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The gangsters are two trios of minor villains from Higurashi no Naku Koro ni Kira, the light-hearted and comedic OAV fourth season of Higurashi no Naku Koro ni. They appear in Musubienishi-hen.

The first trio of gangsters was seen hanging out at Angel Mort where Keiichi Maebara had been invited to its dessert feast by Shion Sonozaki, who had disguised herself as Mion during her inviting of him earlier. The gangsters fell in love with Shion, whom they thought was Mion and tried to steal her, but Keiichi saved her and stood up to them, scaring them into running away from Angel Mort as fast as they could.

Later, another trio of gangsters, this time bikers, also met Keiichi and Shion at a sidewalk. The bikers also fell in love with Shion and tried to steal her as well, but Keiichi was quick to get in their way and stand up to them as well to protect her, which reminded Shion of Satoshi Hojo protecting her. The bikers managed to knock Keiichi down however, and were about to steal Shion, but luckily, her bodyguard, Kasai Tatsuyoshi, came along and gave the bikers an angry look in his eyes. Kasai's angry look scared the bikers and chased them away as well.

The bikers previously appeared in Higurashi Kai's Minagoroshi-hen, where they assaulted Rika only to be stopped by Kasai.

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           When They Cry Villains

Higurashi: When They Cry
Gangsters | Juuza Amakusa | Rena Ryuuguu | Rina Mamiya | Shion Sonozaki | Shirou Hanada | Staff Leader | Tamae Hojo | Teppei Hojo

Tokyo
Commanders: Miyo Takano | Nomura
Nail Ripper

Yamainu
Okonogi Tetsurou

Others
Oyashiro-sama

Umineko: When the Seagulls Cry
Witches
Beatrice | Bernkastel | Eva-Beatrice | Featherine Augustus Aurora | Lady Lambdadelta | Virgilia | Yasu

Chiester Sisters Imperial Guard Corps
Chiester 00 | Chiester 45 | Chiester 410 | Chiester 556

Demons
Gaap | Ronove

Earls of Hell
Furfur | Zepar

Eiserne Jungfrau
Leader: Dlanor A. Knox
Cornelia | Gertrude

Seven Stakes of Purgatory
Asmodeus | Beelzebub | Belphegor | Leviathan | Lucifer | Mammon | Satan

Ushiromiya Family
Patriarch: Kinzo
Eva | Kyrie | Rosa | Rudolf

Others
Black Battler | Erika Furudo | Kasumi Sumadera

Higanbana No Saku Yoru Ni (unofficial)
Humans
Hikaru Nihei | Nafumi Shintani | Yoshihito Kanamori

Yokai
Higanbana Odoru