(Average+) Stop!! Hibari-kun!

Series in one sentence:
The only thing that makes Hibari "a freak" is the fact she has Japanese parents, yet blonde hair and blue eyes.

Series in more sentences:
Kōsaku loses his mother, and as there's no family to take him in, goes under the care of an old friend of hers. But his new family appears to be connected to the mob, and the girl he gets a crush on is soon revealed to be the boss' son.

Kōsaku isn't sure on how to treat him, while Hibari has already returned the crush and imagines a future with him.

I came across this anime through a randomly suggested Youtube video that more or less proclaimed this show was good trans representation. I'd like to talk about that bold statement later, but first the show itself, as I very much doubt it it was ever meant to represent anything.

"Stop, Hibari-kun!" the intro song shouts at you, but the odd thing is that the majority of episodes don't star Hibari or her quest of swooning Kōsaku, or her family's quest of turning her back into a boy.
Hibari is like a selfish, overpowered, perverted Bugs Bunny, and the episodes vary between basic and outrageously strange. The last episode is about Hibari obtaining physic powers, because why give your show a proper close, am I right.

 

Having that said, this anime is a comedy and nothing else. A very early 80s comedy, filled to the brim with questionable scenes and awkward jokes.
Honestly, many of the episodes were a chore to sit through, I did not enjoy myself. I just wanted to see Kōsaku and Hibari interact; I wanted to see what the intro song promised me, but the few scenes you think qualify as character development lead to nothing.

Kōsaku was a boring character, in appearance and behaviour. I wouldn't be able to give him a description if I tried.
I don't know what made Hibari prefer him over the millions of other guys who wanted to date her, I don't recall getting an explanation for it. Maybe it's the sole fact Kōsaku would be told/was told the secret she's a boy, since he's officially a member of the family, and so she'd have no reason to hide anything from him. That's not a great reason if so, though.

Now, as for the "trans representation" claim some people entertain..

..The answer is no. Not gud representation.

 
Anime and manga creators have long been into the concept of designing flawless girls and dubbing them "a boy, actually", and Hibari is one of them.
She's really only male on paper and it doesn't look like the show wants to acknowledge she's a boy. With that I mean: Her family constantly mentions it, but as a cartoon character, she possesses every classic female feature an artist can give an unsuspicious girl character. Prominent eyelashes, a feminine voice, a tight waste, not an ounce of the muscle structure a teenage boy would have at this stage of his life, and there's a complete absence of male genitalia whenever she's seen walking around in undergarment, tight shorts, or leotards.
Even Kōsaku has a bit of a hump going on when you see him in his underwear, and lewd jokes and bare breasts appear multiple times in the series, so it's not like the show was animated by prudes.

So then, if Hibari has the luck of looking female without the help of drugs and surgery, how can there be people who consider her proper trans representation?
If 95% of the series isn't even about Hibari's transsexuality, how can there be people who consider her proper trans representation?

She might as well be a biological girl. There are no struggles to relate to; she comfortably wears revealing clothes, because she has the body to pull those off, and there are maybe only two short instances in the entirety of the series that brushes the issues a trans person might recognize.
Realistically speaking, Hibari would've been found out by her school long ago, if only because she keeps making use of the girls' locker room and wears those Japanese lady shorts during gym time. That's not something the common person with baggage down below can pull off without people noticing, but the show doesn't even dare to suggest this fact.

If her gender is such a non-factor, why even make it a feature? The show might as well be about the daughter of a ruthless mob boss, who acts overly delicate and cutesy, yet is a powerhouse underneath. 

 

In short, "Stop!! Hibari-kun!" starts out interesting, but stops caring about its own premise after only a few episodes, and before too long, you're watching a giant monkey fist fighting a fucking giant crab, bee, and marshmallow-faced armadillo in the ocean.