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?
Steve Hely on Twitter. The funniest person on the planet. Also, Trump Regrets on Twitter. It’s funny watching people who voted for Trump, tweet how fucked they are now. It’s hysterical.
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.
11. What book are you most likely to give as a gift?
I’m married with three kids, I have no time for books. Books can go fuck themselves. But, also probably, The Bible.
12. What’s the nicest thing anyone has ever done for you?
My wife does amazing things for me every day. And I’m not saying that to score that many points. But when she told me that she supported me being a writer 100% (when I was still a teacher) and there was no plan B, she inspired me in a way I can’t explain. I can never thank her enough for that. Ever.
13. South Park or Family Guy?
South Park. Hands down. They had a talking piece of shit as a character? And he was brilliant!
14. You have an entire day to do whatever you want. What would you do?
Honestly, lay in bed. Drink. Postmastes all the food that I shouldn’t be eating. I don’t need much with how much I work.
15. What movie can you not resist watching if it’s on?
Rudy. If anyone else says another movie, they’re lying.
16. The sports team or teams you’re most passionate about?
L.A. Dodgers. L.A. Lakers. Also, Green Bay Packers. Long story, but I rep Lambeau all day.
17. Where did you eat the best meal of your life?
The best meal of my life is honestly this greasy taco spot my dad would take me to after I’d work with him at his furniture store when I was a kid. It was called Bill’s Taco House by USC. The tacos were always insanely good, and we would just sit and talk. The best meal ever. Period.
18. The last movie you saw in a theater?
LEGO Batman with my kids. I only go to the movies now with my kids. It costs 100 dollars to take a family of five to the movies. Did you know that?! 100 dollars. Insane. I’m happy to break down a cost analysis for your readers on why Sour Patch Kids run $8.00.
19. Who was your first celebrity crush?
Janet Jackson on Differen’t Strokes. She dated Todd Bridges and I always asked why. Even I can pull Janet Jackson from Willis Drummond!
20. What would you cook if Nic Cage were coming to your house for dinner?
I’d buy a pig and first let us hunt it in my backyard with only our bare hands. Then we’d roast it over a fire while we drink red wine and smoke hella weed. I’d only ask questions about the filming of Raising Arizona. This sounds like an awesome night. Can Uproxx maybe set this up?
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