Very soon after the new style of humorous drawings, the cartoon, emerged in the 19th century, artists began to draw spanking cartoons. These were either illustrations for stories, poems, or newspaper articles, or were "standalone" humorous cartoons with just a short line of text, or no words at all.
 Vintage spanking cartoons
These cartoons presented the subject of spanking for the first time from a whole variety of new perspectives. What used to be a serious, grave matter - the subject of punishment - was now reflected with new eyes that saw the richness of its many facettes, from the humorous to the pathetic, from the cruel to the romantic, from the contradictory to the absurd. Spanking proved a subject ideal for the cartoon. The audience loved it because everyone would immediately sympathize with the poor chap suffering the painful and embarassing chastisement.
Many 19th century spanking cartoons were drawn by artists such as Wilhelm Busch, the "grandfather of the comic". In the beginning of the 20th century spanking postcards became very popular. These were postcards that featured a humorous spanking cartoon, usually accompanied with a short line of text which was often a pun or other play with words.
When the first comics in the modern sense of the word came up in the early 20th century, a lot of them made use of the great popularity of the spanking theme. For more on the "golden age of spanking in comics", see spanking in comics.
Humorous cartoons that mostly depicted husband-spanks-wife scenarios, were popular from the 1930s to the 1960s in a wide variety of mainstream magazines, journals of humor, and racy men's magazines. An extensive database of this art is archived at the Chicago Spanking Review website.
 Political spanking cartoons
- Main article: Spanking in political satire
Spanking cartoons are also often encountered in political satire. Here, the spanking is generally meant metaphorically, with the spanker and spankee representing e.g. politicians or nations.
 Humor magazines
In the 1950s and '60s there were dozens of mildly risque mainstream humor magazines that frequently featured spanking cartoons. Sometimes spanking art appeared on the front cover. The pairings were almost always M/F, with various male authority figures (husbands, bosses, doctors, and policemen) giving wives, secretaries, female patients and law-breakers a humiliating dose of over-the-knee discipline. The tone of these cartoons remained mocking and lighthearted. Some had a faint hint of implied eroticism, but no nudity was ever shown.
There was also the occasional spanking parody. The sexy Daisy-Mae character from the popular newspaper comic strip Li'l Abner is seen getting spanked on the cover of Joker (August 1956) and in the July 1961 issue of Romp.
The September 1956 issue of Jest featured a spanking art cover by Bill Ward. (Ward did dozens of these drawings for a variety of publications.) Jest printed similar cartoons in July 1957, July 1959, and May 1960.
Just a few of the countless magazines with humorous corporal punishment cartoons include Gee-Whiz (September 1956), Gaze (February 1957), Comedy Riot (May 1957), Comedy (March 1958), Breezy (April 1959), Cartoon Parade (November 1962), Laugh Riot (August 1965), Zip (November 1966), Fun House Comedy (July 1966), Joker (January 1967 & August 1970), and Popular Jokes (November 1968).
 The 1960s -1970s
In the 1960s and 1970s the practice of spanking children became increasingly frowned upon, and this effectively put an end to the popularity of spanking cartoons in general which were now considered politically incorrect, cruel, and "not funny" anymore.
However, humorous cartoons of women being spanked (and sometimes flogged) continued in various men's magazines such as Playboy, Penthouse, and Britain's Mayfair.
Below are some examples:
- Playboy (July 1965): Three men out for a night of bowling are turned away at the door of a friend by his girlfriend who is wearing a black corset and holding a martinet whip. Caption: "He can't go out tonight—he's being punished."
- Playboy (November 1965): A man catches his wife in bed with another man. Naked, she is over his knee as he raises his hand. Caption: "Repeat after me: 'I will not commit adultery again'!"
- Playboy (April 1969): In the recurring comic "Little Annie Fanny", Annie is seen covered with whip lash marks from shoulder to thigh from filming a "love scene" in a sexploitation film.
- Playboy (November 1969): A man holding a long, multi-tailed whip approaches a prostitute. The madam tells her: "Come now, Glenda, there's a first time for everything."
- Playboy (September 1970): A biker type flogs his girlfriend who is on the floor, her wrists tied to a door knob. She says: "But will you still love me after the novelty wears off?"
- Playboy (January 1972): A client holding a cane approaches a prostitute as the madam says to her: "It's Mr. Cosgrove to wish you the compliments of the season, my dear."
- Playboy (June 1972): Little Annie Fanny gets an over the knee hand spanking (see picture)
- Playboy (October 1972): While his nude wife hangs upside down from a light fixture in the next room, a naked man holding a flogger talks on the phone: Caption: "Just taking a few home movies with the wife. What are you doing?"
- Mayfair (November 1972): A M/F caning in a British school setting from the strip Carrie (see picture).
- Penthouse (1973-1980): the comic strip serial "Oh Wicked Wanda" had numerous F/F and M/F spanking and flogging scenes. (See images.)
 Modern spanking cartoons
The 1990s brought a renewal of the spanking cartoon with the emerge of the first spanking art Internet fan communities. Among the fans were some who used their creative potential, became hobby spanking artists and shared their artworks for free with other fans.
Also, some of the vintage cartoons from the early 20th century, which were now in the public domain and could therefore be reproduced without copyright infringment, became popular again. Some of the spanking postcards were reprinted. Other vintage cartoons were scanned by their owners and shared with other fans digitally via the Internet.