Where It All Began – Return To Supernatural Chicon!

Chicago was the very first Supernatural Creation convention, way way back in 2007. My friends and I stalked their website for weeks waiting for the tickets to go on sale, trading off ‘watch the site’ times so it would always be covered. We were rewarded with front row seats, back in the day when front row was the same price as the rest of the gold tickets, and had an amazing time at that very first con. I’ve been extremely fortunate to be able to return to what we then called “Chicon” each year it’s been held since then. It’s where one of my closest friends lives, so it also means I get to hang out with Winchester Family Business editor Laurena and her lovely husband. This year I had lots of other friends, both old and new, there too – so it was a whirlwind weekend of patio dinners at great restaurants in the 75 degree sunshine and long talks in the vendor room with friends I don’t get to see nearly often enough.

If you’ve ever wondered what the vendor table looks like, this was the Chicago set up – if you’re ever at a con, come say hi! I’m always happy to sign books too, whether you’ve brought them with you or bought them at the con. And if Family Don’t End With Blood inspired you in some way, it makes my day to hear about it – and the actors’ when someone says the chapters they wrote were an inspiration.

My flight got in on Friday, so I missed DJ Qualls and Julian Richings (my friend Barb caught a few photos for me).

I got to chat with Julian a bit later – we both worked on the book ‘Death in Supernatural’, with Julian writing the Foreword and me writing the Afterword, so it was nice to see him and catch up.

I caught Gil McKinney and David Haydn Jones panel in progress. The pairing of Gil and David might seem like an unusual one, as their characters didn’t interact at all on Supernatural, but they have gelled into a delightfully naughty duo that I thoroughly enjoy. When I came into the ballroom, they were trying to decide if Gil once wore his dance belt backwards, or was it really just a thong?

David has a new movie coming out that apparently involves dancing, so that is sure to be fun!

Gil talked about a film he was in called Metamorphosis, which they shot on a private island off Canada. Oh, and he wore a dance belt… lol

And another time when his character was supposed to piss himself and Gil decided to go all method and do it for real – that’s dedication!

David: So watch the movie Metamorphosis. Or just check out Gil’s Only Fans account… lol

Gil also told the story of the time he was on CSI in bondage gear and assless chaps. Which I somehow tweeted as “assless chaos”. I’m sure the assless chaps did cause chaos tho.

David: Gil and I are writing a fanfic…

They got some more serious questions about the show. Here’s Gil gamely trying to answer a canon continuity question about Henry Winchester…

David: Is someone keeping a record of Supernatural canon inconsistencies? Or is it all just the multiverse now…

Me: Don’t go there…

On a more heartfelt note, Gil said that Supernatural really did change his life. You can read his story of how in the chapter he wrote in Family Don’t End With Blood – and about how the same is true for David in his chapter in There’ll Be Peace When You Are Done.

Gil said that when Jensen Ackles called about him reprising his role on The Winchesters, he was so excited.

Gil: I always wanted to play Henry again. Ten years later getting to play Henry Winchester again was a dream come true, and working with Drake Rodger was amazing.

David agreed about what a gift Supernatural was.

David: Ketch was such a gift. It was originally only three episodes.

Who else would they like to play?

David: I would love to play Crowley, but no one can play him like Mark Sheppard!


Richard Speight, Jr. was back as our emcee again, which is always awesome. He makes us all laugh, which is one of the most therapeutic things about cons.

Kim Rhodes and Briana Buckmaster were up next, Briana sporting a new haircut which looked fabulous. For the new fans in the audience?

Kim and Briana: By the way, we curse a lot…

Kim talked about the characters she’s played and the people she’s worked with, both on Supernatural and on The Suite Life of Zach and Cody.

Kim: I’ve been so lucky to not have to manufacture love for the people my character loves.

Both expressed gratitude for Supernatural and the unique supportive  atmosphere on that set.

Kim: Jared and Jensen created an environment where everyone knows they’re free to do their best.

Briana: They welcomed me in like I was an old friend.

As someone in a family with lots of neurodivergent people, I always appreciate Kim sharing her own experience.

Kim: What my autism diagnosis gave me? Permission not to suffer for what society says. My needs are real.

Damn right.

In response to a question about who they fangirl, which inevitably included Neil Gaiman for Kim, Briana sang the song she wrote as a young teenager for Jonathan Taylor Thomas.


Barb took a few shots of Kim and Briana from their other panel that I missed too – love Briana’s outfit!

Friday night was a lovely outdoor dinner with my old friend Laurena and new friend Sadie  from the Defense of Fandom podcast. We talked all things Supernatural and especially the history of this long-standing fandom that I’ve been in from the start, since Sadie is relatively new to the madness. Then we went to karaoke – DJ Qualls is doing an amazing job making it special and keeping the energy level up (with some help from DJ Liz of course)

We all got the news that The Winchesters had been cancelled in the middle of the convention, so The Winchesters panel with Meg Donnelly, Drake Rodger and JoJo Fleites on Saturday was a bit emotional. The three got lots of questions about the show and its retro style.

JoJo: Our costume designer was very collaborative in creating wardrobe. My own style is actually not far from Carlos and the 70s.

Drake’s maybe not so much.

Drake: Oh yeah, I had lots of choices for John’s wardrobe too… light blue flannel…dark blue flannel… lol

Drake was a fan of OG Supernatural, and sometimes his takes are a bit dark like those early seasons – which I personally love. A fan asked where they would have taken The Winchesters if they got renewed.

Drake: I would have had the story go very dark, like three years of pain and torture. The season 1 fans would hate it.

Me: But some OG Supernatural fans would love it!

Meg disagreed.

Meg: My idea for the future of the characters is all rainbows and happily ever after…

Me: Noooooooo

JoJo: I would have loved to see Carlos be the hunter that gets out and has a family. Also I’d love him to be related to Rowena!

I can totally see that.

Drake hypothesized about The Winchesters and what it ended up being all about, saying maybe Dean finds out that that was the best version of their story, and messing with it makes it worse!

If they played other characters from the mothership, Drake said he’d love to play some version of Sam. He reminds me of a young Jared Padalecki, so I can see it – and not in a fandom wanky kind of way!

They all have been having a great time doing conventions.

Meg: Smallville Nights at cons is so fun with Tom Welling and Michael Rosenbaum. One time Jensen Ackles crashed it and was like, I could’ve played that role!

The three cast members have clearly become close during filming of the show and after. JoJo and Meg took Drake to see Wicked.

Drake: I felt like I was having an acid trip!

JoJo confided that they love Queen, and Meg confided that she loves K Pop.

Drake confided that he didn’t act until he was sixteen. He comes from a blue collar family where “guys play sports”, and it took him a while to break out of that. Also he has pretty severe dyslexia.

Drake: And yet I chose acting!

That’s pretty inspiring actually.

JoJo is also pretty inspiring. When they were in school, they played Ursula in a play.

JoJo: I identify as non binary now, but at the time it was scandalous. But I shut up all the haters!

Damn right.

They also had some stories from filming The Winchesters, like the time Meg was practicing a roundhouse kick and connected for real – with Drake’s face!

Drake loved the Vietnam flashback scenes. So did Jensen, who was on set – and shared the dailies proudly with Rob Benedict at the next con.

At some point in this busy day, I missed Gil McKinney and David Haydn-Jones in a suit, so here are Barb’s photos of that:

And then, because it was Saturday, it was Misha time! He had just returned from a visit to war-torn Ukraine.

Misha: To those who are Ukranian here, I’m so sorry for what’s going on in your country, but it was remarkable to see how an entire country can rally around a cause. Everyone in Warsaw has opened up their homes to refugees and it’s so inspiring to see.

He also talked about being inspired so much by his friend, Giles Duley.

(For those of you who read the email I got from a Supernatural fan in Ukraine who has been fearlessly helping get women and children out of the war zone – and taking inspiration from the chapters written in Family Don’t End With Blood – I did email it to Misha and he was as touched as I was. Supernatural has made a difference in so many ways.)

On a lighter note, someone asked him about pick up lines people have used on him. Oddly.

Misha: A pick up line people have used on me is ‘did it hurt when you fell from Heaven?’  And no, it doesn’t work.

We all have comfort movies (and shows, ie Supernatural for me). Misha does too.

Misha: The movie I’ve watched the most times is The Man Who Knew Too Little, with Bill Murray.

Misha, like most of the cast, looks back on Supernatural fondly.

Misha: We laughed a lot on Supernatural, and those are some of my favorite experiences.

Like everyone else on the show, the collaboration was important to him.

Misha: I was part of a team that worked really well together on Supernatural, like a well oiled machine.

He said that his last scene on Supernatural was an intense emotional experience, for multiple reasons. (Not only for what Cas said to Dean, but in part because it was his last scene, and thus his goodbye to the show and his crew and castmates).

Now that GISH has ended, he was asked about any GISH mistakes.

This is him reenacting a GISH mistake of someone being tangled in Christmas lights. On a rooftop.

Misha sometimes gets very odd questions. There was one about what you’d do if you could do it with half your brain awake (since some animals can do things with half their brains sleeping apparently).

Misha: Oh, this could get kinky…

He also told the hilarious story that I’ve heard before about when he was up for the role of Anakin Skywalker, but he was strictly not allowed to tell anyone about it. He went up to Skywalker Ranch and met with George Lucas and was so excited, he was dying to tell someone. So he told a random server at a pizza place he stopped at.

Random guy: My cousin is Natalie Portman.


And then, in typical Misha fashion, he treated the whole ballroom to pierogis – which, by the way, were delicious! This is not the first time I’ve been in the audience when Misha brought us all treats. It’s always chaos, but also heartwarming in a uniquely Misha way.

Misha: Come on up and get some!

Does he miss Supernatural and would he want to be in a reboot if there is one?

Misha: I really hope there is a Supernatural reboot, and yes, I’d like to be in it. I mean, at least a little goodbye few episodes… you know, maybe ten seasons…


At the time of this con, Gotham Knights had not yet gotten the bad news of being cancelled. Misha talked about how challenging it was to play two versions of himself in that show.

When Richard came out to end the panel, he immediately went into the “song of the con”, which is the advertising jingle for 1 877 Cars 4 Kids, which is stuck in everyone’s heads even now. He tried to get Misha go to along with it, but was met with admirable resistance.

We also got a Ruth Connell panel on Saturday afternoon – I’m in love with her outfit!

Ruth gave Misha props for the pierogis, and then reminisced about the time at Comic Con when Misha fed the lines of fans waiting to get into Hall H the next day. I was hanging out with Osric Chau that day, so when Misha called to ask Osric for help I ended up helping out too. You don’t know chaos until you’ve followed Misha Collins through the French Quarter to a far off pizza place and then carried the pizzas down the hill with him leading our little line of helpers like the Pied Piper. Everyone in line was so grateful and it really was a wonderful experience, and pure Misha benevolent chaos.

Ruth said that the general kind of “witchiness” we have as people has become more popular recently.

Ruth: So it’s become more important to me about Rowena over time.

She also understands Rowena’s bond with the Winchesters.

Ruth: Here are these people called the Winchesters, who understand her world. After her son died, she uncovered some vulnerability.

I loved that part of Rowena’s arc – it was subtle, happened gradually, and made sense to me.

Ruth: I was so satisfied for Rowena and the fandom that Rowena got to be the boss. She’s down there making Hell great again (smirk)

She also said it was wonderful playing the same person for six years, and that she’s learned so much from fans about all the characters.

Ruth: It would be wonderful to have that same experience on my new show, Dead Boy Detectives. The Night Nurse is very different than Rowena. Rowena changed my life, but I’m enjoying playing her too.

Rowena also appeared in an episode of The Winchesters.

Ruth: Maybe Rowena was looking for Crowley in The Winchesters for a different reason…hmmm…

She also expressed her appreciation for conventions, and the intrinsic value doing something like coming to conventions for FUN, which I appreciated!

We also got an R2 – Rich and Rob – panel. Rob said he liked all the versions of Chuck that he got to play and is grateful he got to play him for so long.

Richard agreed.

Rich: It’s great to be able to play different versions of a character over time, and we could also add our own nuances.

Rob: I knew during Swan Song that I was God, the creator in the show – like Kripke was the creator.  At the beginning, the writers didn’t know Chuck would be God. Andrew Dabb said they’d ask themselves, are we those guys who’d make God the writer? Yes, yes we are…

Fandom: —

They are inevitably hilarious in their own unique way.

Rob: We’re from states that touch each other.

Rich: And yet we don’t touch each other…

Rob: It seems that I once had an unhealthy attraction to his wife.

Rich: And I hooked up with his girl (Ruth)…on the show!

At one point Richard sang one of his favorite songs, “Up Robbie’s B-Hole” while Rob giggled.

And if you haven’t listened to Rob and Rich’s Supernatural Then and Now podcast, check it out!

Saturday was another delicious dinner on the patio of a great restaurant in the perfect weather with friends – what better?  And then, it was Saturday Night Special time!

Creation’s Stephanie Dizon joined the band for Seven Nation Army.

Kim Rhodes was adorable.

And rocked out, as always!

Gil McKinney let his inner rockstar out – and no, that isn’t a third leg even though hilariously it looks like it. Gil’s response to my tweet of this photo:

Gil: WTF


Jason and Rob (and the audience) all made some beautiful music and harmony with Hallelujah.

When Briana Buckmaster sings ‘Hold My Halo’ you damn well believe it.


We got a special treat with Richard Speight, Jr. joining the fun with Copperhead Road.

I love when he sings that, and anyone who hasn’t heard him sing before kinda goes, OH!

Billy Moran’s hair was on point, btw.

Temporary Billy Moran hair appreciation post…

And a Borja and Norton appreciation post too!

Oh heck, let’s toss in some rockstar version Rob Benedict too…

We also got what’s a special treat for me at least – a beautiful rendition of the classic ‘Medicated’.

With kazoos!

And an encore that had everyone on their feet.

And then it was Sunday – J2 day!

I missed having Jared at the last con (though it was wonderful to have Jeffrey Dean Morgan there instead) so I was extra happy to see ‘the boys’ onstage together again. They seemed to appreciate it too.

Within about a minute of the gold panel beginning, we had a Jensen double entendre, so you could tell it was gonna be a good panel.

They did their old man shtick when confronted with someone who was at the very first Chicago con back in 2007 – when she was TWO.

(I also groaned. I was there too. And I was NOT two.)

Jensen was in a particularly good mood because of his Wordle victory earlier in the day – he and Jared and some of the other cast have an ongoing Wordle thread and Ackles clearly couldn’t wait to share his good news with them.

Why is that so cute?

Also, uhhhh, Jensen’s arms are distracting. In a good way.

They talked about wanting to get back to making more Supernatural sooner rather than later – while they still look like Sam and Dean!

(I’m not gonna argue, though boys, you look just FINE imho)

Side note: Damn, it was good to see Jared with his hair Sam-like long and not slicked back. As Jensen once said, let the beautiful hair be free (or something like that).

On Supernatural, they said it would have been great to have Jeffrey Dean Morgan on more, but it was also great to get to see Sam missing his dad.

Jensen agreed, talking about all the people they were glad to have on the show, and saying there were a lot of people they’d love to have back.

Jensen: But ultimately, it was a story about two brothers, and it came back to that.

There was a hilarious little bit where they joked about how different things would have been if Dean had just put a backpack on before the brothers went into the barn.

Jensen (as Dean): Whew, that could have been bad!

I love that they can both joke about the barn scene and also talk seriously about how despite its sadness it’s a favorite for them both.

Sometimes the questions are….creative. What Sesame Street characters would they be?

Jared: Big Bird.

Jensen: Oscar the grouch.

(Of course)

They also got weirdly serious at one point, Jensen theorizing about known existence.

Jared: This is what we were talking about last night – and why you don’t want to be friends with Jensen!

Everyone in the audience: Actually…

Every single time I watch a Jared and Jensen panel, it’s such a serotonin infusion, because they spend so much time just enjoying each other’s company and laughing together. This panel was no exception, which is really saying something since they’ve been doing this since 2007! (When I was there at the very first Chicago convention…and was not two….)

One of the most moving moments was when Jared and Jensen recalled a fan coming to the set with her family for Make a Wish, dealing with cancer. It meant a lot to them, that they could provide that escape for a little while from dealing with something like that.

Eric Kripke recently tweeted about how many fans he’d met on the WGA picket line who told him what Supernatural had meant to them, and this reminded me of that. When I say the show was life changing, it literally was. Is.

We got a Ruth and Rob panel in the afternoon – they have to be one of the most adorable couples ever, seriously.

A fan actually asked them, Sam or Dean? They were smart enough not to answer.

Rob: That’s like asking Chuck to choose between his favorite children!

Ruth talked about Rowena’s close relationship with Sam, saying she was a little afraid of Dean.

Ruth: Sam and Rowena have a trauma bond.

Ruth told a funny story about taking a tour of the jazz museum in New Orleans and someone asked who they were.

Ruth: I said from Supernatural and they were like oh, those two tall guys?

Favorite moments on the show?

Rob: When I got to sing Fare Thee Well on the show.

Weirdest questions?

Rob: The first time I walked onstage and Chuck got booed

Ruth: When I get, ‘oh you’re so much prettier in real life’…

Chuck’s dream day?

Rob: Just to be forgiven by Sam and Dean….back at the bunker, hanging out…

Poor Rob, he’s got some Chuck PTSD.

Then we got a Walker panel, with Jake Abel, Keegan Allen, Jeff Pierre and Mitch Pileggi.  This is a cast who also enjoys what they do and each other, so there was lots of joking around and laughter.

Keegan got asked about his former fan favorite show, Pretty Little Liars.

Keegan: PLL was heightened reality; Walker is more based on reality, and family oriented.

On Liam’s PTSD…

Keegan: We worked hard on that, and I worked a lot with Jared, who gave input.

Jake: PTSD, is that post Toby syndrome?

Keegan always has his camera, and Mitch talked about him taking photos on set.

Mitch: There’s a lot of attractive people on Walker, so it’s always a photo shoot!

Jeff got asked about a love scene he did with Nina Dobrev, which he remembered fondly.

Jeff: We did take after take after take…

Mitch has good stories. He said when he had to pick up Keegan, they used a crane.

Keegan: Are they trying to tell me something??

As far as what’s to come, Jeff didn’t totally answer a question about Trey and Cassie. If you read my reviews of Walker, I’ve been worrying that the show is going to pair them up romantically, which I’m not a huge fan of.

Jeff: Trey and Cassie are friends first, and I don’t know if they want to complicate that…but there are feelings there…

Me: Hmmmm.

Everyone talked about what a wonderful set Walker is to work on, giving credit to Jared.

Jake: It’s difficult to come onto an established show as a guest star. The most welcoming shows I’ve been on have been Supernatural and Walker.

Mitch is a big Jared fan.

Mitch: I’m not intimidated by Jared, we mess with each other. He asked me to treat him that way in front of the other cast too, so they’d treat him like fellow cast, not an EP.

Jake talked about collaborating with Richard Speight Jr. on Supernatural.

Jake: When you’re playing a bad guy, don’t tip the hat. I asked director Speight if we could not do an eye flare going between Adam and Michael.

(And it worked!)

Surprise Richard Speight, Jr. agreed!

Jared and Jensen were running behind, or having too much fun catching up, or something, so Richard’s panel ended up being before the J2 panel.

Someone asked him about fanfiction – which made me laugh remembering when Kathy and I first me Richard back in 2008 and asked him about fanfic, which we then had to explain entirely. He was dumbfounded, but even then I think he appreciated the creative part of it.

Richard: I think creativity is great. We portray these characters and it’s awesome that people are inspired by it.

He’s grateful for being able to play the Trickster and Gabriel for so many seasons of Supernatural.

Richard: It’s a thrill to get a character to play with that much backstory. There wasn’t a lot of improv, there was more in The Winchesters when I was in that.

He went on to say that he thought the dialogue they wrote for Loki was great, and that he added his own touches for The Winchesters. He also said it was Loki that he played in that show, but not the same Loki as he played on Supernatural. The whole AU thing makes my head hurt!

And then it was finally J2 time!

They did the jump a little differently because of Jared’s bad knee – Jensen gave him a fistbump side hug for being good and not actually leaping like he always does. Get that knee fixed, Jared!

He said he actually is getting his knee examined while he’s in Chicago, which Jensen and everyone else are very happy about.

People will ask Jensen how he felt about Dean’s death until the end of time, I’m guessing, even though he’s clarified a hundred times (He had a hard time just with the idea of Dean dying at first because he’s so close to the character, but he loved the finale and the actual scene).

Jensen: When important characters die, it’s hard, but it makes for good storytelling.

Jared: On Supernatural, anyone can come back to life. Let’s hope the boys ride again!


Jared told the adorable story of meeting Gen on Supernatural, then did this, even more adorably.

Jared: If you like it then you gotta put a ring on it!

They love nothing more than to reminisce about their time as Sam and Dean. This panel it was Yellow Fever. Apparently the snake wrangler was a big Supernatural fan.

And Jensen will never get over that Jared immediately ran out of the room haha.

They also never get tired of giving each other props, and genuine admiration.

Jared: Jensen was a natural as a director.

Jared: Actually, he was supernatural…

With a dad joke no less!

Someone asked about bucket lists, which somehow turned dirty.

Jensen: I don’t have a bucket list.

Jared: A bucket…fist?

Jensen: 0—0

It continued down that lane, much to my great delight.

Jensen: I wear a beard balm called spiced wood.

Jared: He likes wood on his … you set yourself up!

They reminisced a little about filming the early episode Dead in the Water too, saying that they had a hot tub to jump into between scenes in the lake because it was so cold.


And about All Hell Breaks Loose too, when Jensen got a little overly enthusiastic about Dean being thrown into the tombstone and hit his funny bone on it.

Jared: Did you laugh?



The funniest part of the panel was when Jared and Jensen attempted to recall something from every season of Supernatural, with truly hilarious results.

When they got to Season 14, Jensen re-enacted a bit of that aerial fight scene that…. Uh, didn’t go so well. Jensen recalls what he was saying to himself…

Jensen: This is it, we’ll never work again… Bob Singer, behind the monitor: this is it…

Jared: This is it, he’ll never work again.

Why are they so funny??? But seriously, I love that they love and value the show and their characters so much, but they’ve always been able to laugh at themselves too.


They also reminisced about all the times they got in trouble for playing with the props.

Poor Robyn.

I suppose it’s not surprising that they still dream about each other after all those years of being together so much.

Jared: I was on vacation last week with the family, and I had a dream I was playing rock paper scissors with Jensen!

The last question fan asked them what they did for self care.

Jensen: Even when we worked late, Jared would get up and run. I just kept busy.

The panel ended with the traditional J2 fist bump – and then the band and Richard broke into the (unfortunate) theme of the con, singing 1-877-Cars-4-Kids to Jensen’s utter confusion. Which was adorable.

Complete with Rich’s guaranteed-to-make-Jensen-grumpy dance lol


Jared and Jensen said their goodbyes and thanked the fans.

And that was the end of Chicago Con 2023! I actually caught the longstanding traditional “It’s the end of the con as we know it….so go home” from the band and Richard.


It’s hard to believe I’ve been going to this con since 2007. Feeling very grateful.

The evening ended with a lovely dinner on the patio of the restaurant across the way with my friend Laurena and her lovely husband. I stayed in town on Monday to spend more time with Laurena and do lots more patio eating and drinking in the gorgeous weather. This is a good time of year to have a Chicago con, just saying! (Next year’s is November, oh well…)

Before I go, a bit of news! If you haven’t seen the announcement yet, we’ve got a new book coming out in October 2023 – it’s a deep dive into the hit Prime Video show ‘The Boys’, with chapters from psychologists, sociologists and media experts about what makes those complicated characters tick and how the show gets away with challenging alot of things that are a problem in real life. Plus exclusive interviews with Jensen Ackles, Jim Beaver, Aya Cash, Nathan Mitchell and the co-creator of the comics, Darick Robertson.

If you preorder now you’ll also get some beautiful bonus original art of Kimiko and Soldier Boy! Order at:  https://smartpopbooks.com/theboys/

Stay tuned for more!

Additional con photography courtesy of Barb LeVan – thanks so much!


You can read about how special Supernatural

Is to the actors and the fans in Family Don’t End

With Blood and There’ll Be Peace When You

Are Done, links here or at:

















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