By Natalie Abrams
February 21, 2017 at 07:34 PM EST
Robert Falconer/The CW
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Oliver Queen has truly been through the wringer this season.

During the fifth season of Arrow, Oliver (Stephen Amell) initially took up trying to protect the city without his team, trained a ragtag quartet of vigilantes, one of which went on to betray him — all while trying to lead the city as mayor.

Ollie’s job was made more difficult by the rise of a mysterious new big bad, Prometheus, who viewers came to learn was the son of one of the men on Oliver’s famed list of corrupt Star City citizens he targeted in season 1. Oliver’s past was literally coming back to haunt him as the legacy he’s thus far created was tested, especially when Prometheus essentially tricked Oliver into killing Anti-Crime Unit detective, and Felicity’s (Emily Bett Rickards) new boyfriend, Billy Malone (Tyler Ritter).

As Prometheus plans his endgame, so does Arrow — at least in terms of the original five-year plan for the series. (Don’t worry, Arrow has already been renewed for season 6.) EW hit the set of the Vancouver-based series to get Amell’s take on Oliver’s current predicaments as the show builds toward its big season 5 finale:

ENTERTAINMENT WEEKLY: We know that Oliver is going to end up back on the island this year. What surprised you about how he gets there?
STEPHEN AMELL: How it ends, I think, is going to be surprising, which is odd because we pick up what happens right at the beginning of pilot. I actually don’t know a ton about what’s going to happen when he gets back to the island. I just know that one of the things that I’ve been pitching in terms of just a logistical thing is going to actually be something that we utilize.

Arrow’s been going pretty dark in these last couple episodes. Do you feel like the show’s going back to that season 1 feel?
Well, it has to. One of the biggest revelations that we have this year is Oliver learning something about the person that he was in season 1, and more importantly, the person that we’re seeing in the flashbacks. He’s unchained in Russia in terms of responsibilities, and it has gone really dark in the flashbacks, but to me, that doesn’t negate the growth that Oliver has experienced. Obviously [between] season 1 and season 2, there was a very profound difference. His ability to not kill Slade at the end of season 2 was important, and his ability to walk away at the end of season 3 was important, and his ability to not view the world completely in black and white at the end of season 4 and killing Damien Darhk again was important because it really showcased that it really is about protecting the people who are closest to him. That’s going to force him into morally questionable decisions; to always take the moral high ground is just not a luxury that he has.

During Wednesday’s episode, the police actually target the Green Arrow. What is Oliver facing both as Green Arrow, but also as mayor?
Well, it’s interesting what we have coming up. Oliver gets put into a situation where we’re effectively vilifying the Green Arrow with a lot of things that I’m not entirely sure that we can unpack, in terms of what people are accusing him of, what the mayor’s backing up and saying he did, because he doesn’t have a choice, and it’s a lot for Oliver to deal with as mayor. We actually get to focus on the task of governing Star City, and I’ve really been enjoying it. We’ve actually had multiple episodes where in one episode I’m simply not in the Arrow suit and then multiple episodes where I’m in it for a very, very short period of time, which is a departure for us. A lot of things that we’re doing this year feel like a departure for us, and I know that that has created certain elements of angst in the fan base. People like certain things, but you just have to do it. You have to constantly try new things as a television show.

In a season that’s taking a look at Oliver’s legacy, does he feel at fault for everything that’s happened because it all stems from his choices in the past?
That’s a trope that we lean on a lot in the show, but I actually don’t feel as though Oliver has done that. Obviously, he’s responsible for the death of Detective Malone, and we even reference in an upcoming episode that that’s something that he’s going to live with for the rest of his life, but I feel as though Oliver has really moved past the past where he might have been a little bit mopey.

I’ve actually been thinking a lot about the team in general and everybody — this is not to say that they haven’t gone through some aspects of tragedy, but Diggle was in a federal prison and is now at the very least seeming happier and on the path to redemption. We’re moving into a very interesting arc for Felicity and a purpose for her that exists outside the team, which I think is incredibly important. Curtis is in a better spot despite the fact that he’s having some marital issues. Rene was kind of a directionless individual until he found the team. Same goes for Dina in terms of she was someone who was on a murder spree and then became lost because she didn’t have a purpose anymore, and now she’s finding it on the team. Even Quentin seems to be on the road back a little bit. Obviously the main exception there is Thea, and I think that there’s a significant worry for the state of his sister, but in general, I feel like there is a bit of a sense of accomplishment. Again, it’s not without tragedy, because that’s the nature of our show.

RELATED: Arrow to delve into Oliver’s killer psychology
 
How will Oliver feel about Felicity returning to her hacktivist ways and forging her own path?
I like the way that we handled it. He knows that she’s into something, and he’s bothered right now — not that she might have a new venture, but by a certain response that she gives when Oliver catches John doing something [in the Russia episode]. That episode is a lot about me knowing that something is going on with both of their characters, and they’re just not telling me. Now, there is some resolution for John toward the end of that episode, but for Felicity’s character, it’s not something that she and Oliver discuss until they have what I think is actually quite an adult conversation about it. But he knows that she’s into something, and he knows that she doesn’t want to tell him about it, so he’s dealing with that in his own way.

Do you think Felicity and Oliver can ever get back to where they were in terms of a solid working relationship?
I mean, there was a distance in the early part of the year. And I never want to sail over something as traumatic and significant as the fact that Oliver was tricked into killing Detective Malone and everything that that’s putting Felicity through. I do think that there are a lot of unanswered questions in terms of how did they get from where they were at the end of season 4 to where we found them in season 5, and I am positive that we answer those questions.

Do you think they ever could be a couple again?
Sure. Of course. We know what came between them; it was a lack of trust. Felicity walked away, and Oliver let her. I mean, we live in a television world. Fences can always be mended.

Oliver also believes that Black Siren can be redeemed. Will we see more of that by season’s end?
I don’t know if we see it before the end of the season, but I do like that idea, and I do take that as a sign of growth that he’s looking for that little kernel [of redemption] that maybe exists somewhere.

What can you tease of what Talia al Ghul actually wants from Oliver? How does Oliver not make that connection when meeting Ra’s al Ghul and Nyssa al Ghul?
Well, pay very close attention to whether or not she ever says her last name. A) She never says her last name, and B) I understand that this can get slightly confusing, but Oliver has never met, at this point in the story, Ra’s, has never met Nyssa, knows nothing of the fact that Sara is alive, is unaware that Malcolm was part of the League — he doesn’t know any of these things. It’s as simple as Talia is her own woman who sought Oliver out because she thought he had the capacity to do good in the world. It is something that we address in the show coming up pretty soon.

With Prometheus teeing up his endgame, does Oliver worry that everyone around him either ends up dead or hurt?
That’s one of the interesting things. To me, one of the interesting things about Prometheus is how little he cares about the people that surround Oliver. They are all simply pawns to take him down, which obviously does inherently put them in danger, but I think that one of the things that Oliver’s done over the course of this year is just learned to trust people and learned to accept that when someone says, “I know the risks, I choose to be involved anyway,” that that’s their decision to make. I think Oliver worrying that everyone in his life that he touches somehow dies is hopefully something that he can get over, because that’s just the nature of the path that he chose.

RELATED: Arrow‘s Stephen Amell, EP Marc Guggenheim talk series ending

We know that the flashbacks are going to be over by the time we get to the end of the season. What does that mean for a sixth season? What do you hope to see, as the show is basically not beholden to anything moving forward?
I am open and excited about any possible idea, whether that’s a simple flash-forward narrative that we carry through the season, which I think we did to varying degrees of success in season 4. If that means that simply the flashbacks do not exist anymore and it allows us to expand the universe in terms of focusing more on other people’s backstories, not even necessarily flashbacks of people’s home life, just their life outside of the Arrow cave, I think that’s interesting. We can do that because, quite simply, we have more time, we have more pages, we have more chance for dialogue. I know they’re kicking around some ideas, but truthfully I have no earthly idea if there is any sort of element that we will be bringing into season 6 or if we just simply acknowledge that we pitched the show as a five-year origin story and we got to do it, which I think in and of itself is an accomplishment. There’s not a ton left on television from new shows from 2012. Just the fact that we made it that far is worth patting ourselves on the back for, ever so briefly.

Would you want to see a flash-forward to Oliver’s death? Whether it’s a flash-forward to a year from now, 10 years from now, whatever, is that something that would ever interest you?
Yeah. I think that the key to a story like that is that — look, Green Arrow was obviously pitched as a five-year origin story, but we’re breaking the flashback story as we go along. There’s always an overarching plan, but it generally has to go season to season. Like, I don’t think we knew at the beginning of the season that at the end of season 2, Oliver would end up in Hong Kong. We don’t necessarily know that stuff, and that’s just the nature of episodic television in 23 episodes a year. I think that the critical element, if we ever did something like a flash-forward, would be to make sure that we understood the precise beginning point and end point of that story and all the things that went into it, because I think that if we try to piecemeal it together, especially because it’s a flash-forward, that it just wouldn’t work. You know what I mean? We’d have to know the end game if we did something like that. I mean look, I’ve always had a very specific idea for how the series would end. It came to me at some point during season 1, and whether it’s through a flash-forward or whatever, I just hope that we end up getting to do that.

Arrow airs Wednesdays at 8 p.m. ET on The CW. Stay tuned for more scoop from Amell, including his take on a potential Dinah Drake-Oliver Queen romance.

Episode Recaps

Billionaire Oliver Queen — under the vigilante persona of Arrow — tries to right the wrongs of his family and fight the ills of society.
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