“Insecure” Showrunner Prentice Penny Talks “Upscale” & Teases Season 2: It’s going to be some men in Issa’s life.

"Insecure" Showrunner Prentice Penny Talks "Upscale" & Teases Season 2: It's going to be some men in Issa's life.


“Insecure” Showrunner Prentice Penny On “Upscale” & Teases Season 2

While you may not know who him by name, you certainly know the creative genius of his vision on the hit HBO series, Insecure, starring the hilariously real, Issa Rae. Prentice Penny has worked as a writer and producer on various network shows including Girlfriends, Scrubs, Happy Endings and Brooklyn Nine-Nine. In his interview with Rocsi Diaz and Nina Parker on their weekly podcast, The Little Black Dress, Penny gives us a front seat of what it’s like to be the show-runner on the hit HBO series and his new TruTV show Upscale With Prentice Penny. Peep the excerpts below.

"Insecure" Showrunner Prentice Penny Talks "Upscale" & Teases Season 2: It's going to be some men in Issa's life.

Bottom: Lisa Joyce, Yvonne Orji, Issa Rae, Jay Ellis. Top: Natasha Rothwell, executive producer Melina Mastoukas, showrunner Prentice Penny

On why it is important to create a family atmosphere for Insecure’s cast: 

My first show I was on was Girlfriends back in the day and Mara [Brock Akil] who basically taught me mostly everything I know, just always created that feeling. So, I said whenever I get a show to run, I wanted to do the same and that was important. We try to do that with Insecure.

"Insecure" Showrunner Prentice Penny Talks "Upscale" & Teases Season 2: It's going to be some men in Issa's life.

Insecure writers dressed #Upscale in honor of  ‘Upscale With Prentice’.

Part of the reason why I wanted to come and run the show, I felt like at that point I had been working with network television for 12 years. And I was like, when will I ever get a chance to do this show again? How much longer will I have to wait on Insecure, if I don’t try to leap at this right now to get this job, I have to wait another 15 years.

"Insecure" Showrunner Prentice Penny Talks "Upscale" & Teases Season 2: It's going to be some men in Issa's life.

On creating the vision for “Upscale with Prentice Penny”:


It was kind of two fold. It never started from a place of wanting to be in front of the camera. It was like, we love BBQ, and we love Bourbon and Whiskey. We should fly to Kansas City, rent an RV, drive for two weeks and tour urban and BBQ places for fun. The show is more objective. It’s not about my actual taste.

"Insecure" Showrunner Prentice Penny Talks "Upscale" & Teases Season 2: It's going to be some men in Issa's life.

Prentice Penny

It’s actually about me exploring these worlds. You explore them too and see what works for you in them. That’s literally like the whole show. Growing up you learn one thing and then you get older and you start asking questions. We did a segment about wine. And I was like, ‘Look, this is a common thing’. I walk into a wine store and try to figure out if this is a $10.00 friend or a $20.00 friend. The show is there to make you feel free to ask questions.

On season two of Insecure:

It’s going to be all the characters you love and more people. Issa got broken up with so it’s going to be some men in her life.

Click here to listen to the podcast. 

Check out the ‘Upscale’ teaser below.

A post shared by Prentice Penny (@the_a_prentice) on

By @TheFeministaChronicles


Authored by: TJB Writer