Total Recommendations: 2
If you liked
Monster
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...then you might like
Gyakkyou Burai Kaiji: Ultimate Survivor
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Thriller anime that gets you into the mind of the protagonist, though Monster is more one story while Kaiji is more separated into multiple arcs
If you liked
School Rumble
|
...then you might like
Kaguya-sama wa Kokurasetai: Tensai-tachi no Renai Zunousen
|
Great comedies with similar casts, separated in 3 parts and similar humor. School Rumble inspired Kaguya-sama