For some reason in fiction, the school principal is seen as the most likable guy in the school. Could it be that the position of high authority has granted them wisdom and understanding of the plights of adolescents, or is it because he doesn't have to actually deal with the little brats directly day-in and day-out? You decide!
Compare Badass Teacher, Cool Teacher, and Psychologist Teacher as similar, but lower in the system's hierarchy. Contrast with Dean Bitterman. Put those two characters together, and you can have a Captain Smooth and Sergeant Rough dynamic.
See also Benevolent Boss.
- Headmistress Miranda Holbrooke from Little Witch Academia (2017) (next to Professor Ursula) is the most reasonable staff member of Luna Nova, supporting Akko's desire to learn magic without giving her a hard time and dealing out stern but fair punishments whenever they are needed.
- Shinigami-Sama/Lord Death from Soul Eater is the immortal Grim Reaper and founder of Shibusen (or Death Weapon Meister Academy as it is called in the English dub), having created it to defend the world against witches and corrupt, evil souls. Originally a terrifying figure, Shinigami-sama altered his appearance and personality to be more child-friendly, turning himself into The Wonka. He is respected and beloved by everyone in the organization, his image and name plastered all over Death City and is even looked upon as a symbol of worship to some.
- Nezu, the principal of My Hero Academia's UA Academy. He's an affable Reasonable Authority Figure who genuinely has the students' growth and well-being as a priority. (He does have a "darker side" that is played for laughs, though.)
- Professor Xavier from the X-Men comics has long been seen as the wisest and most peaceful of the mutants, which makes him well suited to run a school for the betterment of mutant teenagers.
- Hermione genuinely becomes one of Dumbledore's closest friends in The Parselmouth of Gryffindor.
- My Little Pony: Equestria Girls:
- Principal Celestia and Vice-Principal Luna are just as caring, friendly and loving as their Pony counterparts.
- Dean Cadance is gentle, caring and loved by pretty much everyone, and as said in "Dance Magic", she replaces Cinch as principal of Crystal Prep.
- Professor Albus Dumbledore from Harry Potter was the Headmaster of Hogwarts School of Witchcraft and Wizardry for the entirety of Harry Potter's stay there. He has had a long and eventful life in the wizarding world, including defeating infamous Evil Sorcerer Gellert Grindelwald. He is generally well-liked among the forces of good, his approval rating much higher than Cornelius Fudge when he was running for the position of Minister (despite not running himself), is the only person that Lord Voldemort ever feared and is generally accepted as being the Big Good of the series. As Headmaster, he comes off as a bit of a Cloudcuckoolander but is all-around a loved and respected member of the staff.
- iCarly: Principal Franklin is popular with his students, probably because he's one of the few adults in the school who is not a kid-hating sadist.
- In Buffy the Vampire Slayer, Principal Flutie is a bumbling but nice guy. Unfortunately, just after Buffy makes a real connection with him in "The Pack", he is killed and eaten by a group of school bullies possessed by animal spirits. He is replaced by the outright-villainous Principal Snyder.
- In Class, Mr. Armitage is the headteacher of Coal Hill Academy and a pleasant, approachable character. He is gruesomely killed by an alien in "The Coach With the Dragon Tattoo", and replaced with the outright-villainous Dorothea Ames.
- House of Anubis: In the second season, at least, Mr. Sweet was seen as the dorky-but-friendly headmaster. While occasionally dipping into a darker side of his personality, he was determined to make up for his actions in season one by focusing on being a good principal. The students often referred to him as "Sweetie", showing their affection for him.
- Principal Belding, from Saved by the Bell, is very friendly and personable with the student main characters.
- Dumbledore's pretty friendly with the students in A Very Potter Musical when he's not threatening to expel them if they call him Albums.
- In A Very Potter Senior Year, he's one of the few people who cares about Tom Riddle and makes him believe in himself.
- In the DarkMatter2525 video God of the Paradox, Carl Sagan is portrayed as the Principal of God School. When Yahweh tries altering his diploma so that it says "God of Everything" instead of "God of Pastries" despite his major being in Culinary Arts, Sagan allows it, claiming that in order to make an apple pie from scratch, one must first create the universe.
- Professor Ozpin in RWBY, who is looked-up-to by just about every student in the school, and is willing to bend the rules a few times for his students' benefit.
- Erma has Principal Phibes. While the Creepy Cute Stringy-Haired Ghost Girl/Half-Human Hybrid title character unnerves most of the teachers, Phibes is blind, and thus 'Everyone is the same in his eyes'. He means it. - He's a Secret Keeper for a society of Rat Men living underneath the school, and Erma is not the only Half-Human Hybrid to attend his school.
- Principal Goodvibes from The Grim Adventures of Billy & Mandy is the dean of Endsville Elementary. He is generally portrayed as a lame but well-meaning school principal that gives out bad advice to characters that need them and is generally the Butt-Monkey of whatever supernatural outbreak that happens to be going on at the time. He even admits that he had his name changed to Goodvibes legally.
- The Simpsons:
- Dean Peterson from the episode "Homer Goes to College" is laidback and friendly, and used to play bass for The Pretenders. Homer, however, is convinced that he has to be a "crusty old dean" like the ones in the college movies he sees.
- In "Sweet Seymour Skinner's Badassssss Song", after Skinner is fired,Trope Namer Ned Flanders, interim principal of Springfield Elementary, states this trope as his goal at the assembly that announces his appointment. Unfortunately he's too much "pal" and not enough "principal" and he lets the school become a lawless hellhole with his hands-off approach (when Bart gets sent to his office a dozen times a day so he can eat the Reese's Pieces that Ned freely hands over to guests, Ned is more concerned about being a good host than the fact Bart does principal's-office-worthy offenses a dozen times a day).
- Jacob Two-Two: Principal I.M. Greedyguts' twin brother Y.B. Greedyguts looks this way, giving out hot chocolate to students, having heated rooms, and just being an all-round nice guy. It's totally subverted when it turns out he's a Bitch in Sheep's Clothing and is actually worse than his brother, and the nice facade is to trick students and teachers into applying for his school, which is barely a school, but actually a place where people are forced to run on hamster wheels to generate energy.
- Principal Knave from Mixels is overly enthusiastic and kind to his students, to the point of being a pushover.
- Mayor Jones seems to become this in Scooby-Doo! Mystery Incorporated, after Nibiru is defeated and consequently their timeline is rebooted.