Like so many people, Christopher Jackson has really stretched himself in the last year, particularly as a parent. “We’ve been helping our children with their classwork and trying to be productive in our own jobs and careers,” he says. “I am a lot of things, but a math teacher, I am not.” Indeed, he is an Emmy- and Grammy-winning actor, singer, and musician who has starred in the original casts of some of the biggest Broadway shows of the last quarter century. This month, he appears in the adaptation of one of them: In the Heights, which hits theaters and HBO Max on June 11.
Jackson chatted with Conde Nast Traveler about taking trips to reconnect with his wife, the pleasures of a great airport lounge, and why he thinks New York City is actually underrated: “I’ve been here for two decades, and there’s still so much of the city that I haven’t really touched,” he says.
The first destination on his post-pandemic wish list:
Punta Cana. It is a sweet spot for my wife and I. When you have about eight days to dip out of a Broadway show and find some sand, that’s been our go-to. We’ve had some wonderful experiences there, and I cannot wait to go back. We’ve tried several resorts throughout the years. Just prior to the pandemic, we joined the Unlimited Vacation Club, and so [have been to] some of the Dreams Resorts, and Zoetry is a particular favorite of ours. That’s going to be our first trip, for sure.
His typical approach to leisure travel:
I tell my wife this all the time—at some point, I’m going to become adventuresome on vacation. But most oftentimes, all I want to do is play golf and drink rum punch. I always say, I’m going to read three books while I’m gone. I read maybe 10 pages. My in-laws are here in New York, and so we’ve always had the benefit of having them [as babysitters] when she and I just need to go and reconnect with one another. Our lives pull us in such crazy directions, so it’s great to be able to use that time to just revitalize our relationship. We have an amazing friendship and those trips always just go so far to quiet the noise and allow us to get our own space for a little while.
His most important hotel amenity:
Great shower water pressure. I want to be in a shower that I could literally drown in standing up. Because I have such crappy water pressure in our house right now, that’s one of the things that I look forward to. I love a shower that’s just a deluge. That’s the best thing in the world to me.
On his fondness for a good airport lounge:
I have a real appreciation for the JetBlue lounge and the Delta lounge, so I’ve been known to show up three hours before a flight, just so that I can, especially before a business trip, get into that lounge and have a glass of wine or a cup of coffee or whatever the mood dictates. To organize my thoughts and my agenda in one of those lounges is super helpful. The Virgin Lounge at JFK is also spectacular. When my business partner and I flew to London several years ago, we showed up almost four hours before our flight, because he was coming from Newark and I was coming from Westchester county. We had a business meeting [there] that kicked the whole trip off in such a productive way, because we were able to just grab a little table, have some dinner, and then really focus and enjoy the experience and get some things done.
How he spends his in-flight time:
It’s almost impossible for me to stay awake on planes. I don’t know if it’s just the white noise, but I’m not very productive on a plane, hard as I’ve tried in the past. I may be able to get a movie in, if it’s a long flight, but generally if I’m flying to L.A., I’m going to sleep most of that trip. I wish it weren’t the case!
His favorite theaters around the world:
I love the Pantages in L.A. The Orpheum Theatre in Minneapolis is also really special to me. That was the first out-of-town theater that I performed in for Broadway productions, where we set Lion King. We were there for about 13 weeks for that run, and that was great. I have seen some shows at the Guthrie in Minneapolis throughout the years, which is just a wonderful theater. I love the Steppenwolf in Chicago, another great house, and they always have such an amazing group of actors there. [My hip-hop group] Freestyle Love Supreme has performed in several comedy shows around the world. We were in Edinburgh, and when the festival’s going on, every available space turns into a theater, which I think is also just amazing. We performed in the state rooms there. I believe that they’re municipal rooms, but during the festival, they’re theaters, so they pack seats in, throw in some risers and all of a sudden, we’ve got a stage and there you go.
What makes for a special theater, as a performer or audience member:
Obviously, the piece that you’re doing has a huge influence on what works and what doesn’t. My favorite theater in the entire world is the Richard Rodgers. I’ve spent more time in that theater than I have in any other Broadway house. I know every corner of that, because I’ve spent years of my life and some of the best years of my career, with the best people that I’ve ever worked with, doing In the Heights and then coming back to do Hamilton. It’s large, but there’s not a bad seat in the house. The furthest-most seat, you can still make out pretty much who’s sitting out there during the performance. It’s very rewarding, because you know that the people that you’re trying to tell a story for are so close to you that they’re going to notice. They’re going to notice the beads of sweat coming off your brow. When they respond, you can literally feel it. Being on stage, there’s a nuance to—your performance is affected in the way that the audience is dancing with you, is engaging with you. And to my experience, that theater is like no other.
His go-to restaurant in New York:
My favorite restaurant in the city is Crown Shy, down at 70 Pine [Street]. My good friend James Kent is the chef there, and I was with him when he was drawing plans out on a napkin and showing what his vision for the place was. To see it come to fruition and then to see them manage it and weather this whole pandemic—and then come back slowly and the way that they care for their team there—is really spectacular. And it’s the best food that I’ve ever eaten.
The destination he wants more people to see:
I’m not saying New York. I’m going to say New York. I am not trying to be safe! I got to speak about what I know! The beautiful part about what has happened in New York over the past 10 or 15 years is that there are neighborhoods that have completely reinvented themselves. I’ve been here since 1993, and anytime I go into Williamsburg and find a little hole-in-the-wall restaurant, or anytime I’m out in Astoria, a neighborhood that I used to live in, it’s completely different. You can’t walk more than five feet without hitting a new restaurant and be like, “Oh, wow.” I ate at this restaurant called Shady Lady in Astoria. So good! It has these amazing cocktails, really creative. Somebody on set, one of our ADs, told me about it and I just happened to be rolling by and stopped into it. When people are coming here, I always say Times Square is like an amusement park, but there’s only three or four rides. Once you’ve seen it, taking all the pictures to prove that you were there, the rest of the city is just completely open to enjoy.
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