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Prentice Penny’s Guide to Los Angeles

The “Insecure” showrunner and “Upscale with Prentice Penny” host shares his tips on living the good life in L.A.

Until recently, L.A.’s Windsor Hills neighborhood, where writer and producer Prentice Penny grew up, was a well-manicured secret.  “The houses were built by the same architects that built Beverly Hills,” explains Penny. “The homes are huge, and it’s so central and close to everything, which is why I think more and more people are moving back.”  

Given his upbringing in this pocket of quasi-luxury, Penny’s newfound role as the host of “Upscale with Prentice Penny,” a show on truTV about unlocking a luxury-adjacent lifestyle through everyday life-hacks, seems all the more fitting. “It’s about [upgrading] these things that you’re already doing but making them even better,“ says Penny, whose qualifications go far beyond a taste for the finer things. An executive producer on HBO’s “Insecure”, Penny wanted to bring a perspective he saw was lacking to the lifestyle space. “I’m a big fan of Chef’s Table and Anthony Bourdain’s No Reservations,” says Penny. “[But] I wasn’t seeing people of color talk about these things. Like, my friends and I are doing these things and there isn’t anyone who looks like me, and who loves all these great things, but also loves hip-hop.”

Photo Credit: Justin Jackson/truTV

An aspirational show that’s all about inclusivity, “Upscale with Prentice Penny” doesn’t stop at challenging racial barriers. As seen on last night’s episode, the program also takes on toxic masculinity.  “We did a segment on men getting manicures,” says Penny. “At a spot on Melrose created by African American men called Hammer and Nails.” The verdict? “It was the first manicure I’d ever [had], and now I’m hooked!”

Besides his newfound self-care routine, Penny is an expert on unwinding in L.A. Read on for his full list of recommendations.  

Cup of Joe: Verve.  I’m not a fancy coffee drinker. I just need a punch when I wake up. Before I couldn’t tell the difference between good and bad coffee. I just thought it was all not great. But now I’m like, no, this is good coffee, and that’s bad coffee. So now I get it.

Power Lunch: Chateau Marmont. When you’re in this business, you’re constantly going on lunches. But the first time I went there, I was like, ‘Wow, this place is really cool. It just feels… something about walking into that spot and that hotel, it just feels like Old Hollywood and like you’re not playing around. 

Cocktail Hour: Seven Grand has whiskeys that you can only find off the beaten path. In the back they have a private bar called Bar Jackalope. It’s a bit more chill and low-key.

Retail Therapy: Wasteland. I’ve found Balmain pants there, and this Gucci luggage for, like, nothing. It’s like the kind my grandfather used to have from the 60s.

Field Trip: My dad would take me as a kid when we went to Olvera Street. We’d either get these fried taquitos from this spot on the corner which were amazing or we’d go to get these roast beef sandwiches from Philippe. I love the area, because you can walk, you’re by Union Station. I just love that whole area down there. That’s my spot. I love it. 

 Date Night: Crustacean is my wife’s favorite spot, so that’s my favorite spot. That’s where we go for our date nights. We have expensive date nights, apparently. You’ve got to get the crab. If you don’t get the garlic noodles and the crab, it’s like, what are you doing? 

Don’t Miss: Dodger Stadium. The experience of going to a Dodgers game is dope. It’s like the last affordable thing you can do. You can get a ticket for like eight bucks. Where else can you go see a professional sports game in LA for eight bucks? It costs more to park. But I’ve gone just for a walking tour to get a history of the stadium, outside of the games. I’ve done that a couple times because I’m a baseball nerd. 

Hidden Gem: Go to the rooftop at Hotel Erwin in the summertime. They have a great happy hour and you’re literally right there on the beach. You’re talking to your friends and watching the sun go down and it’s always chill.

Photo Credit: Justin Jackson/truTV