The first time we are introduced to Umibozu's worst fear: cats. The cuter they are, the more Umibozu fears them.
The first time we get a good look at Umibozu after he was named: Ryo and him were having breakfast (paid by Ryo) after he had been caught placing a bomb on the car of Ryo's charge the actress Yumiko Sato!
It gets better at the end of the story arc: Yumiko had hired Umibozu to kill herself, and when she was finally convinced to shoot Umibozu and live we discover that the breakfast had actually been Ryo bribing him to have his help, and that Umibozu had let himself being bribed because he was a fan of Yumiko!
Ryo and Umibozu's trolling of the movie that was being shot. It started with Ryo interrupting the shooting for senseless reasons (and to check if the killer had poisoned a cake on the scene), then he was in Yumiko's bed when the male lead came to try and seduce her (Yumiko had asked Ryo to make sure he stopped harassing her, so Ryo invited him in the bed using her voice. The male lead was scarred for life), and then interrupting the shooting because the lead actor was holding a gun the wrong way... And to troll him again. Then, when the director finally got Ryo to stop, Umibozu replaced all the fake weapons on the scene with actual guns (including a bazooka) and dropped a building on Ryo and Yumiko just to make some chaos and shoot Yumiko while nobody was looking. Finally there's the final scene, where Umibozu shows up to fake a last attempt and help Ryo getting Yumiko to live... And so tries and run her over with an 18-wheeler while shooting a machine gun at Ryo. The poor director was crying after the last one...
Ryo had been hired to fake the death of a man, so he swapped place with a man hired to kill his client. To do so, he called the killer and, imitating the voice of the client, told him that the meeting place had been changed to Hachiko's statue (specifically he told the killer to sit on the statue, and to hold a Rika-chan doll to be recognized! He waited for his client for hours sitting on Hachiko's statue while holding the doll...
Becomes even funnier when that killer reappears as Umibozu.
Sayaka Ryujin's arc sets the change from a dark series to a much funnier one... And is made of CMOF.
It starts with the head of the Ryujin Yakuza gang inviting Ryo and Kaori to a pool to try and hire them as bodyguards... With Kaori complaining all the time about his lack of manners and that he looked like a Tanuki instead that being charming as the Yakuzas of the movies.
In the end the talks break down, so Ryujin ends in the pool and Ryo takes the 100 millions yen he would get for the job. A week later Ryujin calls and tells him to give him back the money or do the job, and Ryo unwillingly accepts out of sense of duty. Of course Kaori asks him why he can't just give him back the money, and at Ryo's answer she replies "YOU ALREADY SPENT THEM?! YOU SPENT ONE HUNDRED MILLIONS YEN IN A WEEK?!".
Ryujin shows Ryo his job: he'll have to be a bodyguard for his daughter Sayaka, a senior high school student. First thing Ryo does is to ask him if he adopted her, as she's gorgeous and Ryujin looks like a tanuki.
Why does Sayaka need a bodyguard? Because she's the leader of a delinquent gang, and had just sent in hospital the leader of a biker gang, and left her father's home because she hates the Yakuza (not that it stops her from letting daddy pay for her apartment and livings). So Ryo has to go at her home and fake being a private tutor.
Sayaka's attempts at making Ryo run away fail miserably before him being a Crouching Moron, Hidden Badass who can easily deal with her gang, and Sayaka has only five millions yen in her banking account so she can't pay Ryo's debt.
Sayaka decides to get Ryo in trouble with Kaori, so tries and seduce him a few moments before she stopped by, and, when rebuffed, started crying in terror to make Ryo look like a rapist. Too bad that Ryujin was spying on Sayaka, giving Ryo a witness.
Ryujin Boss: "Saeba! Why did you refuse my daughter?!"
Ryo lets the biker gang kidnap Sayaka so he'll find their boss and deal with him... Only to discover he's a dwarf who uses a much bigger lookalike as spokesman (even before his gang, who knows about him) and is engaged to Sayaka, who sent him to the hospital for copping a feel. He's also the son of another Yakuza boss, but hates the Yakuza and made his gang a biker gang with English names... And punishes them in Yakuza style when they call him Number 2 or use their real names. That's when Ryo shows up, humiliates the entire gang and tells Sayaka's father that he doesn't want to marry her as he wanted them to. Too bad she's just fallen for him... And moves in his home while presenting herself as Mrs. Saeba.
Kaori being mistaken for Sayaka's husband.
In their first meeting, Saeko tried to seduce Kaori. Then revealed she could see Kaori's real gender and did it just to screw with her.
One from Kasumi Aso's introductory arc. During the heist she had hired Ryo to help in, Kasumi donned the gymnastic body she wore for her heists. Kaori, having entered a rivalry with her over their beauty, imitated her for added Fanservice... At which point Ryo undressed and revealed he was wearing one too. In a sexy pose. In the manga version the image floored even the author's assistants...
Once Kaori expressed the wish to see, just for once, the message board of Shinjuku station filled with XYZ requests. When she looked at the board she saw a single XYZ filling the whole board. The new client was the gigantic Umibozu, who had left a request of the right size.
In that arc Umibozu hired Ryo to impersonate him with Maki, the daughter of his late commander when he was a mercenary whose musical studies were paid by Umibozu. Of course Umibozu doesn't trust Ryo alone with her... And follows them while they go in town, even shooting at Ryo's erected penis (Ryo saw him fire and 'lowered the penis').
That night Ryo housed Maki. Umibozu placed a series of traps to stop Ryo from getting in her room. Lethal traps, worthy of a true professional mercenary. The final one? Kaori: Maki was sleeping in her room.
Umibozu following Ryo and Maki the day after, wearing the following disguises (all but the duck including sunglasses): a Colonel Sanders statue before a Kentucky Fried Chicken restaurant; an old gigantic lady; a duck (he was under water with a fake duck on the head over the surface); a statue of a cartoon elephant; the statue of a gorilla; the statue of a Buddhist spirit; the bust of Hercules With Sunglasses (it was written on the bust's plaque).
After Umibozu had to reveal himself due a traitorous member of their unit trying to kill Maki in revenge, Maki has a violin concert, to which Ryo sends the biggest flower boquet he could find. Umibozu's was bigger than a car, and signed with his (overly serious) real name Hayato Ijuin. Cue Ryo revealing the origin of the nickname Umibozu (sea monster) and that Umibozu nicknamed him 'Shinjuku's Stallion' in revenge.
Before the concert, Maki asked him if he knew who was targeting her. His answer? "Saeba is a womanizer, and a woman he cheated swore to kill any woman approaching him!", followed by him making a funny pose and declaring "Just kidding" when Ryo protested.
If Umibozu shows up and he's not demonstrating his ability as sweeper, something funny is about to happen. Sometimes his moments of awesomeness are interrupted or complemented by funny ones, like his ability to disguise himself as a duck or that time he decided to juggle with three villains completely out of the blue.
Whenever a foe makes Ryo impotent, his reaction is quite funny. Also, his attempts at recovering his Gag Penis, and how he made both sets of villains impotent.
Ryo's reaction the first time? Declaring he'd go to Morocco to get his gender changed. Kaori told him to not do it, as he'd be a very ugly woman.
When Ryo gets drunk, he tends to bring home strange things. Usually it's women's undergartments, but he may bring home four advertising statues (including a Colonel Sanders' one) and a two years old girl in one go.
Made funnier because the only one he and Kaori were surprised at was the girl...
Ryo's horrified reaction when Yuka Nogami, Saeko and Reika's sister and a Magnificent Bastard in making like her older sisters, told him they had two other sisters (twin, at that), and that their father, being fixated with having a male son, was trying to have other children.
Ever wondered why Saeko is still single, in spite of her gorgeous looks and a father obsessed with having grandchildren? Easy: she refuses to marry a man weaker than herself, and all the six prospective fiancee have been hospitalized by her 'strength tests'.
The seventh was actually stronger than Saeko, but decided it wouldn't work between them and moved out of town. Her father's reaction? "Quick! I must find bridegroom number eight!".
In one story arc, photojournalist Yoko Tono had decided to make City Hunter famous as a hero and wanted to get a picture of his face, so she went to various yakuza who had met him to get a description... With Ryo terrifying the yakuza behind her back. After the obligatory Oh Crap moment, the poor yakuza bolted in terror... Except the one who fainted with a foaming mouth.
Same story arc: Ryo and Kaori's desperate attempts at doing their job (including one for Saeko) while keeping Yoko convinced he's City Hunter's idiot brother Ryokichi and not the great Ryo Saeba.
Near the end, a group of thugs kidnapped Yoko to get revenge on Ryo for beating them up, with Yoko helping them to get City Hunter in the open. Ryo managed to sneak in to free Yoko, but she refused to escape, at which point Ryo left, told the beaten up thugs he'd return in a couple hours and to bring him someone who could fight, and not the Giant Mook their boss had borrowed from his father, a Yakuza boss.
At the moment of the final battle the thugs are armed with guns thanks to the Yakuza boss, and both them and Yoko believe not even Ryo can defeat them, nor the actual Yakuza waiting with their boss in case they're needed. The tension is high... Then Ryo shows up, quoting a tv show about a samurai masquerading as the folk hero Momotaro (his name meaning 'Child of the Peach'), and concludes by presenting himself as Princess Peach, complete with a paper mask (later switched for fake glasses with a big nose) to hide his true face. The Yakuza, after recovering from the Face Fault, complain about theMood Whiplash.
Mick Angel and Ryo are about to duel. Mick throws away his jacket... And then runs to recover it because is expensive and didn't want the wind to blow it away.
Mick during the entire arc. While Ryo and Kaori are too busy dealing with Mick showing to kill the former and woo the latter, plus Kaori finding out that her gun has been sabotaged by Ryo, Mick has no such problems, and pulled things like declaring out loud why he wants to seduce Kaori and his deduction she's a virgin, being prevented from a 'night visit' to Kaori due Ryo tying him up the same way Kaori does to him, getting hammered by reflex by Kaori when he tried to kiss her, and everything he did in his duel with Kaori (including his reaction when Kaori told him she had mined the building and would destroy it if he tried to not fight). And trying and seducing a newlywed woman while waiting for Kaori in the airport's lobby.
After that, Ryo runs to Saeko and demands that she'll let him have sex with her twice instead of the single time already owed. Eran, who is seeing the scene on his security cameras, is disgusted. Then Ryo moons him through the camera.
Eran is chasing Ryo, using his allergy to find where he's hiding. At one point he turns a corner, is about to shoot Ryo... And facefaults at the sight of Ryo wearing half a dozen pairs of woman's panties, two bras and a garterbelt. Upon asking what he's doing, Elran is told that Ryo was trying to cover his male smell...
And let's not forget what Ryo pulled on him before the duel. Upon getting confirmation that every night Elran has sex with a member of his Amazon Brigade, Ryo uses his Voice Changeling abilities to feign being Elran and give a couple tips to the chosen one. Namely, that Elran adores masochistic sex, and that she needs to kick him in the balls as strong as she can and bite him over all his body.
Kasumi Aso returns to try and have Ryo help her getting out of an Arranged Marriage by taking the place of her fiancee. The marriage had been arranged to insure that Kasumi would have many healthy children capable of continuing their dinasty of Phantom Thieves, so Ryo decided to prove he was the most suited... By showing his gigantic erection. Kasumi and the suitor were not amused... But Kasumi's grandmother declared it a valid argument.
The suitor happened to be a skilled hypnotist... So he hypnotized Ryo into believing he had an even bigger one. They go for the theft test.
In one chapter the sweeper Black Lizard attacks Ryo in broad daylight, resulting in a brief shootout in full view of civilians before Black Lizard's escape. How does Ryo get away with it? He declares they were shooting a scene of a movie, and indicated his client as the director. Bonus point for calling the movie City Hunter: Million Dollar Conspiracy, using the title of the third OVA.
From the same arc, the antics of the client, Michihiko Jinguchi, who proudly declares his family as the "Mokkori Family". Not only he's a Dirty Old Man, he's worse than Ryo. There's a good reason if Kaori started believing his claim of being his grandfather...
Umibozu notices it's not clean enough, so he cleans up until the whole coffee house is sparkling... And bent all the stools in the process, not noticing as he's blind now.
A young student comes to get a coffee and admire Miki... And is greeted by Umibozu. Who scares the hell out of him while trying to be nice.
The students gets almost malleted by Kaori, who was chasing Ryo and mistook him for her colleague.
After Kaori left, Ryo drops from the ceiling, and gets roped into helping. The student wants to leave... But Umibozu notices he dropped the coffee when Kaori attacked him, so he offers him another coffee and a sandwich, and tells him to take all the time he needs. Poor student is too scared to run...
Two women enter. At first Umibozu tries to stop Ryo from serving them... And then notices they have a kitten.
The poor student tries to leave... And Umibozu nearly gives him an heart attack when he tries to give him the change.
A bank robber breaks in to take everyone hostage, including the student, Umibozu and Ryo.
Ryo: "Umi, I'll leave him to you. I'm busy with our customers."
Umibozu: "Are you kidding me?! Why should I beat up an amateur?!"
Ryo: "Exactly, it's an amateur. If we ganged up on him we'd be ridiculous."
Umibozu enters awesomeness mode, disarms the robber and grabs him by the head... And the cat gets free. Hilarity Ensues again. And the student swears he won't return.
The punchline? When she returns, Miki says it's better than what usually happens when Umibozu is helping.
Ryo's running gag of claiming he's twenty, born after Kaori learned he didn't know his actual age or birthday and gifted him with a birthday and an 'official' age of thirty. Particularly fun when he was supposed to celebrate his thirty-first birthday... And claimed it was the twentieth.
A particular variant showed up with Saeko: her father was pestering her about her still being unmarried at her age, and she promptly claimed still being twenty.
How does Ryo deal with having rented an apartment to Sympathetic Inspector Antagonist Hirotaka Kitao, who is in Tokyo specifically to arrest City Hunter and has already guessed his identity? Easy: he throws him a welcome party in a gay bar, forcing him to drink alcohol all night long. For two nights in a row. And was planning to continue, but events made Kitao realize that City Hunter was a good person.
At the end of the arc Kitao moves out of Tokyo. How does Ryo say him goodbye? He throws him an all-night farewell party in a gay bar.
Near the end of the series, three of Ryo and Kaori's clients have apparently been stolen by a fake City Hunter, who told the clients to be wary of the call from a fake to squeeze the real ones out of the market. Kaori suspects that Ryo is involved and told the clients there was a fake City Hunter to cover his ass from Kaori, but Ryo insists there's a fake, so they go and survey the message board. As Ryo is in the toilet, a woman starts writing XYZ, is approached by the fake... At which point the woman is revealed to be Ryo in a drag.
And the identity of the fake? Mick Angel, who decided to use the name City Hunter because it was the Collective Identity of Ryo and him back in the US.
As he talks with Kaori, Mick says he didn't steal three clients, only two. Guess what happened with the third one?
Ryo and Kaori have the habit to have their fights at the Cat's Eye. What is Miki and Umibozu's reaction? To jump in an underground refuge, with Umibozu using his ears to note what Kaori is breaking on Ryo's head to add it to their tab.
A chapter cover has a well-drawn picture of Kaori... Wearing mallet earrings.
The cover of the chapter where Miki and Umibozu decide to marry: super deformed style, with Umibozu dressed as a groom with an head bigger than the rest of his body and Miki dressed as a bride over his head.
She first meets Ryo when he gets mistaken for a Panty Thief (for once he was innocent: a box of lingerie being brought in a shop fell before him, and he was looking at it when the shop personnel saw him), so Miyuki saved him... And promptly billed him for the help. Ryo has no cash with him, so she says he'd pay her with his body... And Ryo does what you expect him to do.
Later Ryo takes down two hitmen gunning for her, so she says they're even... Only for the escape.
Upon learning he's City Hunter, Miyuki hires Ryo... And gets in an epic negotiation battle with Kaori. That includes detractions for Ryo touching her.
One of Miyuki's job: helping an old man robbing the usurer who ruined him. The hold-up is rather pathetic, and works only because Ryo helps him...
Ryo and Kaori's reaction to Miyuki revealing they're transporting nitroglycerin for a mad prospector.
Then they have to ask her if she has ever transported more dangerous things. Her answer: radioactive wastes to dispose. That and how she disposed of it: she left it before a police station.
Miyuki insists to sleep alone, without Kaori there to defend her, and ready to demand being protected for free if Ryo jumps on her. Kaori's solution? A transparent bulletproof and soundproof box under the opening of Ryo's secret passage to the guest room, and locking the passage as soon as Ryo is in the box.
The criminals were after Miyuki because a now defunct client of her gave her informations on drug trafficking routes to deliver to the FBI, and hid them in a song. Upon learning the destined recipient for the song, Miyuki agrees to record the song and have Saeko deliver it... But her singing is so bad that Ryo compares it to the cry of a beast having her throat being cut. Thankfully the code was in the words...
How did the arc end? Miyuki trying to hire Kaori as her permanent partner.