10. Riddler

     The inquisitive Edward “E.” Nigma first presented himself as an adversary to the caped crusader in Detective Comics #140 in October of 1948. Posing as one of Batman’s oldest and outlandish villains in his rogues gallery, this mastermind trickster has given the dark knight a run for his money on more than one occasion. He earns his spot due to the notorious mental torment that he has given to Gotham City.

9. Scarecrow

     Dr. Jonathan Crane began his descent into madness by experimenting on the mentally deranged in the notorious Arkham Asylum. His obsession with fear and its neurological effects stems from childhood torment and fears, fitfully becoming “the Scarecrow”. His iconic mask and  fear toxin have been haunting Batman since his debut in Autumn 1941, in World’s Finest Comics #3.

8. Mr. Freeze

     Victor Fries commited the unthinkable in the vain of protecting and conserving his beloved, the terminally ill Nora. Originally called Mr. Zero when debuting in February of 1959, in Batman #121, Mr. Freeze is one the dark knight’s more tragic villains. Fries is willing to do anything to prolong the life of his dying wife, even if the casualties are inevitable. Batman struggles against this paradoxically cold and emotional technical genius, earning his spot among the best of Batman’s villains.

7. Two-Face

     Ally and close friend to both Bruce Wayne and Batman, Harvey Dent provides double the trouble against the caped crusader. With his first appearance in August of 1942, in Detective Comics #66, Two-Face decides the fate of those he ensnares in his criminal empire with the flip of a coin. With one of his most iconic stories being in Batman: The Long Halloween, the used-to-be white knight of Gotham has been developed incredibly throughout his villainous career. Posing a threat to not only Batman, but also Bruce Wayne, makes Two-Face a notorious adversary against the world’s greatest detective.

6. Hush

     Introduced as the childhood best friend of Bruce Wayne in January of 2003, in Batman #609, Thomas “Tommy” Elliot was obsessed with inheriting the family fortune, fatally so. After enduring abuse from his father, he rigged the family car to crash, aiming to kill his parents and indulge in the family fortune; however, this was thwarted by Thomas Wayne, who saved his mother, which fitfully ended the friendship between Bruce and Tommy. After time in a psychiatric ward and becoming a practiced surgeon, Elliot would later come back to Gotham to haunt Wayne under the alias of “Hush”. Hush can not only fight Batman physically, but also mentally, seeing as Tommy taught Bruce certain strategic efforts when they were young.

5. Catwoman

Selina Kyle has plagued Bruce Wayne’s heart since her debut in Batman #1, in Spring of 1940, dancing the line between good and evil. Her moments of genuine interest and love for Bruce Wayne are what make her a complicated and well-written rogue, making her emotional attacks all the more hurtful to the dark knight, but she has also proved to be a more than lethal physical adversary to Batman on more than one occasion.

4. Ra’s al Ghul

     “The Head of the Demon”, “The Man who Trained Batman”, Ra’s al Ghul has gone by many names over his hundreds of years of existence, being kept alive by the infamous Lazarus Pit. When Bruce Wayne was travelling the world to master the best detective and fighting techniques that mankind had to offer, Ra’s al Ghul was bound to arise, first appearing in Batman #232, back in June of 1971. Ra’s al Ghul not only taught Bruce Wayne everything he knows, but has witnessed years of conflict, mastering his own fighting strategies and leading the dark ninja clan, the League of Shadows.

3. Red Hood

     Batman has brought up several Robins over the years, and one of them was bound to turn on him. This is the case with the second Robin, Jason Todd, otherwise notoriously known as the Red Hood. After Dick Grayson, the first robin (who now works under the superhero title of Nightwing), left Batman to make a name of his own, Batman enlisted the help of a young boy who was stuck in the midst of Gotham’s underworld. Jason’s father was in jail, while his mother constantly battled drug addiction until her death, and Jason was left to fend for himself. Under the title of Robin, Jason was much more violent than his predecessor, which worried Bruce. After a series of feuds with his mentor, Jason, using the detective methods that he learned from Batman, found his mother alive and healthy. He quickly flew off to find her, later learning that it was trap set by the Joker, who later beat him to near-death and then leaving him next to a live bomb. Batman was too late to save Jason, but fate would no let Jason die just yet. Jason was resurrected by the Lazarus Pit, then trained by Ra’s al Ghul to use as a weapon against Batman. Jason undertook the mantle of the Red Hood, which was first used by the Joker in Detective Comics #168, as a mimicry of his killer and as a symbol of what he has become. The Red Hood operates under a simple could, the punishment must fit the crime.

2. Bane

     Born and trained in Santa Prisca Prison, Bane quickly became a ruthless fighter and genius tactician. Upon entering Gotham, Bane challenged the Batman and was determined to break him, to show him true fear. By carefully crafting a masterplan, Bane, with the help of Batman’s other rogues, was the first villain to truly break Batman after his appearance in Batman: The Vengeance Of Bane #1. Bane combines the brains and brawn, making him one of the greatest and most dangerous Batman villains around. If nothing else, Bane is the only villain to physically break the Bat.

1. Joker

Was there any doubt that Joker would be the best Batman villain on this list? First appearing in Batman #1, all the way back in April of 1940, he quickly became on of the most recognizable supervillains around. With a mysterious origin, and a knack to drive Batman insane, the Joker easily takes the top slot as the Dark Knight’s most difficult adversary. The Clown Prince of Crime is not only the best Batman villain but quite possibly the greatest comic book villain of all time.