Whether it be films or animated series, Batman's villains have often been memorable characters in their own right. Even in the comics, quintessential antagonists like the Joker, Poison Ivy, and Bane play a major part in revealing the dark knight's vulnerabilities and insecurities.
Whatever be their reason to wreak havoc in Gotham City, a large chunk of Batman's villains have had some great character development. On the other hand, there are a few other adversaries who haven't aged well or weren't developed enough as standalone characters. And then, there were a few villains who were caricature-ish enough by just their names.
BEST: The Joker
Without a doubt, the Joker would make an appearance in virtually any list that focuses on Batman villains. While analyzing him as a comic-book character, the most amusing element in his persona is his sheer unpredictability. While villains like Mister Freeze or Bane have ulterior motives behind their actions, the Joker often seems to engage in crime for the thrill of it.
And then, of course, the tension that he shares with Batman is what makes him inseparable from the DC hero. The Alan Moore classic The Killing Joke further gives readers a faint idea of his origin story as Red Hood, which contains a painful tale of tragedy and loss that eventually turns him into the homicidal maniac that he is today.
WORST: Kite-Man
Kite-Man's obsession with kites is hilarious and somewhat unique but he clearly doesn't fit in Batman's brooding real in comics. Maybe, he would have been good enough in the early days of Detective Comics. However, since Batman has had such diverse, scheming villains since the very beginning, Kite-Man's villainy falls flat.
He usually flies with a kite strapped to his back and, in situations of hand-to-hand combat, he relies on small kite-shaped blades. This absurd choice of weaponry might remind one of Penguin's reliance on lethal umbrellas. But in the case of Penguin, he has had such a well-developed backstory that even his goofiness might seem menacing.
BEST: Ra's Al Ghul
The so-called 'Head of the Demon,' Ra's al Ghul's ideology has often conflicted with that of Batman (even though both characters closely match each other's strategy and fighting skills). While he has appeared in multiple storylines, The Tower of Babel is a notable example as he discovers Batman's contingency plans to overpower his fellow Justice League members. It's a watershed moment in the JLA series as Batman is forced to confront his cynicism towards his own allies.
Leading the League of Assassins, he has also had familial relations with people who have been close to the Caped Crusader. He has, after all, been the father of Talia al Ghul and the maternal grandfather of Damian Wayne.
WORST: Penny Plunderer
In the year 1947, World's Finest Comics #30 introduced one of the strangest DC characters of all time. Joe Coyne aka Penny Plunderer was a newspaper-seller who stole pennies. When he's caught red-handed one day, Coyne gets so infuriated that he decides to lead a life of penny-stealing crimes.
In his debut, he used a giant penny as a deathtrap but Batman foiled his plans, keeping the penny for himself as a trophy. In fact, it's this penny that's more memorable than the villain because it's the same coin that Two-Face would later use to crush Batman. And now over the years, the coin has become a more identifiable symbol for Two-Face rather than the short-lived Penny Plunderer.
BEST: Poison Ivy
In theory, Poison Ivy's persona might not seem that terrorizing but the environmentalist/supervillain is easily one of Batman's strongest foes. Even though The New 52 and Rebirth storylines paint her as an anti-hero of sorts, Poison Ivy has had her moments to shine as a villain too.
Once a biochemist, Dr. Pamela Isley turned into Poison Ivy after a freak accident. Her alter ego allowed several of her ecological powers like poisonous touch, supernatural control over all sorts of plant life, and mind-controlling pheromones. Rather than causing unwanted collateral damage, she mostly targets the uber-rich capitalists for the sake of preserving the environment.
WORST: Mr. Camera
First introduced in Batman #81 (1954), Mr. Camera calls himself so because of an oversized camera that he wears as a helmet. He harbors an interest in committing crimes and taking snapshots from his camera-helmet. But Mr. Camera is so terrible at his villainous pursuits that he can't even click a decent photograph.
In one of his major comic appearances, he captures Batman and Robin without their masks, eventually blackmailing them. Finally, it's revealed in the third act that his photo of the Dynamic Duo was extremely blurry, not revealing any new information worth sharing.
BEST: Bane
Compared to the other villains, Bane is quite a recent adversary, having been introduced in Vengeance of Bane #1 in 1993. However, in the decades that followed, the ex-convict and genetically-altered assassin has garnered a cult fanbase.
Originally a prisoner in a South American island nation, Bane gained abnormal, physical strength as doctors forcefully experiment on him with the drug called Venom. His most important comic-book moment has to be his duel with Batman in Knightfall. From that moment onward, Bane gained the sobriquet of 'the man who broke the bat.' Despite breaking his back and forcing him to retire, Bane has been on Batman's side too while taking on druglords.
WORST: Ten-Eyed Man
Ten-Eyed Man is a bizarre entity in himself and his superpowers remain unclear. Once a Vietnam War veteran, he loses his sight after a warehouse explosion. For some unspecified reason, his doctor decides to connect his optic nerves to his fingers. So, technically, the 'power' that he possesses is that he can see from his eyes.
Killed off in Crisis on Infinite Earths, he's occasionally brought back in insignificant storylines. In the DC miniseries 52, he even creates a cult called the Ten-Eyed Brothers.
BEST: Harley Quinn
Created by Bruce Timm, Harley Quinn was initially an original character on Batman: The Animated Series. But her personality and her toxic romance with the Joker proved to be so iconic that she has become a popular Batman villain and anti-hero, spawning her own standalone comics too. The Batman Adventures: Mad Love touched upon her past life as a psychiatrist at Arkham Asylum. After falling in love with Joker, she gets manipulated by him to engage in his life of crime.
But over the years, Harley Quinn has drifted away from Joker's shadow and serves as a regular member on teams like the Suicide Squad and the trio Gotham City Sirens (in which she joined forces with Catwoman and Poison Ivy). She often relies on her gymnastic skills in combat and weaponized props to cause large-scale damage.
WORST: Calendar Man
Calendar Man was first introduced as a funny character, causing trouble on specific holidays and dressing up in flashy holiday-themed outfits. Over the years, he has acquired a more serious personality and is portrayed as a disturbed serial killer. But still, compared to the other villains in Gotham City, he hasn't created much of an impact, and his M.O of crimes isn't compelling enough.
In The Long Halloween, he appeared as a Hannibal Lecter-like maniac who knows about Holiday's whereabouts. However, he usually keeps this information from Batman, leaving little to no scope in building up any terror around his character.