He’s arguably most remembered for his time on Fox’s sketch comedy show MadTV and a series of commercials he made for 7-Up in the early 2000s, but Orlando Jones has been in the business a long time. His Hollywood career began in earnest when he landed a gig writing for popular sitcom A Different World on NBC, after which he penned scripts for other series like Roc, The Sinbad Show, and of course, MadTV.
While Jones has put together an impressive resume on the big screen as well — including varied roles in films like Evolution, Runaway Jury, Drumline, and a scene-stealing turn in Office Space — he returns to television this week with the premiere of Fox’s hotly anticipated fantasy drama Sleepy Hollow, in which he plays a Manhattan detective trying to make sense of a pair of grisly murders. In an inaugural interview for the Rotten Tomatoes TV Zone, we got to speak in depth with Orlando about the new show and why it’s more complex than it might first appear.
Rotten Tomatoes: If anyone hasn’t seen the trailer for Sleepy Hollow, can you give them a quick log line of what it is about?
Orlando Jones: So, the quick log line is, obviously, everyone knows Sleepy Hollow, and [Alex] Kurtzman and [Roberto] Orci — who obviously did Star Trek and Transformers and Xena and Hercules and the like — had a different idea, and the idea sort of goes like this:
There was a fight between good and evil happening during the Revolutionary War, and when we talk about how America was founded, we only talk about the Revolutionary War, but we don’t talk about the larger war that was going on. So, George Washington knew of this larger war, and he handed an order to a captain named Ichabod Crane, and Ichabod Crane wasn’t British, but he became a sympathizer and a spy on behalf of Americans on the British. He goes to kill this soldier, and he chops his head off, and then they mix bloodlines, and that guy turns out to be the Headless Horseman. The larger war is the war between good and evil, and he’s one of the Four Horsemen of the Apocalypse. 250 years later, the Headless Horseman wakes up and Ichabod Crane wakes up with him, and he has no idea why. He just thinks he killed a guy on the battlefield. And the battle of good and evil continues as we go through the history of this nation on a show called Sleepy Hollow.
RT: Wow. I usually I hate asking that question, but actually I’m really glad I had you explain that, because I like this whole “battle for good and evil” element to the story, and, plus, I never thought of the Horseman from Sleepy Hollow as one of the Horsemen of the Apocalypse. Holy crap.
OJ: And one of the cooler, cooler things about it is, the book of Revelations speaks of two witnesses. One of those witnesses is Ichabod Crane. The other witness is Abbie and her twin sister. Those two people get linked up in the present day, because she’s just a cop in Sleepy Hollow who works for the sheriff, who’s played by Clancy Brown — amazing — and Clancy Brown gets his head chopped off. The next thing you know, some other people die, and next thing you know, I’m sitting in my office in Manhattan, thinking I’m on to bigger and better things, and two people get killed in Sleepy Hollow, and I get sent down to try and deal with an investigation, wherein the word on the street is a headless horseman rode up and chopped two people’s heads off with a blade heated above 500 degrees, and I’m sorry, that’s not a reasonable explanation for anything if you’re a cop. That sounds like crazy, cuckoo talk. [laughs] Like, “Okay, tell the crackheads to go stand over there in the corner with the headless horseman story.”
RT: That’s a particularly bad day at the office for a cop. My god.
OJ: Yeah, and as you would imagine, if somebody killed two people that way, that would be a big story, and so it is a big story, and with that, Sleepy Hollow is under the microscope of modern times, while a guy is bringing a world into this world that I’ve never heard of and never seen and don’t believe in and don’t have any interest in really hearing about. I mean, two people have died and I need a real explanation. I can’t take this to my boss, I can’t explain this. It doesn’t make any sense. So, you know, we don’t ask people to believe it, because the show goes in with a healthy amount of cynicism. But the left turn in this whole thing is, it’s hilariously funny. I mean, you will laugh at multiple points throughout the story out loud at stuff. It’s sort of wild. It’s not a procedural, it’s not a serialized show. It’s just sort of a summer blockbuster, and you are in it, and it’s sort of happening every week. Honestly, that’s the best description of Sleepy Hollow if you haven’t seen the trailer.
RT: Man, I love it. Thank you. Well, when I watched the trailer and got to see one of the last moments, a couple cops bring up a really good point. They’re yelling things at the Horseman, and they’re like, “Wait, can he hear us?” I thought, “Man, I think I’m gonna like this show.”
OJ: It’s hysterical.
RT: And when Ichabod Crane shows up, he is so filthy — he’s been on the battlefield, after all, and there’s been time travel. I’m really hoping that the pilot includes an extended bathing scene.
OJ: [laughs] So basically, you’re saying, “I get it. It’s funny, and it’s action, but can I have some lady-porn, please? Bathe Tom Mison, please?”
RT: Yeah, exactly. Now, I know Fox is not known for their extended bathing scenes in their shows, but, you know. Let’s talk about Captain Irving some more. So, this is not the first time that you’ve played a man in charge, nor is it the first time you’ve played a man in charge when there’s supernatural things going on. Like in New Amsterdam, right? Is that a stretch?
OJ: Okay, New Amsterdam, wow. You’re good.
RT: I know. Listen, I went into the backlog for you, Orlando. You’re an honored guest.
OJ: Okay, I will take that. But, there’s a marked difference between these two. Wilcox is crazy. I mean, can barely keep it together, guy who walks down the street homeless in New York City and yells at you with that tone of voice that makes you cross to the other side of the street? Wilcox is that kind of crazy. Detective Irving is not.
RT: He’s just a dude trying to figure out where somebody’s getting a blade heated up to 500 degrees.
OJ: He’s a dude trying to look for real world answers to problems. You know, he’s a guy who, like we all… We hear things sometimes and people say “conspiracy theory.” And then we later start to discover that that conspiracy theory was true; that happens sometimes. But, you know, until that happens, some guy spends fifteen, twenty years going, “I’m telling you, the Earth is really not flat, yo. It’s ROUND.” [laughs] “Look at this crazy person who claims the world is round!” I mean, that day happened, you know? And then the next argument was over the circumference: “How round is it?” And Christopher Columbus, he was so wrong that he missed two continents.
RT: That’s true. I hope that Irving, as we watch him, misses some continents, that we get to fill in for him. This sounds like a very interactive show. Is the audience going to get stuff revealed to them? Are they omniscient? Do they know everything, or are they kind of discovering everything as the captain and Abbie do?
OJ: I don’t think it’s possible in the same way that you’re thinking, because the show’s path isn’t linear in that way. There’s such a mythology to all of this, and what I’m describing to you is really just one aspect of it. You kind of have to see it to really get it. Because, come on, you know how this works. Every year, all year long, we as actors and producers and writers and directors — whoever we are — come and say, “Hey man, but this one is really good. Hey man, but this one is different. Hey man, but this one is groundbreaking.” Right? And that’s become a log line now, so nobody really believes it, you know? At least I don’t. When I hear it, I go, “I?ll be the judge of that.” When I first saw the new Batman, the Christopher Nolan version, I was like, “Whoa! Okay, now that’s awesome. That’s totally different.” And I think Sleepy Hollow really is that, but people will make that determination on their own. But it’s hard to be interactive with it because you’re so immersed in it, and there’s so much going on. You could go back and watch it again, and get caught in a totally different strain. And that’s weird for network television. Or, you know, that’s just kind of weird in general.
RT: Is it kind of accurate to describe it as a cross between some American Horror Story elements with a Once Upon a Time flavor? Because this is based on a story that we’re all relatively familiar with.
OJ: If any of those shows were funny, yes. If any of those shows had not just supernatural, but mythology. You know, it’s not like the Headless Horseman is the only beast. The Headless Horseman is a tool. He’s the first Horseman of the Apocalypse; he’s not in control of anything. What woke him? How did he come back? So, there were witches fighting in the Revolutionary War back when this country was being founded, so that look is a supernatural look and a mythological look. You’re meeting creatures and things that have powers that you’ve never heard of before. So, yes supernatural, but yes mythology, but then funny, and then sort of action, but not following the same roads, because the road we’re on is the book of Revelations. So, more National Treasure meets Da Vinci Code, but like a summer blockbuster, but it’s in Sleepy Hollow, and it’s kind of incredible. It’s definitely a world unto itself.
And I think when I look at those shows, both of which I really like a lot, that’s what I imagined Sleepy Hollow would be. I thought it would be like those shows, because those shows are awesome and I’m a fan of them, so I was like, “Oh man, we’re going to do a show like that!” And then, you get in it, and you’re like, “Oh my god, no, this is actually so much bigger.”
RT: I’m into this. It sounds like Captain Irving has his work cut out for him, too. If there’s more monsters, I’m already glued to the set.
OJ: Let’s just say they show up with exacting specificity and regularity, and when you see the first episode, Headless is not the scariest thing in the first episode. Not even close. The scariest thing in the first episode is the thing that controls Headless. That thing is mortifying. That thing is what you have nightmares about. That’s what’s so cool about it, because that thing is the thing that Abbie has nightmares about. It’s so cool.
RT: So you guys film in North Carolina, right?
RT: So you’re basically running around terrifying the residents of Wilmington, North Carolina.
OJ: We’re doing that if we’re in the present day, but it depends on where we are. Sometimes we’re in the 1500s, sometimes we’re present day, sometimes we’re in the 1800s. It depends on where we are.
RT: You guys started shooting over the summer, right? Are you still shooting now?
OJ: No, we’re in production right now. I was on set at 2am this morning, East coast time.
RT: Man, that’s bonkers. And you’re so coherent. You’re a total pro.
OJ: It’s been fun, but yeah, it’s been crazy. I’ve been up for two days. I literally went to work at 9am, wrapped at 2am, got home at 3am, got on a plane at 5am. I got in a car at 5am, got to the plane at 6:30am, connected two hours in Atlanta, landed. An hour later, I was in makeup and wardrobe, and at 2:30, I started doing press, which I did straight through until 4:35 — 28 interviews — and then we did the screening in the Hollywood Cemetery last night. They showed Sleepy Hollow to 2000 people who came out to see it in the Hollywood Cemetery, which is like the coolest thing in the world, because it’s the Hollywood Cemetery, man! I remember seeing, like, Casablanca there; it’s awesome. So we did that, and then got home at midnight, did Access Hollywood this morning, and now I’m talking to you.
RT: Good lord. What a trooper. Hollywood is so glamorous, isn’t it?
OJ: This is the nasty underbelly! [laughs]
RT: So tell me more about the cemetery screening really quickly. What was the air of the cemetery like? Were people freaked out by it? Would you pop up behind somebody and scare the crap out of them?
OJ: You know, the cemetery’s sort of a different thing. It’s not sort of a gag-y thing there. It’s more like, you’re watching the Hollywood stars where they’re buried. For me, I never imagined in my wildest dreams that that would be done, because [Cinespia] shows the classic [movies] there. So to have Sleepy Hollow screened there in its inception is really kind of a crazy idea. I was a little taken aback the whole time. I was like, “Oh my god.” I was too nerded out, you know? My geek meter was high.
RT: I would have been nerded out, too. And terrified, a little bit. I don’t know if I could have handled a screening of Sleepy Hollow in the cemetery.
OJ: Yeah, that was just an extra fun layer, right? You know, you’re in a cemetery, and it’s kind of spooky, and it’s Sleepy Hollow. Honestly, I was surprised how many people came out. 2000 people?
RT: Listen, people love that cemetery, and they love Sleepy Hollow, and they love watching headless guys run around on the side of the mausoleum at Hollywood Forever. That is a good time. That’s a nice Sunday night.
OJ: Right? I mean, look, if you’re a nerd… I’m like, “Oh my god, I never thought I’d get here. This is the best! This is totally the best.” [laughs] This is having wine with Francis Ford Coppola, you know what I mean? This is somewhere in that territory. I’m hanging out with Francis Ford Coppola, and me and him are just chit-chatting. And I’ve done that. I mean, what a lovely guy, and what an incredible host.
RT: Okay, just to be honest, I don’t feel sorry for you being up for 48 hours straight now.