Batman The Killing Joke by Alan Moore, Brian Bolland, John Higgins (1988)

Source.

Proto Super Villians

Hop-Frog - Edgar Allan Poe (1850)
Hop-Frog - Edgar Allan Poe

The Black Coats (1863+)

Les habits noirs - Paul Féval (French only)

Dr. Nikola (1895-1901)
Dr. Nikola's Experiment by Guy Boothby
Dr Nikola Omnibus



Fantômas (1911)
Fantômas
Being the Second of the Series of the "Fantômas" Detective Tales
Messengers of Evil
Being a Further Account of the Lures and Devices of Fantômas

Fu Manchu (1913)
The Insidious Dr. Fu Manchu by Sax Rohmer
Clones
The Mysterious Wu Fang: The Case of the Suicide Tomb - Robert J. Hogan
The Sinister Dr Wong

Les Vampires (1916)

The Black Star (1916)
The Black Star

The Spider (1918)
The Spider Strain

Belphegor (1927)

The First Chapter (in English)
Belphégor the phantom of the Louvre (1965 Film Adaption)
Belphegor info and backgrounder at Cool French Comics

The Man Who Laughs (1928)

The Scarlet Slamander (1930)
The Scarlet Salamander

The Scarlet Ace (1932)
The Scarlet Ace

Doctor Satan (1933)
Mask of Death
Weird Tales/Volume 28/Issue 2

The Lightning (1938)

The Octopus (1939)
The City Condemned to Hell

The Scorpion (1939)
Satan's Incubator by Randolph Craig


Mesmerists

Svengali (1899)
Trilby by George Du Maurier

The Bat by Avery Hopwood and Mary Roberts Rinehart; Stephen Vincent Benet (1926)

Source.
c/f The Circular Staircase by Mary Roberts Rinehart

Some context.

From the Broadway production.

First film adaption.

(The 1930 sound film remake of this same film "The Bat Whispers" Bob Kane identified as partially inspiring Batman).

The Reign of Super Man

Interestingly, Jerry Siegel and Joe Shuster first conceived Superman as a bald telepathic villain bent on world domination. Kind of more like Lex Luther, in fact. Herbert Fine is the pen name chosen by the young collaborators. That provisional outing can be viewed here.