 If you liked
Great Pretender
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 ...then you might like
Fugou Keiji: Balance:Unlimited
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Both of these have a main duo with contrasting personalities, resulting in a fun dynamic. There are jazzy themes, with a western aesthetic. Both require suspension of disbelief but in a really fun way that only adds to your enjoyment; Great Pretender with the con artist skills and Fugou Keiji with Daisuke's expensive gadgets.
Both main protagonists involuntary team up with second main protagonists who are skillfully better than them, and are thrown into a bigger world of crime. Whether it’d be having an unlimited financial balance or expert con-artists skills (or maybe both), their dynamic personalities will soon create a special bond that’ll surely make a name for themselves in their action-packed worlds.
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Recommended by TheHappyMedium
-both are funny
-both have main male leads with contrasting personalities
-both have side stories that continuously evolve and are tied up by the end
-both are rather short
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Recommended by NotLeviosah_
both shows are about a virgin main character who get bossed around by some rich bitch dude
except great pretender does it better
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Recommended by needfoundfamily
the character interactions and hijinks are very reminiscent of each other, along with the way the story plays out.