Jensen Ackles as Dean Winchester looking sad in Supernatural and Soldier Boy looking angry in The Boys

The Boys often features actors from Eric Kripke’s former series, Supernatural, but it looks like the most exciting reunion is now impossible — and as a fan of the CW show, I’m devastated about it. From minor stars to more recognizable players, many Supernatural actors appear in The Boys. Black Noir actor Nathan Mitchell and Splinter star Rob Benedict will both be familiar to fans of the CW show, and Jim Beaver’s Robert Singer even references Supernatural with his name.

These are just a few of the characters from The Boys who are played by Supernatural alum, and it’s great to see them working with Kripke again. It’s also fun to see them interact with one another, though this doesn’t happen as often. But Gen V‘s gross Supernatural reunion made me appreciate the overlap between the two shows, and I felt for sure that The Boys season 4 would be able to top this moment. Unfortunately, the Amazon series’ latest twist makes the most exciting reunion impossible — though there is another team-up that could fix this in The Boys season 5.

Jeffrey Dean Morgan & Jensen Ackles Can’t Reunite On The Boys Now

The Show’s Joe Kessler Twist Makes Their Supernatural Reunion Impossible

Jensen Ackles as Soldier Boy in The Boys Season 3 raising his eyebrows at someone while outside

Jensen Ackles holding his shield and frowning as Soldier Boy in The Boys season 3

While there are many noteworthy Supernatural actors in The Boys, Jensen Ackles and Jeffrey Dean Morgan are some of the most exciting additions to the show. Ackles makes his debut as Soldier Boy in season 3, and Morgan enters the fray in season 4 — though the latter’s character isn’t quite what he seems. Although Morgan’s Joe Kessler is introduced as Butcher’s old friend, The Boys season 4 reveals he’s actually long dead. Butcher is hallucinating images of Kessler, just like he’s conjuring visions of Becca. Unfortunately, this limits Morgan’s role in The Boys going forward.

Since Morgan plays Ackles’ on-screen father in Supernatural , I was hoping to see them reunite in Kripke’s superhero series.

It also means that the John Winchester actor will never get to interact with Ackles’ character in The Boyssomething I’m pretty disappointed about. Since Morgan plays Ackles’ on-screen father in Supernatural, I was hoping to see them reunite in Kripke’s superhero series. It would have been particularly interesting to see them on opposing sides of the conflict, as Kessler harbors a hatred of Supes in The Boys. Such a dynamic would be a nice change of pace from their father-son relationship in Supernatural, but it can’t happen with Kessler dead.

Even A Kessler Flashback Can’t Save The Boys’ JDM & Jensen Ackles Reunion

Kessler Would Need To Be Recast For An Earlier Scene Between The Characters

Karl Urban looking confused as Butcher in The Boys and Jeffrey Dean Morgan as Joe Kessler in season 4
Custom Image by Yailin Chacon

The only way Kessler and Soldier Boy can still interact in The Boys is through flashbacks, and even an earlier scene between the characters can’t save Morgan and Ackles’ reunion. Kessler would have been around 18 years old when Soldier Boy was captured in 1984, which makes the idea of them interacting unlikely. But even if The Boys could find a way to push them together, it would need to recast Kessler to do so. An 18-year-old Kessler would look much different, making it difficult for Morgan to portray the character in a flashback with Soldier Boy.

Having a younger Kessler interact with Ackles’ Supe just wouldn’t be the same, as it would eliminate the excitement of seeing the Winchesters on-screen together again. It looks like anyone hoping for a moment between Morgan and Ackles will need to wait for them to appear in another project with one another. However, an even more exciting Supernatural reunion is possible in The Boys season 5 — and I think it would make up for the fact that Morgan’s and Ackles’ characters will never meet.

Don’t Panic, There’s A More Exciting Supernatural Reunion Ahead In The Boys Season 5

The Winchester Brothers Can Still Team Up In The Final Season

Jared Padalecki as Sam Winchester in Supernatural and Jensen Ackles as Soldier Boy in The Boys
Custom image by Simone Ashmoore

While Ackles will likely never share the screen with Morgan in The Boys, he may get the chance to team up with another one of his Supernatural co-stars in season 5: Jared Padalecki. Comments from Kripke suggest that Padalecki will have a cameo in the show’s fifth and final season, and the Supernatural alum has responded positively to the idea of making an appearance. If Padalecki does show up in The Boys, the Amazon series needs to bring him and Ackles together on-screen. After all, they’re the two biggest stars associated with Supernatural, and fans are eager to see them reunite.

If Padalecki does show up in The Boys, the Amazon series needs to bring him and Ackles together on-screen.

The Winchester brothers teaming up — or even opposing one another — would be a great way to honor Kripke’s CW series in The Boys. With Ackles’ character back in cryosleep, it certainly seems possible, but it will all depend on who Padalecki plays. Either way, The Boys season 5 has another chance to deliver a top-tier Supernatural reunion, even if season 4 failed to do so.