Being poor at the time, he “could not shut [his] eyes to the poverty around [him] and engage in the pursuit of pure artistic ideals.”[10] Akasegawa also reported his frustration with the socialist realism aesthetic that predominated at the Nihon Indépendant during these years,[10] wanting something which “linked real life and painting as closely as possible.”[10] In the late 1950s, Akasegawa began submitting works to the more freewheeling and less ideological Yomiuri Indépendant Exhibition.

[11] He has recalled that toward the end of the 1950s a competition emerged among artists showing at the Yomiuri Indépendant to see whose painting could extend furthest from its surface.

[11] This year proved a turning point for the artist as it gave rise to both the massive Anpo protests and the founding of the Neo-Dada Organizers.

[13] The members included, along with Akasegawa, artists acquainted through the Yomiuri Indépendant such as Ushio Shinohara, Shō Kazakura, Kinpei Masuzawa, and Shūsaku Arakawa.

[14] Other artist frequently involved though not officially a part of the group included Tetsumi Kudō, Tomio Miki, and Natsuyuki Nakanishi, with whom Akasegawa would later go on to form Hi-Red Center.

[18] In this group performance, which included prosthetic male genitalia, a fake wound reminiscent of seppuku rituals, and other disturbing imagery, Akasegawa appeared in a head-wrap and a “grotesque, monster-like costume and took massive gulps directly from a bottle of strong shōchū alcohol while dancing around bizarrely and making awful noises.”[18] Anpo Commemoration Event demonstrated the overlapping concerns of the Anpo protests and the Neo-Dada Organizers, both manifestations of social discontent with the existing institutions of Japan in 1960.

The group's name was formed from the first kanji characters of the three artists' surnames: "high" (the "Taka" in Takamatsu), "red" (the "Aka" in Akasegawa), and "center" (the "Naka" in Nakanishi).

[24] For this exhibition, Akasegawa presented a chair, electric fan, radio and carpet, items symbolic of Japan's growth as a modern, capitalist society, all wrapped in brown paper.

[2] All three artists had begun as painters but had turned to methods of “direct action” through Hi-Red Center, a term taken from prewar socialist agitators.

[7] Participants included Yoko Ono and Nam June Paik, and were photographed from six sides to create a quasi-medical document ostensibly meant for the outfitting of personal fallout shelters.

[31] Members of the Tokyo art community as well as others, including Jasper Johns, attended this opening event in which the gallery was revealed to be full of empty cans.

[32][7] Of these works, some cans were soldered shut and at other times their lids were left ajar, revealing the label lining the inner wall.

[38] Akasegawa's note was first discovered by the Japanese authorities during a raid on the houses of members of the radical leftist group Hanzaisha Domei (League of Criminals).

[35] The police were investigating an allegedly pornographic photograph in a book titled Akai Fusen Aruiwa Mesuokami No Yoru (Red Balloon, or Night of the She-Wolf).

[35] However, because Hanzaisha Domei was monitored by the authorities as “ideologically perverse” (shisoteki henshitsu-sha), members of the group were arrested and the news was publicized in major newspapers and weekly magazines.

[39] He developed this theory of “modeling” in response to the concept of counterfeiting as defined by Japanese law immediately after he gave depositions to the Tokyo Metropolitan Police in January 1964.

[38] Akasegawa recorded his thoughts and experiences as the trials were proceeding in a series of essays published in 1970 in the collection titled Obuje o motta musansha (The Proletarian Carrying an Objet).

"[49] These activities arose from jokingly likening odd urban phenomena to conceptual art gestures, such as stairs leading to an entrance that had since been removed.

In January 1986, Akasegawa and his collaborators, Terunobu Fujimori, Shinbo Minami, Tetsuo Matsuda, Tsutomu Ichiki, and Joni Hayashi, met with Geijutsu Shincho editor Takeshita Tachibana to announce the formation of a new group: Rojō Kansatsu Gakkai (Street Observation Society), abbreviated as Rojō.

Akasegawa was fond of old cameras, especially Leicas, and from 1992 to around 2009, he joined Yutaka Takanashi and Yūtokutaishi Akiyama in the photographers' group Raika Dōmei, which held numerous exhibitions.