The Boys Season 4: Why Joe Kessler Looks So Familiar

"The Boys" Season 4 will feature real-life politics and murderous sheep, in addition to some all-new recruits joining both the supes and our swear-heavy heroes. While Homelander (Antony Starr) enlists the extra power of Sister Sage (Susan Hayward) and Firecracker (Valorie Curry), Butcher (Karl Urban) finds a new advantage in an old ally by the name of Joe Kessler. In the comics, Howard Kessler aka The Monkey debuts in the first issue and is caught under Butcher's boot during his time as a CIA analyst. On the show, Kessler is far more of a no-nonsense former covert buddy of Butcher's, which is far more believable given that he's played by none other than Jeffrey Dean Morgan.

A staple of the big screen as much as the small, Morgan has breathed life into some of the most iconic characters in popular culture. From heroes to villains, he's done it all, sometimes dropping into a show halfway through to give it a surprising jolt that fans didn't know they needed. Earning that reputation has come from some impressive performances. Morgan has filmed more comic book projects than you probably realize ... but not before he sent viewers into tears as the perfectly loveable patient on "Grey's Anatomy."

"Grey's Anatomy" has seen plenty of heartache, but perhaps none endured more on "Grey's Anatomy" than Jeffrey Dean Morgan's Denny Duquette, Jr. This poor guy needs a new heart, gets it replaced, marries his doctor, and then breaks her heart after he dies from a stroke. Morgan turned the charm up to 11 wooing Izzie Stevens (Katherine Heigl) from the comfort of his hospital bed. Unfortunately, it wasn't meant to be when he was killed off with a death that even led the show's creator, Shonda Rhimes, to cry while writing it. Morgan was fully aware that the show's popularity was booming with every season and did everything he could to stick around on the drama.

Speaking to Sean Evans on Hot Ones, Morgan acknowledged his time on "Grey's Anatomy," saying, "That character, Denny, and that love story with Izzie kind of took the world by storm. I knew how f—ing lucky I was to be there." When it came time for his character to kick the bucket, Morgan pleaded for a rewrite. "I was like, 'Please don't kill me! I will do anything.' I did. I begged her." Even so, the actor was grateful for the part that paved the way to his next big role. "Being Denny, where I never got out of bed, is why Zack Snyder hired me to be the Comedian [in 'Watchmen']. That's how special that was."

In Zack Snyder's impressive film adaptation of Alan Moore's acclaimed "Watchmen," Jeffrey Dean Morgan's bitter-humored scumbag and so-called hero, the Comedian, is a far cry from his heartbreaking role on "Grey's Anatomy." The highlight of his character is in the film's opening, when he is brutally beaten and gets thrown from a window. One of the actor's only issues with the part is just how little the Comedian is able to defend himself in the throw down that leads to his demise.

"The big fight with me is just a series of taking punches. I didn't get to land one, and I'm still mad about that. I was like, 'Just let me hit him once, for crying out loud," Morgan recalled to MTV. "We did so much training. I was in Vancouver for two months before filming just to work on that fight, and it was just how to take punches and apparently not hit anyone." Unfortunately, the rare occasions where the Comedian does overpower his opponent happen during the harrowing scenes opposite Carla Gugino as Sally Jupiter. "We took no prisoners in anything in this movie ... We made it as real as we possibly could, the fight scenes in particular," Morgan said. "They're not pretty fight scenes or stylized. Especially the Comedian or Rorschach. These guys would bite you just as soon as kick you in the balls."

Continuing his stint as a star of comic book stories, Jeffrey Dean Morgan played Clay in this now overlooked action-packed entry that features a handful of Marvel stars-in-the-making. "The Losers" is a classic tale of a double-crossed team getting even after one of their own (Idris Elba) leaves them for dead. After being the smarmy, cigar-chewing scumbag in "Watchmen," Morgan brought the balance of a bad good guy worth backing in an "A-Team" like adventure. But while "The Losers" might not stand among the best comic book stories brought to life over the last two decades, it's clear that Morgan already had his finger on the genre's pulse and was hungry for more.

Speaking to ComicBook in 2010, the man that would be Negan and Kessler (to name a few) was all for diving into comic book stories. "It's kind of an untapped world, this comic book world. I read the same scripts over and over again and comic books are just apt. There's this big, wide universe out there," said Morgan. "If you've seen the stuff that has come out and the stuff that they're making, it's a trend that's going to continue for a while. I'm happy to be in this world. I'm loving it. I love this. I could do comic book movies forever." Let's just be grateful he got his wish.

There are plenty of plot threads in the DC Extended Universe that never came to light, but one that a lot of viewers were keen to see was Jeffrey Dean Morgan becoming a Dark Knight himself. In Zack Snyder's "Batman v Superman: Dawn of Justice," Morgan starred alongside "The Walking Dead" co-star Lauren Cohan as Thomas and Martha Wayne, reenacting their iconic demise. The appearance sparked rumors and just flat out fan excitement for Morgan to potentially be a part of adapting DC's "Flashpoint" event, which sees the Flash change time, leading to Bruce Wayne being killed in Crime Alley and Thomas taking up the mantle of Batman instead.

Speaking to CinePOP in 2021, Morgan admitted he'd always had his eye on the Bat and was open to the alternative iteration that is far darker than the one we'd come to know. "At the top of my list has always been Batman, that's always been my favorite superhero. And talking about 'Flashpoint' has been very fun, I get asked about it a lot. I love the story of Flashpoint Batman. Who knows? Who knows with DC? Who knows with how these franchises work?" Unfortunately, it was a gig that Morgan never got. Perhaps, in another timeline, Morgan's Thomas Wayne is a more callous caped crusader and absolutely killing the role like we know he would.

Long before Eric Kripke was having superheroes perform heinous acts behind closed doors on "The Boys," he was sending two brothers off to fight evil across an almost unthinkable 15 seasons on "Supernatural." During that time, Sam (Jared Padalecki) and Dean Winchester's (Jensen Ackles) dear old dad, John (Jeffrey Dean Morgan), occasionally drops in on them. Appearing on 13 episodes, the bond between father and sons worked so well that not even death could sever it. In turn, a strong enough relationship was formed between Morgan and Kripke that when the time came, the former asked his old work buddy for a spot on "The Boys," which is how he ended up as Kessler.

Speaking to Parade in 2024, Morgan explained, "I watched the first couple of episodes of 'The Boys' from Season 1 and kind of flipped out because I'd never seen anything like it. That's saying a lot, because in this day and age, so many shows are just a repeat of something else," he admitted. "So I went on about it on social media, and Eric saw it. I knew even if I just did one episode, I would be happy." Thankfully, he's got a few more than that, which is an impressive feat given his busy schedule on the other comic book adaptation he's been on since 2016.

Say what you will about his arrival on "The Walking Dead," but Jeffrey Dean Morgan's Negan has become as integral to the franchise as any other of your favorite survivors who have made it a routine of aiming for the head. Of course, his first target makes him an enemy of Rick (Andrew Lincoln), Michonne (Danai Gurira), and especially Maggie (Lauren Cohan), but then Negan goes on a rocky road to redemption that led to the spin-off "The Walking Dead: Dead City."

Pairing Negan up with Maggie makes for a fascinating double-team that in turn, retcons Negan's villainous past and explains the method to the madness of the bat-loving character. Earning 80% on Rotten Tomatoes and the green light for a 2nd season, you might even say he came out swinging for a second chance and it's something that his co-star has welcomed, even with their characters' testy dynamics. 

Speaking to Shondaland prior to the release of "Dead City," Cohan said, "Honestly, it's given us a chance to develop such a great friendship. Don't get me wrong — it's still hard for me because I love Jeff so much, but I love Maggie so much. So, it's a weird thing because I want to honor the story, but then I want to live my life and have fun with my partner in crime [laughs]."