Crying Freeman OVA in order

Crying Freeman follows a Japanese assassin hypnotized and trained by the Chinese mafia (called the "108 Dragons") to serve as its agent, and covered in a vast and complex dragon tattoo. A quiet but complicated killer, Freeman reflexively sheds tears after every killing as a sign of regret. 6 films, 5h 15m in all, in release order.

Crying Freeman 1: Portrait of a Killer
1988 · 60 min
Emu Hino, a 29-year-old virgin, witnesses a mob hit and fears that the killer will now find her and kill her. Indeed, he sets out to do so; he's Yo Hinomura, a talented potter and artist who's been conscripted against his will to be the prime hitman for the 108 Dragons, a gang within the Chinese Mafia, who are determined to push aside Tokyo's local crime lords. He breaks into her house, and she asks that he make love to her before he kills her; she connects to his inner self, and he becomes her protector. Now he must defend her against the local crime gang, who have connections with corrupt Tokyo police. Will Yo and Emu make it out alive, and will the 108 Dragons triumph?
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Crying Freeman 2: Shades of Death, Part 1
1989 · 50 min
With the blessing of the 108 Dragons, Yo and Emu marry and receive new names, Ron Tayan and Fu Ching Ran. The elders send them to Macau to find out who's behind a new attack. Fu is kidnaped; at the same time, Baya San (the huge granddaughter of the 108 Dragons' aged leaders) demands to be the next head of the gang, not Ron. The childish Baya San has joined forces with the Macau gang, in league with the American mob. A surprise visitor from the US arrives where Fu is being held captive. Can Ron rescue her, find the traitor within the 108 Dragons, defeat his enemies, and bring discipline to Baya San? He must still face the angry and deadly girlfriend of the American visitor.
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Crying Freeman 3: Shades of Death, Part 2
1990 · 55 min
Ron Tayan now leads the 108 Dragons; Fu Ching Ran is his loyal wife. As their body tattoos show, he's the dragon, she's the tiger. The 108 Dragons are attacked by African Tusk, a syndicate intent on world control. Ron goes to Africa, dealing first with Shicaro, African Tusk's assassin, then with Jagone, its leader. Despite his success, he must still face Bugnug, Jagone's muscular and athletic military commander: Ron gives her a new name, Dark Eyes. Back in Hong Kong, Fu faces danger as well. A Muramasa sword with a dark history and, seemingly, its own demon spirit, falls into her hands. She seeks to tame it, and in the process, discovers her inner warrior identity
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Crying Freeman 4: A Taste of Revenge
1991 · 50 min
Naitai, the evil head of the Great Bear God religion, hatches a plot to destroy the 108 Dragons. His henchman, Oshu Togoku, the world wrestling champion, squeezes Ron Tayan unconscious in a match; the ambulance taking Ron to hospital is actually driven by Kimie, one of Ron's old enemies. She takes him to Naitai's stronghold where he has prepared a clone of Ron whom he intends to send, like a Trojan horse, onto the yacht of the 108 Dragons. Can Ron foil the plot? Will Fu recognize the clone or be fooled? What of Oshu Togoku, can anyone defeat him? And who, or what, can stand up to Naitai's sorcery?
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Crying Freeman 5: Abduction in Chinatown
1992 · 50 min
In L.A.'s Chinatown, the crime cartel known as K.O. hatches a plot to bring down Ron Tayan and the 108 Dragons. Ron joins forces with the computer-savvy daughter of the local boss; she tracks the attacking gang via electronics, Ron goes to their stronghold via plane. They are kidnapers of young children, using ransom money to fuel their other activities. The troops are ex-Green Berets; the leaders are Larry Park, an expatriate Yank, and Nina Heaven, a killer with a soft spot in her heart for Ron. He's her captive, but she wants him to be her partner. Meanwhile, Fu, armed with her Muramasa sword, and Dark Eyes arrive on the island surreptitiously. The battle lines are drawn.
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Crying Freeman 6: The Guiding Light of Memory
1994 · 50 min
CRYING FREEMAN: FINAL CHAPTER -- THE GUIDING LIGHT OF MEMORY (1993) is the sixth and last volume in the OAV series of Japanese anime adaptations of the "Crying Freeman" manga. A hard-hitting tale of violent criminals engaged in a brutal turf war, it is easily the best-written and most stylishly directed since the first in the series (PORTRAIT OF A KILLER). This one tells the story of a young Japanese Yakuza who takes over the Russian supply of drugs and weapons to Japan and cuts out the involvement of the Hong Kong-based 108 Dragons. Freeman, the hitman of the title and the 108 Dragons' star player, goes to Japan to investigate and gets framed for a succession of assassinations of top Yakuza bosses. The chief enemy here, Tsunaike, is aided by an icily sexy Arctic hit lady, Tanya (described as "Eskimo" in the subtitles, although she looks more Siberian), who is frequently seen in the nude in regular trysts with Tsunaike.
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Frequently asked questions

What order should I watch Crying Freeman OVA in?

1. Crying Freeman 1: Portrait of a Killer (1988), 2. Crying Freeman 2: Shades of Death, Part 1 (1989), 3. Crying Freeman 3: Shades of Death, Part 2 (1990), 4. Crying Freeman 4: A Taste of Revenge (1991), 5. Crying Freeman 5: Abduction in Chinatown (1992), 6. Crying Freeman 6: The Guiding Light of Memory (1994).

How long does it take to watch all of Crying Freeman OVA?

About 5h 15m across 6 released films.

Do any Crying Freeman OVA films have post-credit scenes?

None are listed on TMDB.