In 1977, he graduated from Saitama Kasukabe technical high school. After graduating he attended a part-time design-related college but dropped out. In 1979, he joined an advertising company called POP Advertising. He made his debut as a cartoonist in 1987 when Weekly Manga Action began running his Darakuya Store Monogatari.
In August 1990, his series Crayon Shin-chan began running in Weekly Manga Action, the series started as a spin-off of the character Shinnosuke Nikaido (二階堂信之介) of Darakuya Store Monogatari. An animated series based on the comics began in 1992, and a Crayon Shin-chan boom followed the release of a 1993 animated film. For a year beginning in 1995, Usui's Super Shufu Tsukimi-San comic strip ran in the magazine Manga Life.
He and his wife raised two daughters; both had moved out of the house at the time of Usui's death.
Mt. Arafune, where Usui's body was found.
On September 12, 2009, Usui's family reported him missing from his hometown of Kasukabe when Usui did not return from hiking in nearby Gunma Prefecture. On September 19, 2009, a body with clothes matching those described in the report filed by Usui's family was found at the bottom of a cliff at Mount Arafune in Gunma. The body was identified by dental records and family members the next day as being that of Usui.
His camera was recovered and the final shot was taken from the cliff.
His funeral was held 23 September in a private service. It was attended by three thousand people.
Controversy arose when Chinese media showed the wrong picture of Yoshito Usui when reporting his death. The picture shown depicted Japanese artist Seitarō Kuroda [ja] (黒田征太郎), who was still alive. Seitarō Kuroda took a picture with Yoshito Usui once; this caused confusion, since there were not many pictures of Usui on the Internet.
1985 - Darakuya Store Monogatari (だらくやストア物語, Darakuya Sutoa Monogatari)