Question: Which super villain of Batman portrayed by Edward Nigma first appeared in the Detective Comics?

Context paragraphs:
Death of the Family: "Death of the Family" is a 23-issue comic book story arc first published by DC Comics in 2012 featuring the fictional superhero Batman and his family of supporting characters.  The arc spans several titles featuring characters of the Batman family including: "Batman", "Batgirl", "Batman and Robin", "Catwoman", "Detective Comics", "Nightwing", "Red Hood and the Outlaws", "Suicide Squad", and "Teen Titans".  The story involves the return of Batman's arch-enemy, the Joker, and his plan to destroy all of the people Batman has come to rely on over the years: the multiple Robins, Batgirl, Catwoman, Alfred Pennyworth, and Commissioner James Gordon.  The title is a reference to the classic Batman story arc "" (1988), in which the Joker murders Jason Todd.

Nightrunner (comics): Nightrunner is a fictional character created by David Hine and Kyle Higgins for publisher DC Comics.  A comic book superhero, Nightrunner first appeared in "Detective Comics Annual" #12 (February 2011).  Nightrunner is a 22-year-old French citizen of Algerian origin that lives in Clichy-sous-Bois in the eastern suburbs of Paris, France.  He was recruited by Bruce Wayne and Dick Grayson for Batman Incorporated as the Batman of Paris, "Le Batman Of France".

Batman (serial): Batman is a 1943 black-and-white 15-chapter theatrical serial from Columbia Pictures, produced by Rudolph C. Flothow, directed by Lambert Hillyer.  The serial is based on the DC Comics character Batman, who first appeared in "Detective Comics" #27 in May 1939.  It stars Lewis Wilson as Batman and Douglas Croft as his sidekick Robin.  The villain is an original character named Dr. Daka, a secret agent of the Japanese Imperial government, played by J. Carrol Naish.  Rounding out the cast are Shirley Patterson as Linda Page, Bruce Wayne's love interest, and William Austin as Alfred, the Wayne Manor butler.

Batman: Shadow of the Bat: Batman: Shadow of the Bat was a comic book series featuring Batman, published by DC Comics.  The series ran for 96 issues, from 1992 to 2000.  The stories took place in Batman's then-current continuity along with "Detective Comics" and "Batman", in contrast to "", which focused on Batman's early years.  "Shadow of the Bat" looked into the psyche of the various cast members of the "Batman" comics.

The Batman: The Batman is an animated television series produced by Warner Bros.  Animation and based on the DC Comics superhero Batman.  It ran from September 11, 2004 to March 8, 2008, on the Saturday morning television block Kids' WB.  Although the series borrows many elements from previous Batman storylines, it does not follow the continuity set by the comic books, the film series, nor that of "" and its spin-offs.  The character designs were provided by "Jackie Chan Adventures" artist Jeff Matsuda (who also directed the ending), with the appearances of many of the supervillains, like the Joker, Penguin and Riddler, being radically altered from those of their comic counterparts.

The Batman Chronicles (trade paperback): The Batman Chronicles is a series of trade paperbacks published by DC Comics, intended to reprint all Batman stories from "Detective Comics", "Batman", "World's Finest Comics", and other titles throughout the character's history, chronologically (based on publication date), starting with his earliest appearances.  Whether or not the series will collect the post-Crisis version of Batman as well remains to be seen.  They are priced significantly lower than the "Batman Archives" series in order to be more affordable for the reader.  Each volume is typically priced at $14.99 USD.  11 volumes have been produced so far.  After a 2-year hiatus, "The Batman Chronicles" returned with volume 11 in December 2012.  No further volumes have been announced yet.

Jason Bard: Jason Bard is a fictional character in the DC Universe.  He first appeared in "Detective Comics" #392, which was published in 1969.  He appeared in several back-up stories throughout the 1970s and 1980s in "Detective Comics".

Two-Face: Two-Face (Harvey Dent) is a fictional supervillain appearing in American comic books published by DC Comics, commonly as an adversary of the superhero Batman.  The character was created by Bill Finger and Bob Kane and first appeared in "Detective Comics" #66 (Aug. 1942).  As one of Batman's most enduring enemies, Two-Face belongs to the collective of adversaries that make up Batman's rogues gallery.

Batman (comic book): Batman is an ongoing American comic book series featuring the DC Comics superhero, Batman, as the main protagonist.  The character first appeared in "Detective Comics" #27 (cover dated May 1939).  Batman proved to be so popular that a self-titled ongoing comic book series began publication with a cover date of Spring 1940.  It was first advertised in early April 1940, one month after the first appearance of his new sidekick, Robin, the Boy Wonder.

Riddler: The Riddler (Edward Nigma) is a fictional supervillain appearing in American comic books published by DC Comics, commonly as an adversary of the superhero Batman.  The character made his first appearance in "Detective Comics" #140 (October, 1948) and was created by Bill Finger and Dick Sprang.

Supporting paragraphs: The Batman Riddler
Answer: Riddler