Hippie Teacher

Let's get in touch with our inner-granola, m'kay?

"Did I ever tell you kids about the sixties?"

May or may not be a good teacher, but never a good disciplinarian. Often let students call them by their first name ("Mr. Hippie Teacher is my father; you can call me Rod"). Definitely Truth in Television; many people had art teachers like this. While in fiction they can teach any subject, art teachers, guidance counselors and other teachers of "soft" or "creative" subjects tend to predominate with hard sciences being less common unless crossed with Absent-Minded Professor.

Contrast with the Sadist Teacher. Compare Misplaced Kindergarten Teacher and Psychologist Teacher, and Hippie Parents for the parent variant.

Examples of Hippie Teacher include:

Anime and Manga

Although he is too young to be a real hippie, Watanabe Osamu of The Prince of Tennis fits the mold.
Souma from Sora no Manimani. He spent most of his twenties travelling all around the world and working for N.G.Os.

Film

Ms. Tebbit, the drama teacher in Were the World Mine. Although it's implied that she may actually be a fairy in disguise.
Although not exactly a hippie (he's a rock musician), Jack Black's character from School of Rock fits the bill, especially his " stick it to the Man" diatribes and very liberal views on discipline.
Enid's summer school art teacher in Ghost World fits this to a T.
Mr. White in The Last Mimzy.

Literature

Barbara Finney from The Cat Ate My Gymsuit was the first person to help insecure Marcy Lewis break out of her shell. Her controversial teaching methods has also caused an uproar from a large portion of the school faculty.
Although not actually hippieish, Madame Frout, headmistress of the Frout Academy of Learning Through Play in the Thief Of Time, has invented a method of teaching that doesn't involve dicipline because she wasn't any good at it. Her best teacher, Susan Sto Helit, completely ignores it.
Earth Mother (her codename), one of the Magical Arts instructors at Whateley Academy in the Whateley Universe. She was a 'flower power' superheroine in the 60's.
Mr. Freeman, the art teacher from the YA book Speak (although the narrator takes pains to point out that he's not an ineffectual disciplinarian; he has different rules than the other teachers, but he does make people follow them).
The music teacher in Bridge to Terabithia is an older example of this.
Ms Partridge, Bigmac's social worker in the Johnny Maxwell Trilogy used to be like this, before dealing with Bigmac wore her down:

When she'd started the job, less than a year ago, she'd firmly believed that everything that was wrong with the world was the fault of Big Business and the Government. She believed even more firmly now that it was all the fault of Bigmac.

Live-Action TV

iCarly: Mr. Henning. He loves nature, disproves of modern methods (or rather just major energy wasting ones), and takes students on a root and berry retreat.

Spencer: You know, when I was at Ridgeway, I had a teacher who was such a loser! He's a freaky weirdo and smells like rotten wood...
Mr. Henning: Spencer? That's me.
Spencer: What? (pauses) Oh.

- Henning seems to use the root and berry retreat as a form of Cool and Unusual Punishment on his students. While he himself enjoys it, he knows his students don't and uses it as a threat to make them try their best on their projects (failing grades can only be made up by going on the trip with him).
Another one of Schneider's shows, Victorious, has Mr. Sikowitz. He's a very good, but very laid-back teacher who Does Not Like Shoes.
Mr. Rosso on Freaks and Geeks is a Hippie Guidance Counselor.
- Interestingly enough, while he still fits the classic trope, he's also a well-rounded enough character to be legitimately helpful at times and be thoroughly capable of discipline.

Rosso(driving up to Lindsay and Daniel who are skipping school): Guess who's in trouble!

Art Cooney on The Wedge.
Mr. Jellineck from Strangers with Candy, in sharp contrast to his secret lover.
- According to Paul Dinello, Jellineck (a totally insecure loser) was based on Hippie Teachers who in real life are often considered kind of creepy by their students, who don't really want a forty-year-old man giving them advice on problems he shouldn't even know about and insisting that he "gets" them all the time.
Ms. Dawes of Degrassi is this, she is the art teacher. She also happens to LARP in her spare time.
Mr. Donovan of Square Pegs, who dressed conservatively but would hark back to his nostalgic days of sit-ins and experimental theater.
J.D. becomes a bit like this in Scrubs: Med School. "Let's gather round the Teaching Tree!"
Valerie on Awkward, who is more of a Cloudcuckoolander than a hippie, but fits the mold by being a horrible disciplinarian and treating the kids (especially Jenna, her favorite) like they're her friends.

Video Games

Professor Potsdam in Magical Diary: Horse Hall, although she can be terrifyingly competent when the need calls for it. All while calling you and the other students such things as "starshines" and various diminuitives for plant and animal offsprings.

Web Comics

Merlin Ambrosius, in his role as Arthur's art teacher in Arthur, King of Time and Space ... maybe. He's definitely a hippy and a teacher, but we don't really see him teach to judge if he actually fits the trope.

Western Animation

Mr. Van Driessen on Beavis and Butthead (pictured). Supposedly based on a real teacher Mike Judge had in high school.
- Mr. Mackey, the school counselor on South Park, is almost a Captain Ersatz for Mr. Van Driesen, since he is constantly using the catchphrase "Mmmkay?" He doesn't quite fit the profile visually with his suit and tie and short haircut, but he is a lot more "empathetic" toward the children than teacher Mr. Garrison (who often loses his temper when the students get unruly).
Mr. O' Neill on Daria, who is scarily similar to Mr. Van Driessen save for the fact that he's not overtly a hippie. When Daria and Jane come to visit his apartment in one episode, it's filled with new age-y paraphernalia, and he offers them tea with a gem tincture.
Mr. Simmons in Hey Arnold!.
Recess: Ms. Grotke is the most obvious example, but according to The Movie, Principal Prickly and Ms. Finster were Hippie Teachers back in the sixties.
Mr. Burkenbake on The Fairly OddParents, literally a Hippie Teacher. Also Mrs. Sunshine in "No Substitute for Crazy" until Timmy wishes her into Mr Crocker's job, and she reveals herself to be a scarily competent Fairy Hunter whose professional name is Miss Doombringer.
- Mr. Burkenbake. Niiiiceeee.
Doug's school counselor straddles this and Misplaced Kindergarten Teacher. As that he is always suggesting "Hugs" and other "Make Love" solutions to problems, his office is plastered with feel-good posters, and he looks vaguely like a caricature of Bob Dylan in an ugly sweater.
Mr. Mandrill from My Gym Partner's a Monkey, another hippie school counselor.
Hank Hill has locked horns with his share of Hippie Teachers over the years.
Miracle from Sit Down, Shut Up.
Springfield Elementary has one—he's just a background character, but he usually shows up when there's a group of teachers onscreen. When all the textbooks were stolen and the teachers had to improvise their lessons, he sat cross-legged on his desk and asked, "Did I ever tell you kids about the '60s?"
- Skinner dates one in a recent episode.
In The Replacements episode "Cheer Pressure", Riley replaces the cheerleading coach with a hippie teacher. Hilarity Ensues.

Real Life

Truth in Television: Being a hippie is essentially a prerequisite for a professorship at The Evergreen State College, an "alternative" institute of higher learning in Olympia, WA, which does away with, among other things, grades.