The Winchesters Boss Talks Finale's 'Emotional' Dean Story, Those Surprise Supernatural Cameos — Plus, Grade It!

The Winchesters Boss Talks Finale's 'Emotional' Dean Story, Those Surprise Supernatural Cameos — Plus, Grade It!
Mar 2023

Warning: The following contains spoilers for The Winchesters' finale. Proceed at your own risk!

While watching The Winchesters' (season?) finale, you might have asked yourself, "Am I actually watching Supernatural?" Because Tuesday's episode not only included multiple scenes with Dean Winchester himself, aka executive producer Jensen Ackles, but also unexpected appearances from hunter Bobby Singer (Jim Beaver) and Heaven's new God, Jack (Alexander Calvert).

Let's recap just how Mary and John's tweaked love story fits in with the Supernatural mythology: After learning that the Akrida queen was a hunter that turned on humankind before being banished to another world, Mary and the gang summon the mysterious stranger (aka Dean), using his journal, but all that appears is his beloved car, Baby, because he's already dead. Mary uses the Impala to drive the queen straight through a portal, then returns with Dean behind the wheel.

Dean identifies himself as a hunter (alias: James Hetfield) and explains that when he got to Heaven (in the Supernatural series finale), he took Baby for a drive through the multiverse in search of an Earth where his family had a shot at a happy ending. That's when he caught wind of the Akrida, one of Chuck's last creations to wipe out existence if he failed. With Sam still alive, Dean wasn't going to let the Akrida possibly make their way to his brother's Earth. So as he explained to Bobby in an earlier scene, he gave John the letter from Henry to nudge him in the right direction.

Jack shows up to warn Dean about interfering, but Dean argues that Sam deserves a good, long life, and if Jack wants to cast him out of Heaven, so be it. Of course, Jack gives him a pass and tells him to finish what he started. Dean gives John and Mary his journal, then warns Mary to watch out for a yellow-eyed demon, before handing her the Colt. Now that the Akrida are gone, John and Mary are free to choose their own destiny, which they do by leaving town together, and Dean believes that he may have finally found a version of his parents with a true chance at happiness.

Below, showrunner Robbie Thompson talks about Dean's "pretty heavy" story in the finale and what a potential Season 2 might look like for The Winchesters. (The show has yet to be renewed or cancelled; click here for Thompson's comments on its future.)

TVLINE | As promised, we now have answers: This is another world's John and Mary, and Dean is coming in from Heaven. So why was this the right way into this story for you?
When Jensen and Danneel [Ackles] first came to me and pitched me the idea, which was John and Mary's love story told from the perspective of them hunting together, we all knew, obviously, because they had lived it and I had written some of it and we all watched it, that didn't quite line up. But we all really loved that core premise, and we also really loved this idea of hearing this story through Dean's point of view. We've often talked about, on Supernatural, the ways in which the Winchester family, God bless them, [has] a lot of intergenerational trauma and issues and shenanigans. It started a conversation like, "OK, how does this work?" We started talking about that core issue.

I had no interest in upending anything, for lack of a better expression, past, present or future of Supernatural. We're only a few years away from, I'm going to call it, the For-Now Finale, because, hopefully, there will be more story own the road... Obviously, the idea of the multiverse was pretty one-stop shopping, in terms of that coming up pretty quickly. And then again, it was a question of, "Will this still be an emotional story for Dean?" And it felt like we had a really interesting opportunity to tell a story with Dean's character, even though he wouldn't be necessarily in every single episode... There were dozens of ways to make it work, but this one felt like the one that would feel the most emotional, without obviously upending anything, and it felt like a story that we could tell about Dean, about where he is at when we meet him in, technically, the pilot, but throughout the finale of our first season.

We had a couple of opportunities when we were looking at a timeline issue of where could we exist that would, again, not upend anything, and there was really kind of only two spots within that. There was the spot that takes place in between Episodes 19 and 20, when what happens to Dean happens to Dean... So there was an opportunity to tell stories there, but that just didn't work for me because we wouldn't have access to Sam in that way, in a way that we could easily explain or at least emotionally explain, and that just didn't feel like it was a story that certainly I wanted to tell and none of us did. And the other option was when he was, obviously, in Heaven, because we see him arrive there and he has the scene with Bobby, but then he goes for a drive. That was instantly very exciting to all of us in terms of a space for us to live in and tell our story.

The Winchesters Boss Talks Finale's 'Emotional' Dean Story, Those Surprise Supernatural Cameos — Plus, Grade It!
TVLINE | There is a lot of Dean in this episode, which I'm sure is going to please Supernatural fans a lot. What kind of conversations did you and Jensen have about Dean's presence in this episode and his mission? Did Jensen have any strong feelings about any of the details? Did he have any ideas for this particular episode that you can share?

With the finale, [it] was really kind of the same talking points that Jensen had from the beginning, and I don't want to speak on his behalf, but he was really very clear about he wanted to narrate, he wanted there to be a Dean story, but -- I'm paraphrasing here -- he didn't want it to seem like this was The Dean Show. This needed to be a story about Mary and John. At the same time, he recognizes there is a strong desire to see that handsome face again behind the wheel of that car.

So it was really a balancing act. When we were breaking the story in the room, I called him up and pitched it to him. I was very clear, "This is going to be two scenes, but the second scene is a meaty one. It's going to have, obviously, some exposition because we're going to reveal what you've been up to," but really, it was the emotional side of it. I was like, "This is going to get pretty heavy."

Danneel is someone who is a really wonderful barometer for like, "Are we making sure we're telling a story for both Supernatural fans and Winchesters fans?" It had to work for both of them, and we didn't want Dean to just sort of take over the episode. But we all knew that as soon as we showed him in that photograph at the end of Episode 8, that there would be a lot of interest in, "Oh my God, oh my God, oh my God. Is Dean going to come back?" In fact, I remember one of my first conversations with Drake [Rodger], we were just in New Orleans and hanging out... And then as we were kind of getting into the nuts and bolts of the show, he was like, "Hey, so like obviously Dean is in the pilot here at the end. Is there any chance that we'll have scenes with him?" He really was just a fan of the show who wanted to act alongside Jensen. And I knew that if we [got] picked up, this was where we're going to build to in this first season. I was like, "Buddy, if we get there, I got you covered. Don't worry about it."

[Jensen and I] got really granular on the [second] scene about who we were going to reference, who we weren't going to reference, different little callbacks to different moments in the series. He improvised some stuff on the day as well... He was like, "When Carlos asks this question, I want to say like, 'That's a good question, Carlos.' We had talked about this, and we never said it officially, but I referenced the name Carlos in an episode of Supernatural, and in my mind, it was always the same Carlos, just a different universe. It was kind of a way to acknowledge that a little bit in a way without him meddling any further in this universe.

TVLINE | Fans are probably anticipating Dean appearing because of all the hints you've laid into the season, but Jack and Bobby being in the finale was a pleasant surprise. Can you talk about bringing them into it and what made these characters the right ones to include?
I think all the writers probably had their own separate list of legacy characters that we wanted to bring back. For me, there was no order of like, "Oh, this is my No. 1 or whatever," but the first name I wrote down was Bobby Singer, and there was two reasons: Jim Beaver has been in every single season of Supernatural, whether or not Bobby was alive or dead. So I was like, "Well, he absolutely has to be in Winchesters." But I love that character, and Jim Beaver as an actor is just someone that I absolutely adore, and I had a blast. I had never met him in person, and so the night we were out there shooting, it was pure joy, just hanging out with him, talking about old movies... For me, Bobby was kind of a no-brainer and a great found-family figure in Sam and Dean Winchester's lives. And he was also the last person that Dean had seen in Heaven before he went on the drive, so it made sense that he would be the person to potentially follow and help out.

With Jack, we kind of desperately needed him to come in because we, literally, needed a little bit of a deus ex machine there at the end. Jack was a character that was created after I left [Supernatural], so I never got a chance to work with Alex, but I'm just a huge fan of his... We needed somebody who had that level of, frankly, like power and his gravitas to really step in there at the end and sort of right the ship.

The Winchesters Boss Talks Finale's 'Emotional' Dean Story, Those Surprise Supernatural Cameos — Plus, Grade It!

TVLINE | Season 1 had this very clear story trajectory with John and Mary meeting, the Akrida as the Big Bad, and then the mystery of how all this is happening within the Supernatural mythology, which you resolved. With this finale, there's a sense of closure to John and Mary's story. They go off together, there's that beautiful montage, which feels very much like, "We're wrapping this up." What do you see a potential Season 2 being about it if the show is renewed?
That's a great question, and I'm going to be judicious with my answer because I don't know what's going to happen, obviously, [at The CW]. I don't think anybody does at this point. These are interesting times, as the kids say. We looked at [our first season] as chapters, and this first 13 episodes, whether we were going to get only 13 or 22, we wanted to end this chapter, both on the emotional side with Dean and on the plot side with the Akrida. That was by design, and some of it is exactly what you just said, which was this was the big romance of the, for lack of a better word, meet-cute of it all, and to me, it was an ending [to] that part of the story.

In terms of where we can go, the scale of this was, "It's the end of the world," and all of the normal hijinks. But that also kind of matches the scale of what you feel when you're in that young romance, where you're like, "Oh, my God, it's us versus the world." In success in a Season 2, without spoiling anything, we certainly know where we would want to go, and I think maybe you and I even talked about this as well when we spoke earlier [this season], the romance of this was always what was most appealing to me as a writer because I'd never really written much of that stuff in my career. The first act of that is always the meeting and the falling in love and the intensity of that. But then it's a question of how do you sustain it, and what does that look like, especially in a universe where monsters are real? And so we have an incredible opportunity, given a chance to tell more story, to really get into the meat of what it means to be in a relationship in this kind of context, what it means to sustain love, not just fall in love.

It's one of the reasons why we ended it the way we did. We didn't really change anything when we found out we were only going to be 13 episodes. We wanted it to feel like this chapter had closed and that the plot mechanics had closed, but that, emotionally, there was room for more story. There's so much more story to tell about where these two kids go. And because now, as Dean says at the end of the episode, they have a chance to write their own story that doesn't have to be necessarily what happened on our version of Supernatural, we have an opportunity to really go into some interesting places. I'm hopeful that we get a chance to do that.

The Winchesters/Supernatural fans, what did you think of the finale? Grade it below, then hit the comments!