Master Class
How to Stay Black and Still Win in Hollywood, According to Director Prentice Penny
The ‘Insecure’ showrunner shares his keys to success
Update 6/7/22: Level has a new home. You can read this article and other new articles by visiting LEVELMAN.com.
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…
