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

Context articles: Snapper Carr
Buddy Bradley
Comic Book Guy
Kingpin (character)
Doga (comics)
Nick Fury
Harley Quinn
Richard Fisk
The Rook (comics)
Spawn (comics)

Lucas "Snapper" Carr is a fictional character appearing in American comic books published by DC Comics.
 The character, whose fictional nickname is almost always used by other characters in favor of his given name, was created by Gardner Fox (writer) and Mike Sekowsky (penciller), and made his first appearance in "The Brave and the Bold" in February 1960.
 From 1960 to 1969, Snapper Carr appeared as a supporting character to the Justice League of America, a superhero team.
 The character occasionally appeared in comics featuring the Justice League from 1969 to 1989, when the "Invasion!
" limited-series comic book gave him superpowers.
 He was associated with a new superhero team, The Blasters, in various comics until 1993, when he lost his powers and became a main character in the "Hourman" comic book.
 After the cancellation of "Hourman" in April 2001, he became a main character in the "Young Justice" comic book beginning in December 2001.
 "Young Justice" was cancelled in May 2003, and he became associated with the governmental organization Checkmate, a role revealed when the character played a small but important role in the 2007-2008 limited series comic book "52 Aftermath: The Four Horsemen".
 The character made major appearances in "Final Crisis: Resist" in December 2008 and "Justice League of America 80-Page Giant" in November 2009.
Harold "Buddy" William Bradley Jr., generally referred to as Buddy Bradley, is a comic book character created by Peter Bagge and the main protagonist in several of his comic books, most notably "Hate" and "Neat Stuff".
 The character first appeared in Bagge's self-published "Comical Funnies" in 1981.
 In the 1990s Buddy became an iconic symbol of Seattle underground culture, with the character being associated with slackerdom and the grunge movement, something which his creator sees as fairly unintentional on his part.
 Bagge created Buddy as a fairly unlikeable character as a commentary on shallow hipster culture, but the character was immensely popular, with members of Generation X strongly identifying with Buddy and his problems.
 In this way he may have been seen as an antihero and archetype of 1990s underground culture.
 Bagge had the character enact storylines based on events from his past, such as his family life, adolescence and his move to Seattle in the 1980s.
Comic Book Guy is the common, popular name for Jeffrey "Jeff" Albertson, a recurring fictional character in the animated television series "The Simpsons".
 He is voiced by Hank Azaria and first appeared in the second-season episode "Three Men and a Comic Book", which originally aired on May 9, 1991.
 Comic Book Guy is the proprietor of a comic book store, The Android's Dungeon & Baseball Card Shop.
 He is based on "every comic book store guy in America" and represents a stereotypical middle-aged comic-book collector.
 He is well known for his distinctive accent, disagreeable personality and his catchphrase, "Worst [blank] ever!"
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).
Doga is a fictional character, an Indian comic book superhero character appearing in Raj Comics, published and distributed across India.
 Created by Tarun kumar Wahi, Sanjay Gupta & artist Manu in the November 1992, Doga is the first and as yet the only antihero character in Raj Comics.
 The character first appeared in the issue Curfew.
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.
Harley Quinn (Harleen Frances Quinzel) is a fictional supervillain and occasionally antihero appearing in American comic books published by DC Comics.
 The character was created by Paul Dini and Bruce Timm, and first appeared in "" in September 1992.
 She later appeared in DC Comics' Batman comic books, with the character's first comic book appearance in "The Batman Adventures" #12 (Sept. 1993).
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.
The Rook is a fictional, time-traveling comic book adventure hero created by Warren Publishing who first appeared in March 1977.
 He first appeared in Warren Publishing's "Eerie", "Vampirella" & "Warren Presents" magazines.
 In the 1980s, the Rook became popular and gained his own comic magazine title of the same name, "The Rook Magazine".
 In the 1990s, The Rook would be recreated in Harris Comics’ Chains of Chaos and The Rook comic book series.
 In 2014, The Rook was re-introduced in Dark Horse Comics’ Eerie Archives 17.
 The Rook returns with new adventures, written by Steven Grant and illustrated by Paul Gulacy in Dark Horse Presents and The Rook comic book series in 2015.
Spawn is a fictional character, an antihero that appears in a monthly comic book of the same name published by Image Comics.
 Created by Todd McFarlane, the character first appeared in "Spawn" #1 (May 1992).
 Spawn was ranked 60th on "Wizard" magazine's list of the Top 200 Comic Book Characters of All Time, 50th on "Empire" magazine's list of The 50 Greatest Comic Book Characters and 36th on IGN's 2011 Top 100 Comic Book Heroes.