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Crying Freeman

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2.619 out of 5 from 217 votes
Rank #1,663
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Synopsis:

Once a humble potter, Freeman saw something he should not have seen. As a result he was stripped of his name and his freedom, forced to work as an assassin for the Chinese Mafia known as the 108 Dragons. Due to his flexible body and quick reflexes he quickly rose to be the top assassin of the syndicate. Each time he kills, he cries - earning him the name Crying Freeman. Despite being stripped of his freedom by the syndicate they were unable to prevent him from falling in love; can Freeman escape from the syndicate that trained him while keeping his lover alive?

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Golgo 13: The Professional

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Golgo 13 is the codename for one of the world's most deadly hit men, a man whose identity is unknown and sought after. After a routine hit on the son of a wealthy oil tycoon and a shadowy figure known as Dr. Z, Golgo 13 soon finds himself on the other side of the gun barrel, being pursued by a mysterious organization whose deadly plans involve killing the man himself. With little time and lots of ammo, Golgo 13 must pursue his would-be killers, while simultaneously trying his best to stay alive!

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Funkgun

Assassins?

Older anime?

Short length?

 If you are so inclined to see a story of the seedy underworld, and what it is like to be a person who kills for his profession you can not go wrong here. Both titles have some good ol blood and guts and are more adult in nature.