At age 14, Kotondo agreed to leave school and begin studies with Kobori Tomone, a yamato-e painter. Along with painting classes, Tomone taught Kotondo about the court and military practices of ancient Japan, satisfying his interest in history. A year later, he was officially adopted as the next heir of the Torii school and assumed the artist's name 'Kotondo'. While still studying with Tomone, he began designing illustrations for a theatrical magazine, Engei Gaho ('Entertainment Illustrated Magazine'), and painted kabuki posters and billboards.
In 1917, Tomone recommended that Kotondo begin studies with Kaburagi Kiyokata, the famous painter. Kiyokata was a master of bijin-ga paintings and prints, and he had a thorough knowledge of the kabuki theater, something which would be important for the future Torii master. Soon afterwards, Kotondo began studying in Kiyokata's painting school and came into contact with such notable students as Kawase Hasui and Ito Shinsui. Kotondo's bijin-ga style was certainly influenced by both Kiyokata and Shinsui, and perhaps also by the shin hanga artist Hashiguchi Goyo.
During the following years, Kotondo produced numerous bijin-ga paintings with a luminous softness about them. He used the pseudonym 'Masahiko' to sign these paintings, a name derived from masa, a character in one of his father's pseudonyms, and hiko, a character used by many of Tomone's students to show respect for their teacher. After the Showa era commenced in 1926, he began using the name 'Kotondo' to sign his paintings. Kotondo officially assumed the leadership of the Torii school in 1929, the year his father retired.
Kotondo's first woodblock print, Applying Powder, was published in 1929 by Kawaguchi and Sakai. Unlike the other print designers of his time, he never worked with the publisher Watanabe Shozaburo. Kotondo designed twenty-two bijin-ga prints, some of which were printed with several color variations. At first he worked with the publishing partners, Kawaguchi and Sakai. After they dissolved their partnership, Kotondo worked with Kawaguchi. In the 1930's, he worked with the publisher Ikeda. Many of his prints were carved by the master, Maeda Kentaro, and printed by Komatsu Wasakichi. Kotondo's last bijin-ga print was published in 1934.
In 1937, Kotondo began to pursue his kabuki roots, and became an art director for the Imperial Theater and for Japanese kabuki cinema. He decided to again change his artist name, this time to 'Kiyonobu'. It was tradition for Torii masters to use the kiyo character in their name. The nobu character was chosen to honor Torii Kiyonobu, the first master of the Torii school. It was slightly different from the character used by the first Torii, in order to show deference and respect. Perhaps these frequent name changes helped Kotondo to proclaim his changing style. Some people did not even realize that Masahiko, Kotondo, Kiyonobu, and later Kiyotada were all the same artist.
Kotondo's father, Torii Kiyotada VII, died in 1941 and he officially became Torii VIII. After World War II, Kotondo worked with the Meiji-za Theater and the Kabuki-za Theater. He was also an art consultant for television programs. Kotondo continued to create kabuki paintings and bijin-ga paintings, very different from his earlier works under Kiyokata. Kotondo took the name 'Kiyotada' in 1954 to honor his father. In the same year, he had a one-man show of theatrical paintings at the Shibuya-Toyoko Department Store in Tokyo, probably to introduce the new style of the Torii school.
During the later years of his life, from 1966 to 1972, Kotondo taught a theatrical art class at Nihon University. He planned to write a detailed book on the traditions of kabuki costume and stage designs, but did not have the time to do the research necessary for such a large project. He also had plans to produce other bijin-ga prints in the Kiyotada style, a different style than his earlier shin hanga prints. Unfortunately, none of this came to fruition. But what Kotondo did leave this world is very impressive indeed. He not only created a wealth of extraordinary prints and paintings, but also passed down his knowledge and teachings to his daughter, Torii Kiyomitsu. She became the ninth (and first female) master of the Torii school in 1982.