An East Asian triad organization led by a group called The Van. The Van are usually seen wearing imperial Manchurian-Chinese clothing of the Qing dynasty. The syndicate specializes in assassinations, but are also involved in the trafficking of narcotics, Red Eye in particular. The rules of the syndicate states that members who attempt to leave, or fail to complete tasks, are punished by death. Mao Yenrai served as a captain or Capo to the Elders and was a mentor to both Vicious and Spike.

After leaving the Syndicate, Spike considers himself in Mao's "debt", and is motivated to confront Vicious for the first time when Mao is killed by two men in Vicious' employ. It takes place immediately after Mao signs a peace treaty with a rival crime syndicate, the White Tiger, expressing a desire for relief from the hypervigilance of gang warfare. The Van later refers to Mao's death as "bad luck" and decline to pursue the issue when confronting Vicious. The Van is also shown to be indulgent toward Vicious initially, which eventually creates their demise. Vicious kills the Van and becomes the head of the Syndicate.
Voiced by: Norio Wakamoto (Japanese); Skip Stellrecht (English) Portrayed by: Alex Hassell

"Vicious" (ビシャス, Bishasu) is the main antagonist of the 1998 anime series Cowboy Bebop, and Spike Spiegel's archenemy. He is a ruthless, cunning, power-hungry, and cold-hearted member of the Red Dragon Crime Syndicate in Tharsis, and is often referred to or depicted as a venomous snake (as opposed to Spike who is referred to as a swimming bird and the Syndicate Elders who see themselves as a dragon). His weapon of choice is a katana which he wields skillfully, even against gun-wielders. He was an infantry rifleman during the Titan War and is shown firing a semi-automatic pistol in a Session 5 flashback, as well as in the Session 26 flashback of him and Spike fighting back-to-back. Vicious is usually seen accompanied by a black cormorant-like bird. He eventually hides explosives in its stomach and detonates them as a distraction during an escape.

Vicious was Spike's partner in the Red Dragon crime syndicate until they fell into conflict over Julia. After Spike's supposed death, Vicious left the Red Dragons briefly to fight in the Titan War of 2068. Although his precise motivations for enlisting are debated, his testimony helped frame Gren, his squadmate in the war, for spying, which raises the possibility that he himself might have been involved in military espionage on behalf of the Syndicate and chose to pin it on his admirer. However, in the Titan flashbacks he is also seen to be remembering Julia.

Vicious believes that he is the only one who can kill, or "awaken" Spike, as Spike is the only one who can do the same for Vicious. Vicious's real age is revealed in the official guidebook The After: at 27, he is the same age as Spike. The age 27 is significant in the series because of the connotations it has to some legendary musicians passing away at that age, who are called the 27 Club. He appears much older due to his gray hair and the heavy, ever-present bags under his eyes.
Voiced by: Gara Takashima (Japanese); Mary Elizabeth McGlynn (English) Portrayed by: Elena Satine

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Voiced by: Kenyu Horiuchi (Japanese); David A. Thomas (English) Portrayed by: Mason Alexander Park

Grencia Mars Elijah Guo Eckener (グレンシア・マルス・エリヤ・郭・エッケナー, Gurenshia Marusu Eriya Guo Ekkenā), also simply referred to as Gren (グ レ ン, Guren), was a soldier for the war on Titan, and appears in the two-part episode "Jupiter Jazz". On Titan he fought beside Vicious, whom he admired and found encouragement in. After the war, Gren came back hoping to be a jazz musician, but he was arrested as a spy. In prison, Gren heard that Vicious testified against him; this and the isolation drove him mad. The prison conducted drug experiments on him. In some translations, he suffered from insomnia while in prison and started using drugs to deal with it. In either case, the drugs severely imbalanced his hormones, causing him to develop a feminine figure, including breasts. After escaping from jail, Gren worked as a saxophone player at Rester House, a bar in a sector called "The Blue Crow", which is located on one of Jupiter's moons, Callisto. He met Julia there and found out from her how Vicious betrayed him.

Two years later, Gren rescues Faye from a street fight and takes her to his apartment. While Faye is there, Vicious calls, raising suspicions about Gren. Intruding on him while showering, Faye discovers Gren's secret. Gren explains his background, and tells her that he is going to see if Vicious really framed him. Disguising himself as a woman, Gren meets Vicious and Lin. Exchanging Red Eye for Titan Opal, Gren suspects a trap. He shoots it open, setting off the explosive, and then reveals who he is. In the ensuing battle, Lin dies to protect Vicious. Spike arrives and attacks Vicious. Gren had planted an explosive in the bag of Red Eye, which damages Vicious' ship. In the 4-way dogfight with Vicious and Spike, Gren's ship is severely damaged, forcing him to land. Spike lands next to Gren's ship to find Gren lying in the snow, badly wounded. Gren guesses who Spike is by his eyes; "Julia was always talking about you; your eyes are different colors. I remember her saying that". Gren requests that Spike help him back into his ship and tow it out into space, allowing him to die on a final voyage to Titan.
Punch – Voiced by: Tsutomu Tareki (Japanese); Paul St. Peter (English) Judy – Voiced by: Miki Nagasawa (Japanese); Lia Sargent (English) Portrayed by: Ira Munn (Punch); Lucy Carrey (Judy)

Punch (パンチ, Panchi) and Judy (ジュディ, Judi) are the hosts of the TV show Big Shot. They are named after the traditional English puppet show. The show provides information on various bounty heads, but is often unreliable. The Bebop crew often has the show playing in the background, but seldom pays close attention (they usually get their information from close contacts). Punch and Judy play the "cowboy" persona in a characteristic, over the top fashion. Punch adopts a mid-western drawl mixed with a Mexican accent (both faked), and uses random old-West sayings. Judy plays the stereotypical dumb blonde, and always appears in an open bolero jacket with nothing underneath, frequently wiggling her hips with excitement. Big Shot is canceled towards the end of the series. Punch, lacking accent and costume, makes a cameo revealing his and Judy's fates: Punch, whose real name is Alfredo, moves to Mars to take care of his mother, and Judy is engaged to her agent, Cameron Wilson.

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Voiced by: Tomie Kataoka (Japanese); Melodee Spevack (English)

Victoria "V.T." Terpsichore is a tough-talking space trucker whose deceased husband, Ural Terpsichore, is a legendary bounty hunter. Always with her cat, Zeros, she appears in the episode "Heavy Metal Queen". Spike meets her in a bar while on hunt for an explosive-smuggling criminal named Decker. After having a bar brawl with several stooges, Spike and V.T. seem to become fast friends until she learns Spike is a bounty hunter. Although she regards Spike as "lowlife bounty hunter scum", she puts their differences aside and reluctantly works with him when their paths cross again as V.T. begins searching for Decker, who has performed a ship hit and run on one of her fellow truck drivers.

Her full name is largely a secret, which has prompted many to bet money and guess what her initials stand for. She is also known as the "Heavy Metal Queen", for her love of heavy metal music, which she considers "very soothing". Able to adapt to various situations, her philosophy is "When in Rome, do as the Romans do". Considering her disdain for bounty hunters, it is believed that her husband was killed while pursuing a bountyhead.
Voiced by: Ryūsei Nakao (Japanese); Tom Fahn (English)

Rocco Bonnaro (ロコ・ボナーロ, Roko Bonāro) is a member of Piccaro Calvino's gang. He is involved in organized crime to support his blind younger sister, Stella Bonnaro (ステラ・ボナーロ, Sutera Bonāro). Rocco sees Spike effortlessly take out several hijackers on a spaceliner and begs Spike to teach him how to fight. He befriends Spike although he does not tell him about the bounty on his head. Rocco gives Spike a package to hold onto, which contains a plant called "Grey Ash" that he stole from Calvino. This plant, worth millions of woolongs, is capable of curing "Venus Sickness", the disease which has blinded Stella. Rocco has a rendezvous with Spike and they fight Calvino's gang. Rocco pulls off one of Spike's Jeet Kune Do maneuvers and topples one of the gangsters, but is gunned down. Later, Spike pays his respects and visits Stella in the hospital where she is receiving treatment to tell her that Rocco has died. Before he leaves, Stella asks Spike about the type of person her brother really was. Spike responds, "You know better than anyone, without looking. He was a terrific guy – exactly the person you thought he was."
Voiced by: Takeshi Watabe (Japanese); Michael McCarty (English)

Hex is a talented programmer widely considered to be a genius due to his long-standing hold of the Champion Seat of the CosmoNet Chess tournament series. At the age of 30 he joined the Hyperspace Gate Project and, ultimately, played a key role in the development of the central control system used in all gates. However, Hex soon began to have doubts about the functionality of the control system, believing it to have defects. Upon discovering that these defects were intentionally added by the Gate Corporation to ensure further revenue, Hex developed a plan to be executed 50 years in the future that would allow criminals to hijack the Astral Gate toll booths.

In the episode "Bohemian Rhapsody", Spike, Jet and Faye track down Hex following the failed toll booth hijackings. Hex, now old and senile, is living peacefully inside of a bohemian junk heap floating in outer space. Given that h…

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