A lot of people are happy to collect their diploma, leave their high school, and never look back. Not Boston comic Orlando Baxter. His new special, “Live from South High,” was recorded in March at Worcester’s South High Community School, where he spent three years as a student and two more as a teacher. He’ll release it on his YouTube channel Friday.
Following up his 2020 Dry Bar Comedy special “Glorified Baby Sitter,” Baxter was looking for somewhere to record his next special, and he saw an opportunity to help lift the spirits of teachers coming back to the classroom after a particularly rough year. “Stress was at a pretty all-time high, morale was kind of low, and to put on a comedy show at the school was something the staff needed,” said Baxter. “So it all made sense.”
Originally, Baxter had intended 30 minutes of jokes about teaching. But the day of the show, surrounded by old friends and thinking about his connections to the school where he had enrolled as a 15-year-old sophomore, he began to change his set.
“When I looked at the situation,” he says, “and the opportunity to kind of reveal myself, you know, and let people have some insight into why I have this love for this school, I felt compelled to tell my background, because I think people would appreciate it more.”
The result of that thinking is an intimate, engaging performance. “Live from South High” lets the audience get to know not only the jokesmith who earned millions of views with his Dry Bar special, but a kid who grew up with problems at home, whose teachers put him on a path to success when success wasn’t a guarantee.
In one of the most personal moments of the set, Baxter talks about his mother’s problems with addiction (he notes that she is in the audience). His love for her is clear. One Christmas when the family couldn’t afford a real tree, she tacked up lights on the wall in the outline of one. Little Orlando was fine with that until he woke up in the morning and found she had also outlined presents, he says in the show. “You need to get off the drugs!” he remembers saying. “This is not cool!”
Baxter notes that his mother going to jail was the lowest point in his life. While she was getting clean — for good, he says — he and his brothers went to live with their aunt and uncle and started school at South High. Baxter was a contradiction: a shy kid who liked to play sports and eventually became class president. He wasn’t the class clown, but he did have fun with his friends presenting morning announcements in a comedic format. And in a TV production class, he and his friends made a notorious comedy show called “Your Mother’s Corner.”
“People would watch us do the episodes, and they thought it was hilarious,” says Baxter. “So yeah, it was good. It was probably one of the first times I ever got to show my ability in front of people.”
Don’t count on footage of those shows popping up online: Most of the tapes got recorded over. Baxter says he has one in his possession, and because of the questionable taste of the material, he is keeping it under wraps. “You’re not gonna ever see that thing up on YouTube,” he says. “Ever. But yeah, it was a great time. And between the students and the teachers, I was able to really grow as a person.”
If Baxter was shy among the larger population of the school, he opened up to those close to him. He has kept in touch with a lot of friends from South High, including Ray Semidei, one of Baxter’s cohorts in “Your Mother’s Corner.” “He behaved like one of us crazy kids, but buckled down and did school like a smart kid,” Semidei says. “And it doesn’t surprise me one bit that he went back to teach, especially when he got the opportunity to go back into that TV room. Because that was home.”
Another former classmate, Ken Bath, sat in a large group of Baxter’s old friends at the recording of the special. He said it meant a lot to them to see Baxter doing well, but they had plans if any of his material singled them out. “They were like, ‘He better not say nothing. He better not make fun of us,’ ” says Bath. Baxter used to wear thick glasses and had a lazy eye. “We’ll just tell him, ‘Hey, Orlando, we have your old glasses’ so he’ll leave us alone.”
Baxter went from South High to the College of the Holy Cross in 1994; he was the first in his family to graduate and go to college. In the special, he recounts the story of how he approached one of his old teachers, Gerald Creamer, to talk about how unhappy he was in a corporate job after college. Creamer asked Baxter if he’d like to teach math for a couple of months. “I said, ‘No, man, I’m terrible at math,’ ” Baxter says. “He said, ‘It’s perfect! The kids are terrible, too!’ ”
That led Baxter to a 12-year career in teaching, the last two at South High, where he presided over in-school suspension. That provided a bounty of material for his stand-up, but it was also his launching pad. He was doing comedy as a side gig until a student called him out for not performing full time. Baxter was always telling the kids to chase their dreams, but he wasn’t doing that himself. “I definitely was at the point where I was starting to miss opportunities,” says Baxter. “I couldn’t go on all the auditions. I couldn’t just drive to New York or fly out to LA and try to audition somewhere because teaching was my main priority.”
That student gave Baxter the push he needed. He quit teaching at the end of that school year and went to Edinburgh to perform at the Fringe Festival. Now he’s performed all around the world, and his career is blossoming. He had a turn in the locally produced feature film “Salesmen” earlier this year, in which he starred and had a hand in developing. Pandemic permitting, he tours the country frequently. He’s got a new podcast and Web series coming out later this year.
And even though “Live from South High” is self-produced and Baxter won’t have a known quantity like Dry Bar to help the special reach audiences, he’s confident people will enjoy it when they find it. “Whatever I do next, hopefully, that will lead people to it,” he says. “I think people will walk away from this [and] definitely have a sense of who I am and why I love this school, but also why I have so much love for teachers.”
With Graig Murphy, Chris Dimitrakopoulos, Janet McNamara, and James Dorsey. At Sam Adams Taproom, 60 State St., May 12 at 8 p.m. $15. www.samadamsbostontaproom.com/comedy
Nick A. Zaino III can be reached at firstname.lastname@example.org.