The trend of Supernatural actors in The Boys will continue in season 4 with the connection between the two shows being further cemented. Before overseeing the wild superhero satire The Boys, Eric Kripke created Supernatural which starred Jared Padalecki and Jensen Ackles as Sam and Dean Winchester, a pair of monster-hunting brothers. After the show ended in 2020, Kripke moved on to adapting Grant Morrison’s popular The Boys comic book series. However, he kept his Supernatural connections strong with a number of notable actors from the show joining The Boys.

The main cast of The Boys has become iconic for bringing these comic book characters to life, from Karl Urban as Billy Butcher to Anthony Starr as Homelander to Erin Moriarty as Starlight. Kripke has managed to thrill fans of Supernatural by filling many of these roles with actors they will recognize, bringing the two ensembles together. While some are smaller cameo roles, others have been significant parts of The Boys even after winning fans over on Supernatural.

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Jensen Ackles

Supernatural Character: Dean Winchester / The Boys Character: Soldier Boy

Jensen Ackles is the most notable Supernatural actor to also appear in The Boys. He played Dean Winchester on Supernatural, serving as one of the two leading heroes for the entirety of the show’s run. Going to Hell and back, as well as realms beyond, Dean was a heroic, funny, and charming protagonist with Ackles earning a strong following of fans. After Supernatural ended, Ackles served as narrator for the Supernatural prequel series The Winchesters.

While his role in The Boys might not have been as big as Dean on Supernatural, Ackles became the highlight of season 3 with his performance as Soldier Boy. Seen as the quintessential patriotic “super”, Soldier Boy was seemingly killed in Vietnam only to be found by Butcher and the others and recruited to take down Vought. However, Soldier Boy is worse than Homelander in some ways with no moral code, racist attitudes, and a cold-blooded nature that makes him a memorable villain. Ackles returned to cameo as Soldier Boy in the spinoff series Gen V.

9

Nathan Mitchell

Supernatural Character: Kelvin / The Boys Character: Black Noir

Though his face might not be seen, Nathan Mitchell plays a prominent role in The Boys as Black Noir. Across the episodes, the mysterious, silent warrior became a firm fan favorite. Despite fighting aggressively on the side of Vought International, viewers were won over by the character’s hidden depths. This led to some incredible development in season 3 before ending with his tragic death but Black Noir will return in The Boys season 4 with some big surprises.

Before joining the superhero world, Mitchell had a two-episode recurring role on Supernatural where he played Kelvin, a friendlier and more open-minded angel who briefly aligned with Castiel (Misha Collins). Mitchell first appeared in season 12, episode 15, “Somewhere Between Heaven and Hell.” He later returned for season 12, episode 19, “The Future.” He is the only Supernatural actor to become part of the main cast of The Boys.

8

Lesley Nicol

Supernatural Character: Katja / The Boys Character: Connie Butcher

Lesley Nicol is a very accomplished actor who is perhaps best known for playing Mrs. Patmore on Downton Abbey over the course of six seasons. However, she has also guest-starred on many other shows, including The Boys and Supernatural. Nicol appeared on The Boys season 2, episode 7, “Butcher, Baker, Candlestick Maker.” She played Connie Butcher, Billy’s long-suffering mother. Visiting from England, she tried to facilitate a reconciliation between Billy and his abusive father, Sam (John Noble). Though Billy refused to bury that hatchet, he parted on good terms with his mother.

Years prior, Nichol starred in Supernatural season 10, episode 12, “About A Boy.” She portrayed Katja, the cannibalistic witch from the Hansel and Gretel fable and responsible for briefly reverting Dean Winchester to his teenage self. The move was an amusingly fitting one since Lesley effectively went from playing a butcher in nature to a Butcher in name.

7

Adrian Holmes

Supernatural Character: James Turner / The Boys Character: Dr. Park

Adrian Holmes is another actor who has a strong career outside of these two shows on which he has guest-starred. More recently, fans might know him as Admiral Robert April on Star Trek: Strange New Worlds. Holmes has actually had two separate Supernatural roles. The actor first debuted in Supernatural season 3, episode 15, “Time Is On My Side,” playing an unnamed demon Dean Winchester caught and tortured for information. Holmes later returned for two episodes of Supernatural season 13, playing James Turner, the estranged son of psychic and longtime Winchester ally Missouri Moseley (Loretta Devine).

Holmes has only appeared once on The Boys, in a smaller role in season 2, episode 2, “Proper Preparation and Planning.” He played Dr. Park, the scientist who oversaw the Vought compound that housed Becca Butcher (Shantel VanSanten), and her son, Ryan (Cameron Crovetti). Following Becca and Ryan’s escape, it is unlikely he will return.

6

Christian Keyes

Supernatural Character: Michael / The Boys Character: Nathan Franklin

As well as appearing within the Arrowverse as Neron, Christian Keyes antagonized the Winchesters for multiple episodes of Supernatural. Playing the villainous archangel Michael, the actor debuted in Supernatural season 13, episode 2, “The Rising Son.” Hailing from a parallel, apocalyptic world, he harbored a desire to conquer the prime universe. In pursuit of that end, he recurred across four more episodes before switching bodies to possess Dean Winchester.

Jumping over to the Amazon Prime show, Keyes played A-Train’s (Jessie T. Usher) older brother and coach, Nathan Franklin, in The Boys seasons 1 and 3. A-Train’s redemption arc is largely due to Nathan who encouraged his brother to speak out and fight for the Black community. This is further cemented when Nathan is paralyzed after being assaulted by racist supe Blue Hawk. With A-Train’s story continuing in The Boys season 4, it is likely Nathan will return.

5

Isaiah Adam

Supernatural Character: Forensics Tech / The Boys Character: Lance Corporal Dan Miller

In some instances, the actors who appear in both Supernatural and The Boys might not be overly recognizable to fans of either show. They can appear in smaller roles with the connection between the two series potentially being coincidental. Isaiah Adam briefly appeared in Supernatural season 7, episode 2, “Hello, Cruel World.” There, he played a forensic technician that Dean Winchester encountered while investigating a string of murders.

For the satirical superhero drama, Adam featured in The Boys season 2, episode 1, “The Big Ride.” He seemingly played Lance Corporal Dan Miller, a soldier appearing alongside Homelander and Queen Maeve in a Vought promotional video. However, it was quickly revealed by Stormfront (Aya Cash) that “Dan” was simply an actor playing a role, once again showing the facade created to make these supes seem more heroic than they really are.

4

Kai Bradbury

Supernatural Character: Clerk / The Boys Character: Young Kenji Miyashiro

Bradbury briefly appeared in The Boys season 1, episode 6, “The Innocents.” After the titular group visited Mesmer (Haley Joel Osment), viewers were treated to a series of flashbacks to the early days of “The Female,” a.k.a. Kimiko Miyashiro (Karen Fukuhara). One took place sometime after her enforced induction into the Shining Light Liberation Army. Bradbury played a younger version of her brother, Kenji, to whom she gave her food and sought to protect. That particular storyline thread continued in The Boys season 2.

Bradbury starred in Supernatural season 13, episode 15, “A Most Holy Man.” He played a clerk at a courier company visited by one of that particular episode’s many villains. While neither role is very big, Bradbury’s role in The Boys is linked to the very important and tragic backstory of Kimiko, making it the more important role of the two.

3

Alvina August

Supernatural Character: Tasha/ The Boys Character: Monique Milk

August has been no stranger to The CW, having guest-starred on Arrow and Nancy Drew. In 2017, the actress also appeared in Supernatural season 12’s “Twigs & Twine & Tasha Banes” as the titular Tasha, a powerful and good-natured witch. The character died, was resurrected, and died again over the span of the episode, preventing her from making any subsequent appearances.

Instead, she debuted as Monique in The Boys season 1, episode 7, “The Self-Preservation Society.” As the wife of Mother’s Milk (Laz Alonso), Monique was forced to go into federal protection and later divorced M.M., marrying Todd instead. The character returned in season 3 with her storyline getting more interesting thanks to Todd becoming a fervent supporter of Homelander. However, for unknown reasons, August didn’t reprise her role with Frances Turner taking over the part.

2

Jim Beaver

Supernatural Character: Bobby Singer / The Boys Character: Robert A. Singer

One of the most notable Supernatural actors in The Boys, Beaver initially made a surprise cameo on the Amazon Prime series. As Secretary of Defense Robert A. Singer (the name being a Supernatural reference in itself), the veteran actor shared a scene with Madelyn Stillwell (Elisabeth Shue) in The Boys season 1, episode 8, “You Found Me.” Beaver later reprised the role for The Boys seasons 2 and 3. Season 3 revealed that Singer, going by the folksy nickname “Dakota Bob,” was running for President with secret supe, Victoria Neuman, as his running mate, suggesting he has a role to play in season 4.

Before that, he enjoyed a long-serving, fan-favorite role on Kripke’s previous show. As the lovably crotchety Bobby Singer, the actor debuted in Supernatural season 1, episode 22, “Devil’s Trap.” A Winchester family friend and fellow hunter, he recurred throughout the overall 15-season run, bouncing back from several deaths and even guest-starring in Supernatural‘s series finale.

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Jeffrey Dean Morgan

Supernatural Character: John Winchester / The Boys Character: Joe Kessler

Also very well-known for playing Negan on The Walking Dead, Jeffrey Dean Morgan played the Winchester brothers’ estranged hunter father John Winchester in many episodes of Supernatural over the years. Though not exactly an antagonist, John isn’t always the good guy either, as he spends most of the show pushing Sam and Dean to their emotional limit. However, he was a fan-favorite aspect of the show, which doesn’t make it surprising that he was also invited to join The Boys.

The Boys season 4 will see the debut of Morgan’s character. Joe Kessler. Though not much is known about the character, the trailers for The Boys season 4 have shown that he is an ally of Butcher with the two sharing a past. Kessler also seems to see the supes as the very real threats the same as Butcher does. Morgan has been confirmed to appear in multiple episodes in the new season of the show.