Making his debut in the very first Batman comic book, the rivalry between the Joker and the Dark Knight spans more than 75 years and, as you can imagine, there have been quite a few memorable stories written over that time. But with such a rich history to choose from and so many different artists interpretations of the character, how can someone who’s just getting into comics ever hope to hone in on the defining story arcs that have given rise to one of the greatest (if not the greatest) villains of all time? That’s where we come in. Collected here are 13 of the most momentous and highly acclaimed stories featuring the Clown Prince of Crime. So read on and maybe you’ll get a feel for which take on the Joker you think should be considered the definitive version.

13. The Joker’s Five-Way Revenge (Batman #251, 1973)

After the ’60s Batman TV series ended its run, both the Dark Knight and the Joker’s reputation were in serious need of repair to help remind audiences that they weren’t all about simplistic youth-aimed moral lessons like eating your vegetables and doing your homework. In this story featured in Batman #251 (1973), Denny O’Neil and Neal Adams deliberately tried to avoid the campy antics that had become synonymous with the Joker since the debut of the Adam West TV show.

The story centers around the Joker taking violent and twisted revenge on five former gang members that betrayed him, prompting Batman to take action to protect a group of people he would normally be trying to put behind bars. From the opening page it re-establishes the Joker as an unsettling and murderous psychopath who has a blatant disregard for the lives of others—including his own allies. It was also seminal because it established a trend whereby the Joker appeared far less frequently in comics, thus making his character far more impactful. The conclusion of the story also holds a lot of weight because it showed the Joker actually getting the best of Batman in battle; however, since he was well aware that the Dark Knight was in a severely weakened state, he refused to deliver the killing blow—demonstrating one of the first instances that the two characters’ existences are dependent on one another.

12. The Laughing Fish  (Detective Comics #475, 1978)

This was another story that did a lot to restore gravitas to the Joker’s character. By blending classical Joker elements (such as his trademark grin, and a scheme involving poisoned fish) with his modern portrayal as a deranged sociopath, Steve Englehart and Marshall Rogers perfectly capture the Joker’s insane sense of humor as he hatches his plan to poison Gotham City’s fish supply with Joker toxin.

Rogers was also one of the first artists to de-accentuate the look of the Joker’s chin, which resulted in a much more realistic look for the villain.

11. Soft Targets (Gotham Central #12-15, 2003)

This one’s a bit of an odd entry considering it barely even features the Joker in the flesh. For most of the story, the Joker is an aggravating off-page presence who cunningly picks off Gotham’s public figures and throws the city into a state of panic. Artist Michael Lark’s take on the Joker bears an uncanny resemblance to Jack Nicholson’s movie version, with many of his expressions and mannerisms looking as if they were taken right off the silver screen. The story is also notable for containing a scene where the Joker beats a guy to death with a phone book.

10. Slayride (Detective Comics #826, 2007)

A standalone holiday-themed comic from Batman: The Animated Series co-creator Paul Dini, this story sees the third Robin, Tim Drake, kidnapped by the Joker in an SUV and forced to watch as he runs over as many people as possible. Dini’s Joker gives us some of the best dark comedy we’ve ever seen from the character, as he does things like call 911 to report a hit-and-run just before mowing down a pedestrian, or when he shoots a drive-thru operator for messing up his order. If you’re looking for a fun read that still delivers on the violence, this is probably the most delightfully psychotic depiction of the Joker you’ll ever find.

9. Arkham Asylum (Original Graphic Novel, 1989)

Featuring the wickedness of Frank Miller’s Joker, the sick humor of Steve Englehart’s Joker, and the mischievous drive of the original Joker, Grant Morrison’s interpretation of the Clown Prince of Crime in Arkham Asylum is a fantastic amalgamation of all the previous representations. While the story presented isn’t quite as good as it is in a lot of the other entries on this list, the Joker is positively captivating. His intimidating psychosis and perverse sense of humor are on full display when he does things like pretend to have stabbed a hostage’s eyes out with a pencil only to have her later emerge unscathed as part of twisted reverse April Fools’ prank.

And, of course, we can’t forget to mention the work of Dave McKean, whose stunning Joker illustrations are, to put it mildly, nothing short of an acid nightmare.

8. Mad Love (Batman Adventures One-Shot, 1994)

Set following the events of the acclaimed ’90s Batman animated series, Mad Love explores Harley Quinn’s origins from her beginnings as Harleen Quinzel, a young and impressionable psychiatrist at Arkham Asylum who took the Joker on as her patient. The story really showcases the Joker’s manipulative side superbly and adds a modicum of compassion to his character as we see Harley go from being a lowly female goon to his favored sidekick and eventual lover. Mad Love gives the Joker a level of emotional depth that few other stories have managed to convey, an accomplishment that probably contributed to it winning an Eisner Award for “Best Single Story” in 1994.

7. A Death in the Family (Batman #426-428, 1988-89)

In one of the most savage storylines ever, A Death in the Family saw the Joker escape Arkham Asylum and go on a rampage of destruction that brought him into contact with the second Robin, Jason Todd. After taking a crowbar to Todd as if he were a candy-filled pinata, the Joker leaves a bomb behind that would have killed The Second Boy Wonder’s mother had Todd not used his own body to smother the explosion—saving her life and ending his in the process.

The story concludes with the Joker somehow managing to finagle diplomatic immunity by becoming the Iranian ambassador, a strange and somewhat racist twist despite the fact that this was before the DC universe introduced the fictional Middle Eastern nation of Qurac to suit all of its conventional terrorist needs. But regardless, this is still a landmark Joker story, and one that garnered him a lot of favoritism by all those readers who thought Jason Todd was nothing more than a whiny little b–tch.

6. The Joker (Batman #1, 1940)

Believe it or not, the Joker was initially intended as a one-off character who was supposed to die at the end of the very first issue of Batman. However, the purple-suited villain created by Bill Finger, Bob Kane and Jerry Robinson turned out to be such a remarkable creation that the publishers ultimately felt they should keep him around for future confrontations with the Caped Crusader.

When the Joker made his debut he wasn’t quite the theatrical showboater that a lot his later iterations made him out to be, although he did prove to be an expert of media manipulation right off the bat, announcing his first malicious crimes through public radio.

Bob Kane’s dark and doleful artwork perfectly suits the tone of the story, and the Joker’s gangster-clown look Kane and Robinson came up with gave off a creepily menacing vibe that future artists seemed to enjoy taking to the extreme in subsequent appearances.

It’s especially fun to go back and read this story knowing the Joker was supposed to die at the end. To think that one of the greatest villains ever created almost met his end by accidentally stabbing himself in the heart during a fight with Batman. Thankfully, an editor with the gift of foresight commissioned a last-minute panel that showed the Joker still alive in an ambulance. Considering how integral the character has become in shaping Batman’s identity, you have to wonder how the Dark Knight might have turned out if the Joker was never seen again after that first issue.

5. The Man Who Laughs (Original Graphic Novel, 2005)

The Man Who Laughs is based on the Joker’s first appearance in Batman #1 and serves as a somewhat sequel to 1987’s Batman: Year One. It tells the story of Batman’s first encounter with the Joker in the post-crisis continuity, and the story has since come to define the Joker for modern day audiences by retelling the supposed origin of how his body and mind were mangled at the Ace Chemical Plant.

This comic makes use of a lot of the elements various writers have added to the Joker’s character over the years to convey a more complete and integrated version of the character than any previous origin story has been able to deliver. But make no mistake, this Joker is still as sinister as ever, proven by the senseless slaughter of innocent victims which he carries out for seemingly no other reason than the sheer joy he derives from it.

Fun fact—the title of this story is a direct reference to the 1928 silent film The Man Who Laughs (based on the Victor Hugo novel) which featured Conrad Veidt in a role that became the inspiration for the original Joker.

4. Going Sane (Legends of the Dark Knight #65-68, 1994-95)

An interesting story that never seems to get the attention it should, this four-issue fable by J.M. deMatteis sees the Joker finally achieve his ultimate goal by killing Batman. An action that results in him letting go of the Joker persona and become a seemingly normal person.

Seeking to bury his sadistic side, the Joker undergoes plastic surgery and takes on what could pass as a likeable personality going by the name of Joseph Kerr (get it?). But, of course, as it would happen, Batman was never really dead, and his existence stirs up some latent memories in old Joe Kerr that bring him back to his old habits of hostage taking and rigging things with explosives.

In all honesty, not everything in the story works flawlessly, but no other story better highlights the importance of Batman to the Joker by showing that he isn’t merely the curse of the Joker’s criminal existence; he is, in fact, an integral part of what makes the Joker the Joker.

3. Joker (Original Graphic Novel, 2008)

Released around the same time Christopher Nolan’s definitive Batman movie, The Dark Knight, there remains some confusion about whether Heath Ledger’s brilliant portray of the Joker was inspired by this graphic novel or vice versa.

Brian Azzarello’s version of the Joker is an insane criminal who’s the product of rampant drug abuse—drinking, popping pills and snorting cocaine that send him into a crazed blood-thirsty rampage. The Joker in this book is more realistic and more disturbing than many other iterations, as Azzarello takes full advantage of the comic medium to have Joker perform atrocious acts of violence like breaking into a random apartment and mutilating an elderly couple for fun.

The story is told from the perspective of Joker’s hired goon and chauffeur Johnny Frost, who witnesses his return to the Gotham and the rebuilding of his lost empire. Through Joker’s interactions with Johnny, Azzarello does an excellent job of contrasting the charismatic nature of his personality character with his horrifying sadistic temperament. In one panel the Joker will seem somber and almost likeable, and the next panel you find out that he raped Johnny’s wife just to test his loyalty.

Joker is a very dark and compelling story that will make you question any sympathy you ever had for the Clown Prince of Crime.

2. Death of the Family (23-Issue Arc Spanning Nine DC Titles, 2012)

Not to be confused with A Death in the Family, Death of the Family was the first major storyline for the Joker in the current New 52 continuity. After surgically removing his face and escaping Arkham Asylum, the Joker reappears in Gotham and announces that he knows the secret identities of every member of the Bat-Family (not including Batman), and that he would be systematically killing them off one by one so that things could be like there were in the old days with just him and Batman.

The story, written by Scott Snyder, revisits all the significant locations that hold meaning for Batman and Joker, such as ACE Chemicals, Arkham Asylum, and the Gotham Reservoir (complete with toxic Jokerfish). Snyder does a great job of fleshing out the relationship between Batman and Joker with Joker, atone point, declaring his love of the Dark Knight and framing their relationship as some sort of twisted bromance with Batman acting as a Dark King and the Joker his trusted Jester-advisor. Batman even questions his infallible moral code and wonders if killing Joker would be the best course of action given the villain’s inability to be reformed and his penchant for escaping Arkham. Death of the Family is a modern masterpiece providing an intense and gripping story that really gets to the heart of what makes the Joker tick.

1. The Killing Joke (Original Graphic Novel, 1988)

Widely considered to be the definitive portrayal of the Clown Prince of Crime, The Killing Joke was Alan Moore’s 1988 masterwork that saw the iconic villain in his most cold-blooded and sadistic form. Moore also provided another possible origin story for the character, portraying him in the past as a family man and struggling comedian who, after resorting to criminal activity to solve his financial problems, is thwarted by Batman before being disfigured, driven insane and transformed into the Joker.

The graphic novel blends two storylines together with the Joker’s origins as Jack, running parallel to a present day story where the Joker shoots and paralyzes Barbara Gordon and then kidnaps her father Jim to make him watch her naked and helpless from the confines of a circus cage. His endgame in this scenario was to push Jim Gordon over the edge and prove that even the most sane man can go crazy with the right prodding.

Though it has always been a cardinal rule among Batman writers to never reveal the Joker’s true origins, since the story is being told by the Joker himself, it could easily be interpreted as just another tall tale from a proven pathological liar.

The story also features a very controversial ending in which Batman and Joker stand face-to-face in the abandoned amusement park laughing at a joke. Then, on the final page, Batman reaches over towards the Joker, the laughter fades, and the lights go out. Did Batman kill Joker? The title of the comic might suggest that he did, but readers will probably never reach a consensus.