Bakabon Osomatsu no Karee wo Tazunete Sansenri

Every cinema or direct to video anime film that came out in 1991.

1990: https://myanimelist.net/stacks/34459
https://myanimelist.net/stacks/34460
1992: https://myanimelist.net/stacks/34702
https://myanimelist.net/stacks/34703

Part 2: https://myanimelist.net/stacks/34463

Disclaimer: There are a few hentai movies, that could be counted as well:
- Choujin Densetsu Urotsukidouji 2 (1991)
- Koushoku Ichidai Otoko (1991)
- U-Jin Brand (1991)
- Violence Gekiga Shin David no Hoshi: Inma Densetsu (1991)

Matsuno Brothers (Oldest to Youngest):
1. ❤️ Osomatsu (Signature Color: Red) - The "miraculous idiot."
2. 💙 Karamatsu (Signature Color: Blue) - The "cool idiot."
3. 💚 Choromatsu (Signature Color: Green) - The "reasonable idiot."
4. 💜 Ichimatsu (Signature Color: Purple) - The "pitch-black idiot."
5. 💛 Jyushimatsu (Signature Color: Yellow) - The "of-another-dimension idiot."
6. 💗 Todomatsu (Signature Color: Pink) - The "good-at-letting-others-pamper-him idiot."
(Source: Osomatsu Wiki https://osomatsu.fandom.com/wiki/The_Sextuplets)

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Osomatsu-san Watch Order:
* 1. Osomatsu-kun (Feb 5, 1966 to Mar 25, 1967) | TV | 56 episodes × 25 min. per ep. - Alternative Version
2. Osomatsu-kun (1988) (Feb 13, 1988 to Dec 30, 1989) | TV | 86 episodes × 24 min. per ep. - Alternative Version / Parent Story / Character / Prequel
3. Osomatsu-kun (1988): Appare! Chibita no Onitaiji zansu (Dec 31, 1988) | Special | 1 episode x 50 min. - Side Story
4. Osomatsu-kun: Suika no Hoshi kara Konnichiwa zansu! (Mar 18, 1989) | Movie | 1 episode × 25 min. - Side Story
5. Osomatsu-kun: Iyami wa Hitori Kaze no Naka (Aug 25, 1990) | OVA | 1 episodes × 25 min. - Side Story
6. Bakabon Osomatsu no Karee wo Tazunete Sansenri (Oct 19, 1991) | Special | 1 episode × 44 min. - Character
* 7. Osomatsu-san (Oct 6, 2015 to Mar 29, 2016) | TV | 25 episodes × 23 min. per ep. - Sequel / Parent Story / Other / Fulll Story
8. Osomatsu-san Short Film Series (Jan 29, 2016 to Jul 29, 2016) | Special | 7 episodes × 2 min. per ep. - Side Story / Prequel
9. Osomatsu-san Special (Jan 29, 2016) | Special | 1 episode × 21 min. - Side Story
10. All-Free kono Natsu Ichioshi Monogatari Campaign Kokuchi Douga (Jun 21, 2016 to Jul 12, 2016) | ONA | 12 episodes × 42 sec. per ep. - Other
11. Matsumotokiyoshi x Osomatsu-san (Jun 25, 2016 to Dec 18, 2017) | ONA | 9 episodes × 42 sec. per ep. - Other
12. Tokyo Girls Collection 2016 A/W x Osomatsu-san Special Movie (Sep 3, 2016) | Movie | 1 episode × 2 min. - Other
13. Hashire! Osomatsu-san (Oct 2016 to Dec 2016) | Special | 3 episodes x 30 sec. per ep. - Other
14. Mutsugo to Ouma no Monogatari (Oct 13, 2016 to Dec 8, 2016) | ONA | 6 episodes x 2 min. per ep. - Other
15. Osomatsu-san: Ouma de Kobanashi (Dec 13, 2016) | TV Special | 1 episode x 24 min. - Other
16. Osomatsu-san: Haru no Zenkoku Dai Senbatsu Jouei-sai - Sentou Quiz 2 (Apr 6, 2017) | Movie | 1 episode x ? - Side Story / Summary / Other
* 17. Osomatsu-san 2nd Season (Oct 3, 2017 to Mar 27, 2018) | TV | 25 episodes x 23 min. per ep. - Sequel / Other / Parent Story / Spin-off / Prequel
18. dMatsu-san (Jan 9, 2018 to Mar 27, 2018) | ONA | 12 episodes x 1 min. per - Side Story
19. Osomatsu-san Short Film Series 2nd Season (Jan 26, 2018 to Jul 27, 2018) | Special | 4 episodes x 5 min. per ep. - Sequel / Other
20. Osomatsu-san: Hajimaru Hajimari (Aug 2, 2018) | 20 | 6 episodes x ?
21. Osomatsu-san x Mameshiba (Mar 27, 2018 to Mar 20, 2019) | CM | 2 episodes x 30 sec. per ep.
22. Osomatsu-san Movie: Gekijou Koukai Kinen - Original Tanpen Gekijou (Mar 1, 2019 to Mar 15, 2019) | ONA | 7 episodes x 2 min. per ep.
23. Osomatsu-san Movie - Parent Story (Mar 15, 2019) | Movie | 1 episode x 1 hr. 48 min. - Other
24. Osomatsu-san Movie: Zensetsu Gekijou (Mar 15, 2019 to Apr 19, 2019) | Movie | 6 episodes x 2 min. per ep. - Other
* 25. Osomatsu-san 3rd Season (Oct 13, 2020 to Mar 30, 2021) | TV | 25 episodes x 23 min. per ep. - Sequel / Parent Story / Prequel
26. Atsumare! Minna no Kontematsu-san! (Dec 25, 2020 to Jul 23, 2021) | Special | 8 episodes x 1 min. per ep. - Side Story
* 27. Chocomatsu-san: Valentine's Day-hen (Feb 13, 2021 to Feb 15, 2021) | ONA | 3 episodes x 4 min. per ep. - Other / Side Story / Prequel
28. Chocomatsu-san: White Day-hen (Mar 13, 2021 to Mar 15, 2021) | ONA | 3 episodes x 4 min. per ep. - Other / Side Story / Sequel
29. Osomatsu-san: Hipipo-Zoku to Kagayaku Kajitsu (Jul 8, 2022) | Movie | 1 episode x 1 hr. 7 min. - Other / Sequel / Prequel
30. Osomatsu-san: Tamashii no Takoyaki Party to Densetsu no Otomarikai (Jul 21, 2023) | Movie | 1 episode x 58 min. - Other / Sequel
31. Matsuinu (Oct 7, 2023 to Dec 23, 2023) | TV | 12 episodes x 2 min. per ep. - Spin-off
32. Osomatsu-san Shinsaku Short Anime (Sep 11, 2024 to ?) | ONA | 4 episodes x 1 min. per ep.
33. Osomatsu-san 4th Season (Not yet aired) | TV - Sequel

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*Live-action film
Eiga Osomatsusan (featuring SnowMan)
https://osomatsusan-movie.jp/
https://www.imdb.com/title/tt15162634/
https://osomatsu.fandom.com/wiki/Osomatsu-san_Movie_(Live_Action)
https://mydramalist.com/707455-mr-osomatsu

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Genre: Comedy
Theme: Gag Humor
Demographic: Shounen

Tags: Osomatsu-kun, Osomatsu-san, Chocomatsu-san, Pierrot, Akatsuka Fujio, Brothers, Siblings, Sextuplet, Franchise

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Official Sites:
https://osomatsusan.com
https://osomatsusan-fc.com/

Fandom Wiki: Osomatsu Wiki https://osomatsu.fandom.com/wiki/Osomatsu_Wiki

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Included in: Largest Anime Franchises
https://myanimelist.net/stacks/20094

Club: Osomatsu-san FC『おそ松さん』 https://myanimelist.net/clubs.php?cid=69668 (Inactive)

✔️。

Part 2 - https://myanimelist.net/stacks/35023

See also separate stack for Mameshiba crossovers - https://myanimelist.net/stacks/35020

Crossover of shounen anime franchises.

Demographic: Shounen

Tags: Collaboration, Crossover, Shounen

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Manga counterpart:
Shounen Crossovers, check: https://myanimelist.net/stacks/9874

For more crossover anime, check the Crossover thread in the Interest Stacks Repository club:
https://myanimelist.net/forum/?topicid=2172644