Issa, but she doesn’t make the same mistakes and is aware of things now — or doesn’t want to repeat the same mistakes and can acknowledge that. Every season, we try to build on the last and say, based on the things we’ve set up, where would that character be six months later?

Trust your gut

Right before Insecure, I had two other pilots: One at FX and another at NBC with Bruno Mars. Those projects were good to do, but I got fired from one and the other never went anywhere. My confidence was really shaken — for the longest time, I was trying to dissect where it went south. The problem was that, in my spirit, I felt like Insecure was right and those things, while cool, weren’t right. Insecure wasn’t something people were thinking would be the thing; it was just something I really believed in. It taught me to pick projects based on what you feel, not what you think is going to be the easiest path to get somewhere.

That stuck with me, so everything I do now, I go off instinct: Is this something I’m instinctually interested in? I don’t really care what the pieces are that get it there; I just care about whether I’m into it or not. That has to be the fundamental question regardless because you’ve got to sell it and live it. If you can’t sell it because you don’t believe in it, then what’s the point? Since then, I haven’t tried to work on anything that I don’t 100% get or comprehend how I can improve.

Move smart

You have to network laterally. Issa [Rae] and I have talked about this a lot. Being a young person in your craft and getting to me is not an achievable goal. And I can’t necessarily help you. I have a million other things I’m working on and trying to do. If I took every person’s idea who just wants to sit down with me for coffee for 15 minutes, I would never get any work done. And not that I’m not thankful — I know what it’s like to be on that side — but when I think about the people who helped me as I came up, it was all my friends in film school. We were reading each other’s stuff, helping each other, then this person got a thing, then that person helped me get a thing, and we were kind of moving laterally. All my stuff came that way, it never came from getting to the top person.

Hold the door open

It’s hard getting a show on television or a streaming platform. So when you get a show on the air and you’re opening up your writers’ room, you’re hiring your friends who are writers because you trust them, right? So how do you meet your writer friends? You meet them on other shows — but the Catch-22 is if a White writer has a show and it gets picked up, and most of the shows he or she writes on have White people, guess who they’re mostly going to hire? It kind of becomes this self-fulfilling prophecy. When we get a show, we have to open up the door to have more writers of color on, so when they get a show, they open more doors for writers of color.

Hire Black crew so we have people of color behind the cameras. In the production department and in the editing department, grips and gaffers. You have to make a concerted effort to get those people into those spots. You have to make a forceful effort to say, “When I do it, this is the way I’m going to do it, and I’m not discussing it.”