Mr. Oozora: Tyrannical parent who unforgivably abuses Hibari, or loving, but old fashioned father who cares deeply about his ‘son’ and treats her rather fairly by the standards of the time?
Hibari: Romantic trans girl determined to make her One True Love see that they're meant to be together, or Jerkass who sexually harasses Kousaku?
Also, while the canon Hibari thinks of herself as a girl (as best as she understands it for the era she lives in), some fans prefer to think of her as Wholesome Cross Dresser instead.
Kousaku: A stubborn, abrasive yet ultimately caring dork who clearly loves Hibari or a complete Jerkass who Hibari only really tolerates because she's in love with him?
Heartwarming in Hindsight: For a series that centers around Hibari and Kousaku's relationship, it becomes this when their VAs Satomi Majima (Hibari) and Tohru Furuya (Kousaku) began their own relationship during the anime's run and eventually marry a year later after its conclusion.
LGBT Fanbase: While some of its presentation of gay and gender non-conforming persons could be considered problematic and/or Fair for Its Day today, Hibari-kun! is nonetheless especially popular with these audiences because of its iconic gender-bending protagonist.
When Kousaku and Tsubame think of what might happen to Hibari if the truth about her gets out, they imagine her decapitated head hung up next to a sign warning that this is the fate of "perverts" like her. It's a creepy scene even without taking the dead Hibari's expression into consideration.
Kaji's BSOD when Tsubame and Hibari play a rather mean prank on him, which goes all the way into literal psychosis. Granted that he recovers, it's still unsettling to see him go clinically insane, even if only for a short time.
Spiritual Predecessor: Finds a thematic relative every decade, despite the closer ones being more otokonoko oriented. The 2000s has Prunus Girl, and the 2010s has Trap Heroine.
At one time when Hibari is teasing him, her father gets so angry with her that he rips down a samurai sword from the wall and has to be physically restrained by his daughters from killing her, shouting that he will put an end to Hibari for her insolence. Although this is Played for Laughs (and also out of character for the elder Oozora, who is at most other times shown to actually care a lot about even his least liked child), it probably comes across as less funny than in the 1980s to at least some viewers today, when violence against LGBT folks is even more frowned upon.
A number of the series' jokes about yakuza, underage drinking and some other topics would be harder to get into a TV anime nowadays, as compared to the 1980s.
In an American context as of 2021, some of Eguchi's depictions of non-Japanese characters would probably be considered racist by some. It also happens that some of the cast appears in blackface (which is not as widely understood as offensive in Asian countries like Japan) as an In-Universe joke.
Values Resonance: Though it's a gag manga that features a lot of what would now be considered casual homophobia and transphobia in America, as typical for the 1980s, Hibari's character has only become better received with time. Despite her family's general disapproval, she isn't ashamed of passing as a girl or crushing on boys. The fact that most characters who display homophobia/transphobia get frequently punished and humiliated certainly helps.
