A Chat With Gil McKinney – ‘The Winchesters’, Cons and The SPNFamily!

As we wait to find out whether the Supernatural universe’s ‘The Winchesters’ will return for a second season, I talked to one of the show’s guest stars for its first season – Gil McKinney, reprising his role as Henry Winchester, patriarch of the Winchester family. One of the exciting things about ‘The Winchesters’ was having some of the cast of the ‘Mothership’, aka Supernatural, make an appearance – including Gil. He has also been doing the convention circuit again recently, so it’s been wonderful to see him in person as well as onscreen.

Lynn: How did you find out that you’d be playing Henry Winchester again? I’m assuming you didn’t have to audition for the part!

Gil as Henry with Jared and Jensen as Sam and Dean

Gil: It’s kind of funny, I remember exactly where I was when I caught wind of it. I was driving around running errands and got a text from Alaina Huffman, who played Abbadon on Supernatural. She left LA years ago, but she reached out to me and said hey, are you doing The Winchesters pilot, because your name is in the script?! I said, wow that’s pretty cool. No one had reached out to me yet, but I knew the pilot was in the process of being cast. She had been sent the script, and I don’t think she would mind me telling the story that she had an audition for Josie.

[Who we didn’t end up seeing on the series – at least not yet.]

Gil: I asked her to send me the script – not the whole script, but the audition material.

Lynn: The sides.

Gil: The sides, exactly. It was the scene in the pilot where they’re reading the letter from Henry, and it says Henry Winchester played by Gil McKinney in the sides, and I was like, that’s cool! That’s never happened to me before, but also kind of strange because no one had mentioned anything yet. That casting office knows me fairly well, I would say they’ve cast me in more shows than any other office. They’re wonderful. They’re called UDK, Ulrich Dawson and Kritzer, and they’re fantastic, some of the kindest casting people you’ll ever meet.

Lynn: They cast Supernatural too, right? I’ve heard many of the actors talk about how great Robert Ulrich is, and how great that agency is. I keep saying someday I need to buy them a fruit basket. A GIANT one!

Gil: So I called my manager, just to let him know, and then weeks, if not a couple of months, went by and I remember exactly where I was – in my garage putting together a motorized tractor trailer situation for my son – and I get a text out of nowhere from Jensen. We’re very friendly but we don’t communicate regularly or anything, but I got a text from him out of the blue saying hey, do you have a minute to chat? I was like, yes Jensen, I’ve got a minute for you! So we chat and he tells me they want me to come play Henry on the show again, and I was just floored, I was so happy.

Lynn: I can imagine!

Gil: You know, I can only speak for myself, but as actors, the disappointments pile up so the victories become extra special, and that was just really cool. We had a really nice conversation – he was on a boat somewhere in the swamps of Louisiana. I want to say he was with Robbie Thompson and they were looking at alligators or something cool like that. I was like, that sounds nice man, I’m putting together a motorized tractor for my one year old. I said, this is the best call I’ve gotten in a long time and of course, anything you need.

Lynn: That’s awesome.

Gil: I’m over the moon because, you know, conventions and Supernatural are one of the best things that have ever happened to me, but I did one episode in Season 8 and one in Season 9 and they never got back to Henry. I’ve been lucky enough to travel all over the world doing conventions and the one question I got more than any other is when is Henry coming back, are we going to see Henry again?

Gil answers questions at a Creation Supernatural convention

Lynn: I think we all thought we would. He’s part of the core family, the Winchesters, so I really thought we would.

Gil: Well, you know, I’m not in the writers room, I don’t know why decisions are made one way or the other. All I do know is I spoke with Adam Glass somewhere during the course of those years – Adam basically created and wrote the Henry Winchester character and introduced it and cast me, which I’m forever grateful to him for. He also flew me back to LA to do an episode of Criminal Minds Beyond Borders that he was writing on, he offered me a guest star on that. One day we were sitting in my trailer at CBS studios and talking about everything and he expressed to me that he fought and fought to have Henry come back in a much bigger way, but for some reason, in the writers room not everybody was on the same page. They wanted to go in a different direction. One producer just felt like Henry should stay dead, which is hard to hear. So I didn’t lose hope but as season 14 and 15 came, I just had to kind of accept that Henry likely was not going to be back on Supernatural. And that was a tough pill to swallow.

Lynn: I’m sure it was. It was a great character, and I think a lot of people wanted to see more of Henry.

Gil: I’ve done a lot of guest stars on shows, and hands down that role is my favorite, because it’s such a cool show and such a great character. Especially in that first episode I did, As Time Goes By, when Henry is in almost every scene. So as an actor, I spent a couple of weeks in Vancouver, on set pretty much every day. It was so much fun to shoot!

Gil with Serge Ladouceur on the set of Supernatural

Lynn: And it was such a great episode.

Gil: So fast forward to this call from Jensen and I was like, wow, it’s finally happening – Henry is gonna get to come back finally, after all these years!

Lynn: You never know, do you? I mean, what’s interesting is that As Time Goes By is a fan favorite episode. So it’s interesting that they didn’t want to revisit that character, because obviously, by your popularity at conventions and the popularity of that episode, the fandom thought that it was a character they would have liked revisiting. But clearly Jensen also never forgot that was a great character, too.

Gil: I think you’re exactly right, and you know I’m not saying that the writers and producers don’t listen to the fans, but not always, because that’s always been the sense that I got, which was part of my frustration. Like I would get all this positive feedback about Henry and that episode, and I’m just like, the fans seem to love it, so why aren’t they doing more? And then as an actor you start to take it personally, of course. I’m sure at some point I’d spoken to Jensen and Jared along the way about it. They were creatively involved for sure, but not to the level of those decisions. But yeah, it meant a lot to me that Jensen didn’t forget – and then you have a show called “The Winchesters”…

Lynn: Which seems like a no brainer for Henry Winchester.

Gil: It was about how they [John and Mary] meet so it’s like, of course Henry’s got to be there. When I finally got the pilot script and read it, I saw that Henry was mentioned like ten or fifteen times.

Lynn: Much like finding John was the driving force in early Supernatural, finding Henry was the driving force for John to kick off ‘The Winchesters’. Did you know that ‘The Winchesters’ was actually taking place in an alternate universe? So it wasn’t our John and Mary, and presumably it wasn’t our Henry either. Did you know that when you were filming, or did you just play the same Henry that you played on Supernatural?

Gil: I didn’t know that, and with two small kids I haven’t finished watching the whole season yet, but I fully intend to find the time to sit down and really dive in. I heard it finished very strong. I guess in that last episode a lot of that was revealed, but you know, as an actor, we’re working on the show now, so I didn’t really know too much about that, and so I played it as the same Henry.

Gil as Henry on ‘The Winchesters’

Lynn: I’m sort of glad that you did. I wanted it to be an AU all along, because that way you don’t have to worry about whether it messes with canon, so I’m glad it was. Then I could enjoy the familiar faces from Supernatural, like Henry and you. One of the most emotional moments of the whole season was that interaction between Henry and John, and it’s partly because I did feel like you were the Henry that I knew more or less. What was shooting that scene with Drake Rodger like?

Gil: Filming that was so cool. I met them when I got to set the first day. I got fitted for the suit again, which was really cool, and then I went to set and I got out of the transpo van and the first people I see as I step off the van are Drake and Meg, John and Mary. They were the first people I met when I got to set.

Lynn: A nice welcome – they are both so very nice.

Gil: I had looked Drake up and thought man, he looks perfect, but to see him in person – it honestly reminded me of the first day I met Jared. The height, and he’s like Jared reincarnated, and he’s got a bit of Jensen in him too. He’s definitely a Winchester! I talked to Robbie about him, and he was like, when we met him we were all like, please let him be able to act, because he’s the guy!

Lynn: Luckily he can.

Gil: I gotta be honest with you. This was years in the making, so I usually have like kind of first day jitters on a set, like a lot of actors talk about first day jitters when you’re a guest on a show until you kind of get your bearings and meet everyone. It’s a lot, you know. And so I definitely was feeling a bit of that, but also just, you know, like the years of doing this, and being a part of this universe, and just wanting to deliver and to get it right. So anyway, I would say I felt a bit nervous.

Lynn: Of course, I don’t blame you.

Gil: I found out after the fact from Richard Speight, Jr., who directed the episode, we went to lunch and he told me that they were so nervous to meet me!

Lynn: Well of course, you’re Henry Winchester!

Gil: Yeah, it’s very sweet, you know. But I didn’t sense that they were nervous. Well, in hindsight, maybe a little bit. But you know they’re like 22 or 23 years old, something like that, and they’ve landed these amazing roles in this, potentially something that’s gonna be life changing for them, no matter what happens. But they were so gracious and so sweet. And I mean the whole cast really was awesome.

Lynn: Everyone I’ve met has been incredibly sweet.

Gil: So shooting that scene with Drake, yeah, it felt emotional. I just met him a few hours before shooting, but I knew who John was, and I had an idea of how I wanted the scene to go. But as an actor, you should just try to let all that go and let it play, right? And I’ll tell you, he was awesome. I don’t even know how to describe it but like he’s really really talented. They both are. The whole cast is super talented, but that kid’s a star.

Drake and Gil as John and Henry on The Winchesters

Lynn: With the two of you together, the emotion was really strong. Do you think it’s partly because in real life you are the dad of a son?

Gil: You hit the nail on the head, I definitely try to use that for sure. Some of those moments, I can promise you, I was thinking about my so. I don’t really know Drake, but I know what it’s like to have a son. And I just felt like Drake was very prepared, and he was a generous actor, really easy to work with. And I also felt like he really wanted to get it right.

Lynn: I’m sure he felt some pressure to do that – he’s actually a bona fide Supernatural fan. I had a long talk with him at New York Comic Con. I did the press room, and it was the first time I had met him, and we just got talking about Supernatural because he is a huge fan. He saw your episodes, so he knew how important Henry was. And I think that makes him even better in the role of John. He gets it.

Meg Donnelly and Drake Rodger at our chat at New York Comic Con

Gil: Oh, absolutely. Yeah, we had a funny moment where he had a line about the music box and he was struggling with the line, or he wasn’t sure how he wanted to say it, and I was like, listen. I pulled him aside and I pulled up that first scene in As Time Goes By, where Henry’s tucking John into bed, and he turns the music box on. I was like, do you remember this? That’s what this is like. And I was able to help him with that. But yeah, he gets the world, and he’s a really solid guy.

Lynn: And Supernatural alum Richard Speight, Jr. directed, right?

Gil: He did.

Lynn: It was a real Supernatural reunion!

Gil: Originally I went in to do the voice over for the pilot and I met some of the team, I believe John Showalter, their producer. I think Richard was originally set to direct Episode 7 and then somewhere along the way they shuffled the directors around. I let Richard know that I was gonna go down to New Orleans to work on the show, and I knew that he was going to direct an episode or two. I’m not sure how many he did, but we had this back and forth, and then he texted me out of the blue one evening to say I’m going to be there, I’m actually directing the episode now, so that was really cool to hear. Because to be honest with you, out of all the actors at the conventions – I mean, top to bottom, we really all care about each other and root for each other. Actors aren’t always like that, but I feel like we’re all genuinely close, but out of everyone I really admire Richard and look up to him so much. He’s just a little bit older than me, but I just admire his work ethic, and he’s a fantastic actor and a father of three boys. He’s been doing this a long time and I’m so excited and happy for him that all his hard work has paid off with this directing thing. I don’t think I could think of a better person to work with as a director. I got to work with him a little bit of Kings of Con too, which was obviously very different.

Richard Speight, Jr. directing The Winchesters (KSite TV)

Lynn: Oh, that’s right. I’m so thrilled for Richard too that he’s directing. In the early days of the conventions, he and I used to get together for a drink on Sunday nights after the cons were over, and do a wrap up of what went well and what didn’t etc. He told me early on that he wanted to direct, and I’m so happy that happened for him.

Gil: He’s just one of the smartest, funniest people I know, and I really look up to him. So when I found out he was directing it, it felt really cool, you know? He and I have a good relationship and a good dialogue and banter, and we don’t take ourselves too seriously, but we know when to [be serious]. That’s kind of how it felt on set. And actors like working with directors that are actors, because they kinda know how to talk to you, and they know what it’s like. Some directors are more technically savvy, good with the lighting and the movements, they know what they want, but when it comes to talking to the actors they sometimes don’t quite know what to say, and that can be frustrating for an actor. But a guy like Richard, he’s just perfect because he just he just hits it on the head every time.

Lynn: He directed some episodes of Jared’s new show Walker too, and every time I see something he’s directed, I feel a little bit like a proud mom. Or… big sister.

Gil: He told me he was lucky enough to be accepted into the Warner Brothers directing program, which I’m not sure it even still exists, but he was in one of the last classes that got to do that. From that and his relationships with the Supernatural world,  that kicked it off. And his relationship with Jared and Jensen – everybody loves Richard.

Lynn: I think the Supernatural cast has gotten to know each other in a way that most casts don’t, from doing so many conventions and traveling the world together, that bonds you.

Gil: It’s very cool. Sometimes people don’t really appreciate it or fit in, but they don’t stick around. Most of us go into these shows with a good attitude, and we do have so much love for each other. Of course there are little issues here and there, like brothers and sisters would have, of course people are going to butt heads, but at the end of the day I know I would do anything for any of those people. It’s such a blessing.

Lynn: For my last question, let me switch gears a little bit, because you’re also speaking of conventions. You’re very much back on the Convention circuit, and you’ve been doing some singing again, and I was thinking back to the chapter that you wrote a few years ago for the Supernatural book of cast and fan essays, Family Don’t End With Blood, about the encouragement of the Supernatural fandom, and how that got you singing again. So how does it feel to be back? How does it feel to be on stage singing again?

Gil wrote a personal and powerful chapter in Family Don’t End With Blood

Gil: It feels great! There had been a steady decline in the amount of conventions I was being invited to, the pandemic didn’t help obviously, and I felt like maybe it was coming to an end. Had it not been for ‘The Winchesters’ and getting to play Henry again, it very well could have come to an end. But I had always said to Creation, I’m here. If there’s a last minute cancellation, chances are I can probably hop on a flight at a moment’s notice, like I thank you so much for all you’ve done for me, and I’ll be waiting if you need me. And then at the end of last year I get an email out of the blue saying, do you want to do every show next year? I was like, wow, so does that include Hawaii??

Lynn: Right!?

Gil: It feels great to be back up there with Louden Swain, some of my favorite people. The feeling you get, just the energy, is amazing. It’s a total different beast than being on stage with say, you know, a wonderful pianist behind you. So yeah, it’s kind of sparked that for me again. I’ve just been grinding away with the acting thing and the parenting thing. I still hope that I can find the time and inspiration to try to write some original stuff again.

Lynn: Yes, I was going to ask if you were gonna do more original songs? I love the song you wrote for your dad, it’s one of my favorites. Any chance you’ll sing some of your original songs at conventions?

Gil sings one of his original songs at a Supernatural convention

Gil: Not at the next con. But yeah, there’s always a chance. I feel like I need to write something without suffering a tremendous loss. It’s in me somewhere. It’s just finding the time and the confidence in the end, and I need to push. Jason Manns is always in my corner if I want to collaborate with him, and I have access to so many amazing musicians. I think it’d be good for me.

Lynn: I would love that!

Gil: Because, you know, I’m not giving up on the acting thing at all, but it has been really tough out there for pretty much everybody I talk to, it’s a hard time for actors. I can’t tell you how many self tapes I’ve done, and if you really think about it you can think oh this is not going well. But you just do it, and I’ve gotten to a place now where I record on my Kindle, then I’ll record the other lines and rehearse with those other lines. The trick is allowing enough space in between those other lines to get your line in and not feel rushed! And I’ll just play the scene out basically with myself, you know, invisible person off camera, and I’ve gotten better at it. And actually I booked something a few weeks ago, so that’s all good.

[Gil guest starred in a CSI episode a few weeks ago, on which he played a character who kept you guessing for most of the episode – well done, Gil!]

Gil: I’m so grateful for it, they’re wonderful people and it’s a wonderful show. It just got picked up for Season 21, and it’s still one of the highest rated shows on TV. It’s funny, I think my third job ever I had a little co-star on episode 6 of season one, and twenty years later I got to drive up to Santa Clarita and go back to the same sound stages. It was really kind of surreal.

Lynn: I’ll leave you with a little tidbit from a recent convention where you sang at the Saturday Night Special. There were a lot of new people, and you came out onstage and started singing and I was watching people around me going like oh wow, Gil can sing! They didn’t expect that I guess, so again I felt like a proud mom. Or… Big sister.

Gil singing at the Saturday Night Special

Gil: Well, I appreciate you telling me that because you sense that a little bit from the crowd, but I didn’t know. I can usually tell who’s at their first convention at a photo op or an autograph, and there have been so many new people at every convention, which is amazing. I mean, Supernatural is a classic television show. And Jensen, Jared, Misha, those guys, I mean, they won the lottery. Those characters won the lottery, they’re going to live forever.

Lynn: I’m keeping my fingers crossed for Henry.

Gil: I don’t know what’s going to happen next, but I’m forever hopeful. I’m so grateful that I got to play him, and this was the icing on the cake.

Stay tuned to find out whether ‘The Winchesters’ will return for a second season on the CW, or whether it might find a home elsewhere – along with one Henry Winchester. In the meantime, you can stream the first season on HBOMax!

— Lynn

You can read Gil’s chapter, along with most of

the other Supernatural actors, in Family Don’t

End With Blood (and the sequel, There’ll Be

Peace When You Are Done)- links and info here or at:






One thought on “A Chat With Gil McKinney – ‘The Winchesters’, Cons and The SPNFamily!

  • As a Supernatural fan since the beginning I love Henry Winchester. Gil Mckinney is absolutely gorgeous. I love the way he plays Henry. I was hoping for more Henry. Then came The Winchesters I knew Jensen would give us Henry Winchester back. How could we not get him back. When I heard his voice I was like I know that voice. Then when he appeared I was overly excited. Knowing he can sing to I’m in love. I’m hoping to get to the convention in DC this year and meet Gil. I will be beyond happy.

Leave a Reply