WATCH THE TRAILER

From South High student, to teacher, to comedian—and back to the stage where so much of the story began.

THE STORY BEHIND THE SHOW

Live From South High wasn't originally supposed to be a show.

In 2022, Orlando returned to South High—the school he had once attended as a student and later returned to as a teacher—to record a stand-up set.

But when he looked out at the audience, he saw people from nearly every chapter of his life: former teachers, former coworkers, high school friends, former students, friends and family.

They all knew different pieces of his story. Very few knew the whole thing.

So Orlando put aside the show he had planned and started telling it.

He talked about the teachers at South who changed his life, the unexpected path that eventually led him into teaching, his years in the classroom, why that chapter ended, and the equally unexpected path that led him into stand-up comedy.

What happened that night became Live From South High. 

 Since leaving education, Orlando's comedy career has taken him to Conan and BET, some of the world's most prestigious comedy festivals, and stages across the U.S. and internationally. In 2023, he performed at the 19,000-seat TD Garden as part of Comics Come Home, and his Dry Bar Comedy special has been viewed more than five million times. He has also co-starred in the Amazon Prime feature Salesmen and performs nationally as part of the Bored Teachers Comedy Tour.

But Live From South High brings the journey back to where so much of it began.

WATCH THE SHOW

See Orlando in action from the original Live From South High performance.

MORE THAN A SHOW ABOUT TEACHING

At its core, Live From South High is about more than education.

It's about work, identity, ambition, risk, change and starting over.

Orlando's story happens to begin in a classroom, but the experience of wondering whether the life you've built is still the life you want is something almost everyone can understand.

That's what makes Live From South High a show for educators—and for anyone who's ever found themselves wondering what comes next.

FOR EDUCATORS

Orlando doesn't approach education from the outside looking in.

He lived it.

For 12 years, he worked in public education, experiencing the students, staff, administrators, parents, frustrations, victories and absurd moments that make school life what it is.

The result is comedy that educators recognize immediately — without feeling like they're sitting through another professional-development session.

It's a chance for educators to laugh together, recognize themselves in the stories, and leave the work at the door for a night.

WHAT PEOPLE SAID ABOUT THE ORIGINAL SHOW

Live From South High was originally performed at South High in March 2022. Here are a few reactions from people who experienced the show firsthand.

“Your performance had us laughing from start to finish.”

“Your performance had us laughing from start to finish. It was amazing how all the educators could relate to your stories and put themselves in your place. You are a great example of how someone can take the very serious job of education and approach situations with a smile and a chuckle.”

— Gerald Creamer, former coach, teacher & principal

“The most honest, real, and funny assessment of education.”

“Your show was the most honest, real, and funny assessment of education. Anyone who has entered a school could relate. Best night out in a long time! Thank you!”

— Katie, Worcester, MA

“Cried through the entire show…”

“Cried through the entire show — I was laughing so hard. Orlando lifts spirits with his truly hilarious stories! Always fresh and engaging.”

— Lisa Bolshaw, South High

“As a teacher, I could relate…”

“As a teacher, I could relate to so much of his material. He truly has a gift to make people smile!”

— Whitney, Worcester

“Non-stop laughs and relatable anecdotes…”

“If you're looking for non-stop laughs and relatable anecdotes, this is it. We've all been students and have teachers in our lives, even if we aren't teachers ourselves. We laughed until we cried.”

— Christy Rutland

“Hilarious, relatable, and touching…”

“Great show from start to finish! Hilarious, relatable, and touching stories. Well done!!”

— Dan, Worcester

BRING your school to LIVE FROM SOUTH HIGH 

When Live From South High comes to your area, Class Ambassadors help spread the word at their schools and bring coworkers together for a night of comedy.

We'll provide everything you need to share the show.

You make the connection. We'll take it from there.

BECOME A CLASS AMBASSADOR
 

BOOK LIVE FROM SOUTH HIGH

Bring Orlando Baxter's one-man show to your school, district, educator conference, organization or special event.

[BOOK LIVE FROM SOUTH HIGH]