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Mangaka Hideaki Sorachi as Hideaki Sorachi

Actor Minoru Shiraishi as Minoru Shiraishi

VA Sora Amamiya as Sora Amamiya

Ep5 21:00 - Sphere (left to right: Tomatsu Haruka, Kotobuki Minako, Takagaki Ayahi, Toyosaki Aki) appear onstage to perform the OP

Mangaka Ken Akamatsu as Ken Akamatsu

Director Shinichi Watanabe as Nabeshin (Also cameos as himself in numerous other series)

Mafia Kajita as Gurasan (a character who appears to be designed off himself)

Ep1 & 12 - Shouta Aoi as Shouta Aoi faces an epic encounter against T.M.Revolution in a live action Kamen Rider parody

Pro-golfer Momoko Oosato as Momoko Oosato

Ep1 7:40 - The Osomatsus meet their voice actors (Jun Fukuyama, Hiroshi Kamiya, Yuuichi Nakamura, Daisuke Ono, Takahiro Sakurai) at their graduation ceremony

EP38 - Former AKB48 member Mayu Watanabe, as undercover idol/witch Mayu Watanabe, hosts the Pumpkin Bird Festival

7:50 - Characters meet their VAs

VA Atsuko Enomoto cameos as herself

Vtuber Kizuna Ai as Kizuna Ai narrates the segment

Mangaka Masami Kurumada as Masami Kurumada

VA Hekiru Shiina as lovestruck supervillain Hekirunrun Shiina

Seikima-II band leader Demon Kogure as Demon Kogure

Idol group BiS members as themselves

Holostars as themselves

Miku's voice provider Saki Fujita as Miku Hatsune (This one's at the bottom since it's kind of cheating lol)

Anime based off Eriko Tamura who provides Eriko Tamura's singing roles (Also at the bottom since she doesn't actually voice her talking)

Mangaka Wayu Suzumiya as herself in the post-anime talk segment (Also kind of cheating but worth mentioning since the mangaka directs, voices and sings in their own adaptation)

Also off-theme but worth mentioning...
Features a chara, Makaino Kouji, designed off the composer of the same name who has written many theme songs for the series (though different VA)