The Man Who Laughs: The 20 Greatest Joker Moments, Part I

Arguably the most popular character in all of comic book lore is the Batman. For every great hero there needs to be a great villain, and for Bats, that is the Joker.

Originally created as a darker alternative to Superman, Batman’s popularity has actually come to surpass the Man of Steel over the last seven decades, and one of the biggest reasons why is the quality of villains he faces. None of those villains (or any villains anywhere) are more well-known than the Joker. He is the perfect foil for Batman. Chaos over order, insanity over logic, fear created through unpredictability rather than intimidation. Even the Joker’s vibrant purple suit clashes with Batman’s dark attire and seems to mock the Caped Crusader with its flamboyance. The sickest part of it all though,  is that without Batman, the Joker would cease to be. He is a character so ingrained in the rivalry, that Batman’s absence often increases Joker’s boredom, and he simply stops playing the game. It does give the Dark Knight’s quest a real sense of hopelessness when you consider he might do just as much good by simply hanging it up as it would likely mean his greatest foe would do the same.

With the newest incarnation of the Joker set to hit theaters in David Ayer’s Suicide Squad (or quite possibly even in Batman v Superman: Dawn of Justice), the Clown Prince of Crime is once again the talk of the town. So while we wait patiently to see the newest version of the Joker on the big screen, we thought we’d take a look at some of the most memorable and defining moments in the Joker’s history. Things that helped shape him and his relationship with the Bat, and led up to now.  We of course being myself, Brian Kronner, and fellow Batfan Scott Fraser.

#20. Christmas with the Dents

(The Long Halloween, 1997)

In the midst of one of the greatest stories ever told about Gotham City (The Long Halloween), Bats is trying to track down the serial killer known as ‘Holiday’ and thus not showering the Joker with the attention he craves. Becoming invested in stopping Holiday to regain the eye of his rival, Joker pays a visit to District Attorney Harvey Dent at his home. Dent is not only investigating the Holiday killings, but has also become a popular suspect, and the Joker wants to make sure to send a clear message; Gotham “isn’t big enough for two homicidal maniacs.” Joker leaves Harvey beaten and lying on the floor of his new home.

Christmas with the Joker

This sequence is important for a few reasons. First of all, this is before Dent became Two-Face, and at this time completed a trio with Gordon and Batman as the three men who would fix Gotham City. This makes an attack on him akin to Joker attacking Alfred Pennyworth at Wayne Manor, or the Gordons in their home. Of course Dent would go on to become Batman’s 2nd best villain (behind only the Clown) and much of his heroic lineage would be forgotten. At this time though, Harvey Dent was a crusader and the Joker recognized that. It also gives a real look inside why the Joker is so unpredictable. He doesn’t care about money or power, only the game he plays with Batman, and all of his moves are towards the goal of continuing the game.  

– B. Kronner

#19. Joker Kills Donna Gugina

(All-Star Batman & Robin #8, 2008)

All Star Batman & Robin was not something that was universally accepted by fans, many feeling that Frank Miller’s writing portrayed too dark a version of the famous crime fighter and that it was only Jim Lee’s art that fueled sales. Through the 10 issue run, Joker only appears in #8, and then only on a couple of pages despite being the subject of the book’s cover. What he does in his short appearance however proves to be substantial. Similar to early Harvey Dent, Donna Gugina is a lawyer in Gotham who is making a name for herself. As the issue opens, Donna and the Joker have just finished some adult activities at a seedy motel when the Joker informs her that important people will miss her, and proceeds to strangle her to death with his tie.

Joker and Donna

We never see his plan come to fruition concerning Donna because the series ended two issues later, but the brutal and emotionless way he carries out the act left a resounding impact on readers.  

– B. Kronner

#18. Joker Cuts Off His Face

(Detective Comics v2 #1, 2011)

When DC Comics decided to reboot every series they had and release 52 brand new #1’s, there was a bit of a question as to where that would leave some of our favorite heroes and villains. While some characters underwent serious changes to their histories, others made it through the reboot relatively untouched. The Batman line of characters is one of those that made it through with only a compressed timeline to worry about, so that should mean that the Joker’s story should be no different, right? Well, unfortunately, despite a huge buildup to the first issue of Detective Comics that featured Joker on the cover, fans were made to wait as the crazy clown made his first, and last, appearance in the New 52.


As Joker continues his murderous spree, he engages the Batman yet again in one of their ongoing feuds. After the battle he is sent away to Arkham Asylum, where the Dollmaker is waiting to perform a very special procedure. The Joker escapes Arkham, leaving behind his face pinned to the wall and disappearing from the New 52 for over a year. This moment not only left us wanting more of this ultra violent Joker, but let us know that while the rest of the DC Universe might be changing, the Joker was still the same sick, depraved, psychopathic clown he had always been. And in the year that he was missing, I think it’s safe to say no other character’s return to the New 52 was as highly anticipated as the Joker’s, and for good reason.

S. Fraser

#17. Removing the Red Hood

(The Killing Joke, 1988)

killing joke_reflection

This scene, which included perhaps the most iconic image of the Joker ever, is an important one. Alan Moore’s 1988 graphic novel The Killing Joke is the most accepted origin story we have. More than 25 years after it came out, it’s still looked upon as the closest we will ever get to seeing the Joker become who he is. A failed comedian with a murdered family, forced into criminal service. After being dropped into a vat of chemicals, he washes out with the waste and removes his Red Hood to reveal his reflection in the water, and he snaps.

Image (16) joker_killing-joke_480_1197656192_6.jpg for post 6262

This is the exact moment when the Joker becomes The Joker. A mental snap forced an already unstable individual past the breaking point and triggers a career of crime fueled by homicidal atrocities. This is where the Batman’s greatest adversary was born.

– B. Kronner

#16. Jack Nicholson’s Joker

(Batman, 1989)

There are more than a few great Joker moments from Tim Burton’s Batman, and rather than making multiple entries I figure it’s best to just cover them all at once. Jack Nicholson was the first actor to tackle the role of the Joker since the 1960s show that featured a mustachioed Cesar Romero in the role that helped define that era’s Joker. What Nicholson managed to do was bridge the gap between the campy clownster and the psychotic criminal that was currently being portrayed in the comics. His great performance as the Clown Prince of Crime gave the film a hint of disbelief while rooting it all in a realistic world, two opposing traits that combined to make a perfect setting for the Joker.


One of the key moments in Batman was of course the origin of the Joker, which was taken in part from an earlier entry on our list. The true transformation from Jack Napier to the Joker may have happened off-screen, but it was a key moment in the movie and gave us a fitting nemesis for Keaton’s Batman. Also telling the history of the character gave us a truly epic and memorable line delivered by a young Napier to an even younger Bruce Wayne;

Ever Dance with the Devil in the Pale Moonlight?

These are all great examples, however the shining moment for me stands out when Joker is staking his claim as the new leader of Gotham’s organized crime families.

The delivery of his lines, combined with the joy buzzer death of the opposition, set to the haunting laugh that Nicholson perfected for the role clearly make it one of the greatest Joker moments ever.

S. Fraser

That’s a pretty great start to our list of the Greatest Joker Moments Ever, and you just know they are going to keep getting better and better. We’ve really only scratched the surface, and have a ton of great moments left to cover, so I know you’ll be back next time as we continue our look at one of our favorite comic villains ever created.

Same bat-time. Same bat-channel.

(Sorry, we couldn’t resist.)


Images: DC Comics, Warner Bros.

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