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1* CompleteMonster: Here are the worst that [[CowboyCop John "Sleepy" Estes]] ("Mad Bull") and [[ByTheBookCop Daizaburo "Eddie" Ban]] have faced:
2** "Hit and Rape" arc: The owner of the Derringer Club is a man who ostensibly trains women to use guns for self-defense, only to purposefully sabotage them and sell their locations to thugs so they can ambush, rape and sometimes murder them. When an outbreak of these rapes occur, the gun shop owner decides to personally assault a famed TV personality and murder her entire crew before killing her as well.
3** "Charging Jackie" arc: Morley Edwards is a wealthy businessman who is a brutal SerialRapist, responsible for at least 12 rapes and [[SerialKiller murders]]. Whenever he is held accountable legally, he simply murders the witnesses to skate free of justice. When reporter "Charging" Jackie challenges him, he tries to CarBomb her and has her beloved [[MicrowaveTheDog cat roasted alive in the microwave]] before hiring assassins to kill her, with zero regard for collateral damage.
4** "Golden Soldier" arc: [[NamesToRunAwayFromReallyFast Deathmask]] Callahan murders Warden Water and takes over his prison from the inside. Developing the Golden Soldier to better assist assassins in claiming victims so he can take a part of the cut, Callahan takes over his prison, keeping the female prisoners as {{sex slave}}s and ruling via an iron fist. Torturing and murdering two undercover officers in the prison, Callahan later has a person butchered to show off how dangerous one inmate is, murders one of his own men for commenting on how powerful Sleepy is and tries to cheat in the rules of the established fights, resulting in the death of Eddie's beloved Perrine.
5* CrossesTheLineTwice: The entire thing can be considered this, what with all the {{gorn}}, rape and gratuitous swearing in the dub. But nothing prepares you for Sleepy's grenade jockstrap.
6* HarsherInHindsight:
7** It BookEnds with the World Trade Center; even WebVideo/BennettTheSage considers it uncomfortable...and then ''Mad Bull 2000'' blew up the Statue of Liberty in the fall of 1999. This is a running problem with Koike since his early 1970s work ''Mokuyobi No Rika'' when he pictured an assault on the Munich Olympic Games.
8** Sleepy's CowboyCop tendencies. With incidents of police brutality growing more mainstream in the 2000's, his brutality can be rather uncomfortable to watch, even if the people he kills are unrepentant murderers who kill defenseless people and animals and rape women out of their twisted and sadistic personalities, among other atrocities.
9* SugarWiki/HeartwarmingMoments:
10** Sleepy carrying around a bunch of kittens in his hands. Never before has a bulldozer of a cop who regularly blows criminals to pieces with a wide enough variety of firearms to make an entire platoon of soldiers burst into tears of joy been so bizarrely adorable.
11** [[spoiler:Nickel's death, of all things in the 30th Chapter "Goodbye - Ya Con Dios". Long story short, Nickel is finally wasting away and dying from his diabetes, but instead of receiving a gory death, Sleepy actively rescues him from getting crushed to death underneath the rubble from a bunch of buildings set to explode, and, finally at death's door, Nickel admits to John's face that he's grown to respect him and actually gave up on killing him a long time ago because of this, all while crying tears of joy after having gotten the one-up on Sleepy, even if he didn't ice him like he said due to him giving up on killing him, and downright tells Sleepy he's a great person and certainly grew to think of him as a friend before gently passing away with a serene look on his face, and, to pay their last respects to Nickel, they bring him to a cathedral to give him a proper funeral, laying him down on a bed of flowers and suspending a light-up halo over his head, before a crying Sleepy tells him in complete and utter sincerity; to join the angels, the last moments between the Mad Bull and The Electrician not as arch-rivals, but as two men who have grown to consider eachother friends, even if for a moment.]]
12* HilariousInHindsight:
13** While the Cop Killer's outfit is inspired by the works like ''Franchise/{{Alien}}'' and ''Franchise/{{Predator}}'', nowadays it looks remarkably similar to the Green Goblin armor from the first ''Film/SpiderMan1'' movie.
14** Even more humorously, when Sleepy first confronts the Predator-lookalike Cop Killer, he is wearing a Hockey mask that gives him a degree of resemblance to [[Franchise/FridayThe13th Jason Voorhees]]. Several years later, Jason and Predator can be pitted against each other in Videogame/MortalKombatX.
15* LGBTFanbase: Sleepy has a notable following among fans of the BaraGenre, due to being a manly man who is shredded to all hell and back.
16* ObviousJudas: Lieutenant Tom [=DiMeyer=]. The narrative would have viewers believe he was just a strict and tough boss who did whatever was necessary to get the job done, but he goes so far out of his way to KickTheDog and just be unpleasant in general that most viewers will have him pegged as a traitor before he even gets 5 minutes of screen time. Hell, even the ''characters themselves'' seem to be completely unsurprised by his eventual betrayal to the episode's BigBad halfway through the story.
17-->'''Perrine:''' I should have known you were a crook.
18-->'''[=DiMeyer=]:''' Yeah you should, Don Enrico pays more than the police department.
19* SoBadItsGood: It's an early 90's anime, back before anime hit it big in the States, and thus has a really hilarious English dub to go with the equally ridiculous bloody action contained therein. It definitely fits this trope.
20* SugarWiki/SuperlativeDubbing: In original Japanese audio track, when Daizaburo said he wasn't interested in a prostitute Sleepy was eyeing, Sleepy asked him if he's not interested ''even in her'', but in the English dub he asked him whether he's a ''faggot''.
21* UnintentionallyUnsympathetic:
22** Sleepy. In episode 4 of the anime we find out that he turned in his old partner and best friend despite his sympathetic criminal motivations, which results in him quitting the force and ending up killed by the local mob. The justification he gives for this is that he has to uphold the law no matter what and can't make a concession that would be illegal. This is all well and good... except for the fact that Sleepy is a CowboyCop of the highest order who doesn't think twice about blowing away any criminals he encounters with deadly force or using his prostitution money to help fund counseling centers for victims of crime. In other words, he comes off as a complete hypocrite who gets several of his comrades killed despite being perfectly willing to bend the law himself. This is the guy the viewers are supposed to be rooting for?
23** The Capricorn Killer herself counts as well. She's supposed to be a tragic individual who lost everything when Sleepy turned in her brother and decided to lash out in revenge. The problem is she goes after several innocent cops who were just doing their jobs rather than the guy who caused her suffering to begin with. When she does finally confront Sleepy she can't bring herself to kill him and instead just has sex with him before running off to murder the mobsters who actually carried out her brother's execution. While her backstory is certainly sad its very hard to truly sympathize with someone who so nonchalantly murdered potentially dozens of cops while turning a blind eye to the people who were really at fault for her misery.
24* ValuesDissonance: Sleepy's extreme CowboyCop tendencies were already a pretty tough sell to people who believed in due process back in the 90s, but with the new 10s and ''especially'' the new 20s bringing increased attention to PoliceBrutality and corruption in law enforcement Sleepy's antics become a much harder pill to swallow... and that's before getting into the series's treatment of women and minorities, which includes such tropes as MissingWhiteWomanSyndrome, DisposableSexWorker, and ScaryBlackMan. Given that it's a view into the life of American police officers in [[TheBigRottenApple crime infested New York city]] as written by Japanese writers this was almost impossible to avoid.
25* ValuesResonance: On the other side of the coin, it's portrayal of sex workers is surprisingly humanizing, given that they're all portrayed as sympathetic characters.

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