Osomatsu-kun is a manga series by Fujio Akatsuka which ran in Shōnen Sunday from 1962 to 1969. It has been adapted into two different anime series of the same name, the first in 1966, produced by Studio Zero, and the second in 1988, produced by Pierrot and aired across Japan on Fuji Television and the anime satellite television network, Animax.

This series helped establish Akatsuka's reputation as a gag comic artist, long before his other popular manga, Tensai Bakabon. Osomatsu-kun has appeared in numerous special issues of Shōnen Sunday. Akatsuka has also included several manga adaptations of routines from Charlie Chaplin movies in the series.

Won the 10th Shogakukan Manga Award in 1964.

(Source: Wikipedia)

A series of short episodic stories revolving around a mischievous girl named "Jajako". Every strip features her in some sort of strange or silly situation, usually causing trouble for various adults in her life, one often being her mother.

(Source: Mangadex)

Eccentric young man "Santarou" is constantly in search of love, most of the time, from the often calm and collected "Chiyoko". Hijinks ensue as in every chapter he devises a new scheme or gimmick to gain the affection of Chiyoko or other girls. However, with the help of his opportunistic little sister "Nanako", things often get out of hand. There is little continuity within each chapter, instead opting for interesting episodic stories.

(Source: Mangadex)

Matsuno household has six naughty and mischievous sons (who are sextuplets), led by the eldest Osomatsu. They were grade schoolers back in the Showa period, but despite of still living in the same old household, the street view as well as the life style of modern day society have changed drastically.

(Source: ANN)