Question: When did the character who was originally a villain but later became an antihero first appeared in a comic book?

full_context: Document 1: Richard Rory: Richard Rory is a fictional character in the Marvel Universe. He initially was a sort of author surrogate or alter ego for writer Steve Gerber, though Gerber is also shown to exist in the Marvel Universe. He was introduced in "Man-Thing" Volume 1, #2, a bit of a loner who rather easily befriended the nearly mindless monster. When in rural areas, he was frequently belittled for having a college education and a rather left-wing perspective. Later, under the pen of David Anthony Kraft, he became friends with She-Hulk, with slight romantic overtones that went nowhere. The character is named after Richard Cory, a nearly opposite character whose song was playing on the radio when Gerber created the character.
Document 2: Kingpin (character): The Kingpin (Wilson Fisk) is a fictional supervillain appearing in American comic books published by Marvel Comics. The character was created by Stan Lee and John Romita Sr., and first appeared in "The Amazing Spider-Man" #50 (cover dated July 1967).
Document 3: Gentleman (comics): The Gentleman (Gustav Fiers) is a fictional character, a supervillain and enemy of the Marvel Comics superhero called Spider-Man. The Gentleman is the brother of the Finisher, first appearing in a trilogy of "Spider-Man" novels written by Adam-Troy Castro before appearing within the comic books themselves. The Gentleman made his film debut in 2012 in "The Amazing Spider-Man", portrayed by actor Michael Massee.
Document 4: Flag-Smasher: The Flag-Smasher is the name used by two fictional supervillains appearing in American comic books published by Marvel Comics. The original was most often a foe of Captain America while other adversaries of the Flag-Smasher include The Punisher, Moon Knight, Ghost Rider, The Runaways, The Liberteens and Deadpool.
Document 5: Daredevil (season 1): The first season of the American web television series "Daredevil", which is based on the Marvel Comics character of the same name, follows the early days of Matt Murdock / Daredevil, a lawyer-by-day who fights crime at night, juxtaposed with the rise of crime lord Wilson Fisk. It is set in the Marvel Cinematic Universe (MCU), sharing continuity with the films and other television series of the franchise. The season was produced by Marvel Television in association with ABC Studios, DeKnight Prods. and Goddard Textiles, with Steven S. DeKnight serving as showrunner, and series creator Drew Goddard acting as consultant.
Document 6: Uncle Ben: Benjamin "Ben" Parker, usually called Uncle Ben, is a fictional character appearing in American comic books published by Marvel Comics, commonly in association with the superhero Spider-Man. Uncle Ben first appeared in "Amazing Fantasy" #15 (August 1962) and was created by writer Stan Lee and artist Steve Ditko. Modeled after American founding father Benjamin Franklin, the character plays an influential role in the Spider-Man comic books.
Document 7: Nick Fury: Colonel Nicholas Joseph Fury is a fictional character appearing in American comic books published by Marvel Comics. Created by writer/artist Jack Kirby and writer Stan Lee, Fury first appeared in "Sgt. Fury and his Howling Commandos" #1 (May 1963), a World War II combat series that portrayed the cigar-chomping Fury as leader of an elite U.S. Army unit. A popular character over a number of decades, in 2011, Fury was ranked 33rd in IGN's Top 100 Comic Book Heroes, and 32nd in their list of "The Top 50 Avengers". He has sometimes been considered an antihero.
Document 8: Richard Fisk: Richard Fisk is a fictional character, a criminal appearing in American comic books published by Marvel Comics. He is the son of the Kingpin and his wife Vanessa Fisk. Although he was originally a villain, he became an antihero.
Document 9: John Romita Sr.: John V. Romita Sr., often credited as simply John Romita ( ; born January 24, 1930), is an American comic-book artist best known for his work on Marvel Comics' "The Amazing Spider-Man" and for co-creating the character The Punisher. He was inducted into the Will Eisner Comic Book Hall of Fame in 2002.
Document 10: Rhino (comics): The Rhino is a fictional supervillain appearing in American comic books published by Marvel Comics. Although more than one character has assumed the identity of the Rhino, the first of these, and the one primarily associated with that identity, is Aleksei Sytsevich, who was created by writer Stan Lee and artist John Romita, Sr., and first appeared in "The Amazing Spider-Man" #41 (Oct. 1966).
Document 11: Punisher: The Punisher (Francis "Frank" Castle) is a fictional character appearing in American comic books published by Marvel Comics. The character was created by writer Gerry Conway and artists John Romita Sr. and Ross Andru, with publisher Stan Lee green-lighting the name. The Punisher made his first appearance in "The Amazing Spider-Man" #129 (cover-dated Feb. 1974).
Document 12: Ghost Rider: Ghost Rider is the name of many fictional supernatural antiheroes appearing in American comic books published by Marvel Comics. Marvel had previously used the name for a Western character whose name was later changed to Phantom Rider.
Document 13: Mary Jane Watson: Mary Jane "M.J." Watson is a fictional character appearing in American comic books published by Marvel Comics. Created by Stan Lee and John Romita, Sr., the character made her first appearance in "The Amazing Spider-Man" #25 (June 1965). She has been the best friend, main love interest and wife of Peter Parker, the alter ego of Spider-Man.
Document 14: Jack Murdock (comics): Jack Murdock is a fictional character appearing in American comic books published by Marvel Comics. He is the father of Matt Murdock known as the superhero Daredevil and the ex-husband of Maggie Murdock.
Document 15: Doctor Doom: Doctor Victor Von Doom (or simply Doctor Doom) is a fictional supervillain appearing in American comic books published by Marvel Comics. The son of Romani witch Cynthia Von Doom, Doctor Doom traditionally has been the archenemy of the Fantastic Four, and the leader of the fictional nation of Latveria. He is both a genius inventor and a sorcerer. While his chief opponents have been the Fantastic Four, he has also come into conflict with Iron Man, Spider-Man, Black Panther, the Avengers and multiple others. Doom has been depicted as a superhero, taking up the mantle of Iron Man from Tony Stark, and going on to join the Avengers.
ground_truth: July 1967