Prentice Penny is the showrunner for the HBO comedy, Insecure and previously served as a writer and executive producer on Fox’s Brooklyn Nine-Nine and ABC’s Happy Endings. He’s also the host of the new truTV series, Upscale with Prentice Penny, which the network bills as a show in which Penny “combines his passion for style and unique experiences with his comedic sensibility to give viewers attainable ways they can upscale their own lives.” (You can watch a trailer for the show here.) Penny was nice enough to take a few minutes to answer our 20 questions questionnaire recently.
1. You walk into a bar. What do you order from the bartender?
Templeton Rye old fashioned. Or Rittenhouse Rye old fashioned. But I whisper, so it seems cooler.
2. Who’s your favorite person to follow on Twitter and/or Instagram?
3. What’s currently waiting for you on your DVR or in your streaming queue?
Queen Sugar. I tell people I’ve seen it, but I haven’t. I’m not proud of it, but I don’t want to be left out of the social discussion.
4. It’s your last meal — what are you going out with?
Seafood tower and a ribeye from Mastro’s in Beverly Hills. Done.
5. What websites do you visit on a regular basis?
I go to three every morning and it pretty much sums me up. CNN, ESPN, Worldstar. Not always in that order.
6. What’s the most frequently played song on your mobile device?
Right now? I’m deep into Migos and Gucci Mane. But I have different moods for different days. Last month, I was on a Metallica kick. Master of Puppets was banging all through my Inglewood neighborhood. I got stares.
7. If you could go back and give your 18-year-old self one piece of advice what would it be?
Don’t be so pressed to have sex. You’re gonna get more of it over the next 60 years, man. Calm down.
8. What’s the last thing you Googled?
Property Brothers Fan Fiction. Don’t make me explain.
9. Dogs or cats?
Dogs all day, son! Who’d pick cats? Why do cats even exist? They literally are the animal embodiment of Chris Elliott in Get A Life. That being said, I’m open.
10. Best concert of your life was…?
As a kid I saw Kid N’ Play with MC Hammer and that was the best show I’ve ever been to. Nothing even comes close. I was 15 years old, with my three best friends and no parents…. There were also some people smoking weed in our section, and it was my first contact high. I ate hella nachos with my friends afterwards. It. Was. The. Best.