In Season 5 of the NBC series The Blacklist, Raymond Reddington (James Spader) is feeling surprisingly unencumbered, when it comes to rebuilding his criminal empire. With Elizabeth Keen (Megan Boone) by his side and the secret about their family connection now out in the open, his lust for life makes their search for Blacklisters more fun than ever, as the line between her role as an FBI agent and her criminal instincts blur.
During this 1-on-1 phone interview with Collider, executive producer Jon Bokenkamp talked about this new chapter for The Blacklist, the challenges of keeping things interesting, five seasons in, the fun of having an actor like James Spader at the show’s center, always looking ahead to the endgame, reaching the milestone of 100 episodes, why this new beginning is so freeing for Reddington, the bigger mystery of the suitcase of bones, Liz and Tom’s (Ryan Eggold) relationship, and the biggest challenges in pull off over 20 episodes of a one-hour drama, each season.
Collider: Season 5 feels like a new chapter for The Blacklist and the characters. What are you most excited about, with what your doing this season?
JON BOKENKAMP: I’m most excited to go on the ride with Red. You’re right, it is a new chapter, and it’s a new perspective and headspace for this character. In a world where most people would probably be devastated and want to curl up into the fetal position on the floor, by having their business wiped out, Reddington finds it incredibly refreshing and embraces the notion that he’s suddenly unemployed and has to rebuild from scratch. So, well said. It is a new chapter.
When you create one of the most interesting and fun to watch characters on television, with Raymond Reddington, are there challenges specific to keeping him fresh, so many seasons in?
BOKENKAMP: I think James [Spader] is a big part of that, in terms of keeping the character fresh. The stories are hard to tell. The cases are difficult to break. It’s hard to find the Blacklisters that we hope you wouldn’t find on every other show. One of the things we take great pride in is that our bad guys are the people the FBI doesn’t know about. That is challenging. But I have to say, writing the character and his voice is just really a blessing. It’s super fun. He’s a guy who’s constantly trying to surprise himself. He’s always trying to embrace new experiences, so there aren’t really limits with where he can go. We’re not worried about his reputation or what anyone thinks about him because Red isn’t worried about his reputation or what anyone thinks about him, and that’s incredibly liberating to write for.
When you have someone like James Spader at the center of your storytelling, do you just throw anything and everything at him because you know he can pull it off? Is there anything you’ve ever found that he can’t do?
BOKENKAMP: Not really. He’ll tell us, if he thinks something is too far or if something tells us too much about the character. One of the things he’s very good at is being very protective of the character and having him remain a bit of a mystery. One of my favorite things to do is to Google strange, far flown places and hear him try to figure out how to say them. I’ve never met anybody who can play a run-on sentence without that many commas and no periods, and it ends up playing great. I think everybody in the room has fun playing a little wish fulfillment. We’re doing it through the computer and Googling places and dreaming up stuff, but that character is actually going out and living those experiences. It’s fun to throw weird things his way, and he is always up for it and open to it.
Typically, when you pitch a show, you have to present a multi-year plan. Did you have a five-year plan, at the beginning of this show, and did the long-term plan look anything like how it’s playing out now?
BOKENKAMP: We did not pitch what the entire plan was to the network, but we have always had an endgame in mind. I come from writing features, and it’s hard to sit down and write a movie and just start on page one and go, “Well, we’ll see where we end.” It’s like a math problem. You have to know what you’re working toward. We have always had that bible in our heads, which makes it very difficult, at times, to write the show. In ways, it has also deviated. We’ve tried to surprise ourselves, as we go along. We learned a ton about the character, and all the characters, in terms of who they are, whether it’s trying to write toward the actors, or seeing things that work and don’t work. That’s what’s not like a movie, at all. You’re living with these people each week and you’re getting to know them a little more. So, we’re exploring it and finding it, as we go along, but we also have looked at the map, before we took this road trip, and have a very good idea of where we’re going. We have the same destination in mind.
Now that you’re five seasons into this show, are you thinking more specifically about when that endgame is?
BOKENKAMP: We’ve always talked about it. We don’t have plans for landing that just yet, but it’s always part of a constant conversation. James has been one of the first people to say, we don’t know how long we’ll be on. We’ll be on as long as we can, so we’re always trying to pace ourselves, in terms of how much mythology we’re unpacking and how quickly we’re getting to our endgame, and along the way, we find great distractions and side trips. For example, Mr. Kaplan was a character that we knew very little about, quite honestly, in the beginning. In starting to write for her, and getting to know Susan [Blommaert] and seeing where that story went and how close she was, ultimately, to Red, it was a lot of fun taking a little bit of a detour to get to know her better. There’s also Glen Carter, who’s somebody Red goes to at the DMV. Some of the people that pop into the show, it’s easy to get distracted and go on a little journey with some of these characters that we don’t know so well and explore that.
When you hit the milestone of 100 episodes, especially in this day and age, when there are so many shows on so many platforms and it’s so hard to get one on the air and to keep it going, what does that feel like and what does it mean to you that the show has lasted so long?
BOKENKAMP: This sounds like I’m making this up, but I really haven’t processed that. I really haven’t thought about it. We’re just so desperately trying to break Episode 96 and Episode 97. It’s one day at a time. But at the same time, it’s a huge deal. I had no idea that we would get here, let alone that we’d get to Episode 2, or that the show would even be shot. I wasn’t sure we would even get to make the pilot. It is a big milestone, and to me, it just speaks to what a great team we have, between the cast in New York and the production. I’m always dumbfounded when I see a script be able to come to life and see how much better production makes it, and how international and big it feels. It really is a movie, each week. The idea that we’re very close to 100 of them is just mind-boggling.
How are you approaching the 100th episode? Do you have special plans for it?
BOKENKAMP: We’re literally just sitting down to break that. We’re finishing Episode 10 of the season, and Episode 11 will be our 100th episode. We have big turns and big changes that are coming, that are going to be really great story turns. So, I’d be lying, if I told you that I knew exactly what it was gonna be yet, but we’re very aware of the fact that it’s our 100th episode and we hope to have some surprises up our sleeve.
Last season dealt with the dismantling of Reddington’s entire criminal enterprise. Who is he without his system and his allies? Is that freeing for him, or does that make him unsettled and nervous?
BOKENKAMP: If he is unsettled by it, he certainly isn’t going to share that. In our first episode, he finds himself stealing a car and driving. After that, he says that he feels alive. He says, “I should drive more. Dembe is always driving. Why don’t I drive more?” There’s this childlike wonderment of the world around him. He’s been existing in this bubble, protected by money, assets and allies, and all of a sudden, he’s stripped of all of that. I do think it’s incredibly liberating for him. Reddington would be somebody who would have a very difficult time looking at this in a negative way. He’s so unafraid and open to new experiences and the weird and the wild that this is the last thing he expected to happen, which is exactly why it’s the perfect thing to happen right now. I think he really embraces it, in his soul.
Is Reddington somebody who has any self-doubt, or is that a completely foreign concept to him?
BOKENKAMP: Oh, I’m sure he has plenty of self-doubt. Often, what’s very interesting to me is when we find those things that make him afraid, and we certainly have that this season. There’s a very big new storyline involving a suitcase and some human remains that has him terrified. I think it’s often very telling, when we see how he feels about those closest to him, whether it’s Elizabeth, her child, Mr. Kaplan, or any of the people in his inner circle. Those are often very telling stories about where he is, emotionally, and what he’s afraid of.
How big of a role will the suitcase of bones play, this season?
BOKENKAMP: Those human remains are almost a character of their own. It is something that becomes very important. It’s something that Reddington is not eager to have Elizabeth find out about. It’s going to present some real problems. That suitcase is significant.
It seems like something is always forcing Tom to keep a secret from Liz, which can’t be good for them.
BOKENKAMP: Right, but in this case, she realizes that this man is her father and she is closer to him than she probably ever has been. She trusts Reddington more and is more open to him. So, the idea that Tom should follow through with the instructions of handing the suitcase over to Liz, as Mr. Kaplan instructed, Mr. Kaplan didn’t know that the secret is out and Tom is a little bit worried that Reddington might manipulate the situation, as he often does, and he feels like he needs to solve this on his own. He’s often not the most transparent husband and it’s certainly caused some marital strife. I wouldn’t expect it to get any rosier, real soon, but there’s some great stories that we’re gonna be telling and it’s gonna be really fun to have Tom back.
What are the biggest challenges in writing more than 20 episodes of a drama for television, and specifically for this show? Does it feel like a well-oiled machine, or is it possible to ever feel that way?
BOKENKAMP: I wouldn’t want to jinx ourselves by saying that it’s well-oiled. It always feels like it’s almost impossible to pull off. The episodes are very big and they’re packed full of story. Honestly, I’m a guy who’s written things that I love dearly, but that have never seen the light of day. Now, I have the opportunity where we’re in this great place where we’re basically writing a new movie, every 10 or 14 days, and they’re being made at a really great level. Yes, it’s terrifying, and looking at that white board and figuring out what the next story is, is terrifying, but somehow everyone rallies and we’re able to put it together. It’s a blast to be able to do it.
The Blacklist airs on Wednesday nights on NBC.
