Orlando Baxter is a stand-up guy in a couple of meanings of the term.
Baxter the Worcester stand-up comedian returned to South High Community School (in its new Apricot Street building) on March 19 to film a YouTube comedy special. Baxter was a student at South High and later taught there.
“Orlando Baxter: Live From South High” is both a loving tribute to the teachers and students who helped influence his life as well as a funny series of anecdotes about growing up and returning to be a teacher South High.
“This school really saved my life,” Baxter said. “It was the first time I was at a school where it felt the teachers cared about me as a person.”
“Orlando Baxter: Live From South High” (just over 55 minutes in length) is free on YouTube. The accompanying digital album “Laughs From South High” is available on most streaming platforms. There are links to both at orlandobaxter.com.
As Baxter relates in the special, he was originally kind of a shy kid from Great Brook Valley who wore thick, bifocal glasses.
His father was a non-presence while his mother struggled with drugs for a while. So Baxter and his brothers moved in with his aunt and uncle in the Beacon Street/Main South area. He started going to South High Community School because that was the designated school for the part of the city of Worcester he was now living in.
It proved to be fortunate.
“There were a number of teachers at South that had a major influence on me. I don’t know where I would be without that. I just knew in that environment I would end up doing well,” Baxter said. “My sense of humor started coming out a bit more. My confidence.”
Baxter graduated from the school and went on to be a student at the College of the Holy Cross.
He was a teacher at South High for two years before following his own advice to students to pursue their dreams by deciding to take the chance to become a stand-up comedian full time. He’s now a fan favorite at festivals, colleges, on late night TV and social media. His DryBar comedy special “Glorified Baby Sitter” has over five million views on YouTube and five million views on Facebook, and he also co-wrote and co-starred in the feature film “Salesmen” now streaming on Amazon.
“I had a lot of fun when I was teaching,” Baxter tells the audience in “Live From South High.” But there were “a lot of things I didn’t like” about the job, he adds. “I didn’t like the lockdown drill.” Baxter says that he got into trouble over one lockdown drill when the assistant principal didn’t see him with the children in the corner of a classroom as the teacher is supposed to be. Baxter had to explain that he used to be in the corner. “I’ll get in the corner first.”
At a fire drill Baxter also got into hot water with administration as a teacher when the alarm went off and “I left the room first.”
The stories drew constantly laughter from the audience during the special.
The audience included “teachers, people that wanted to watch the show, a lot of friends I went to high school with, a lot of students I taught,” Baxter said during a recent interview.
“This was full circle of my life. Some had never seen me perform. A lot of them didn’t know my background.”
Baxter said that during the height of the pandemic he was doing Zoom shows for different schools and he put on a 30-minute show for the teachers at South High. That led to the idea of a comedy special live at the school.
“Live From South High” is self-produced.
Most comedians have an aspiration to do a comedy special, “but usually you’re waiting for something like Netflix,” Baxter said. “I felt that I wanted to tell my story. I figured I had a pretty good story and a good special — let me produce it. So we shot it ourselves.”
Baxter tells the audience “I thought I’d do something special for teachers.”
With schools now returning to in-class teaching following lockdowns, a lot of teachers are “driving to work hoping the building’s on fire,” he says to laughter.
While the thick glasses could be a magnet for bullies, the young Baxter discovered that as a counter he had a “a talent for making people laugh.”
In the special he says that he was born with a cross eye and could never take the glasses off or else someone would invariably say, “‘Who the hell you looking at?’ ”
Baxter liked sports, but during a Little League game when he was playing right field “the ball hit me in the face.” He had “one eye looking at the short stop, the other at the concession stand.”
Noting that he grew up in the 1980s, he said he got some bad adult advice about how to deal with bullies. One uncle suggested, “pick up a brick and bust their head open.”
Baxter gets cheers when he says he grew up “in a beautiful neighborhood called Great Brook Valley.”
But he acknowledges that he had trouble understanding the name. “There’s no real brook, there’s no valley. There’s a creek that flows when you … in it.”
Baxter said there were “issues in my house … my father was really good at hide and seek.”
At Christmas when his mother could not afford a Christmas tree, she tacked up lights on the wall in the outline of one. That was OK, but then she also outlined presents. “This isn’t cool!” he says he told his mother. “You need to get off the drugs!” He tells the audience he loves his mother to death, and she’s many years sober now, but for a while she had problems with addiction and spent a spell in prison.
That led to the move to Main South and going to South High.
After graduating from Holy Cross, Baxter tried the corporate world for a while, but didn’t like it.
So he checked in with a former mentor at South High, Gerald Creamer, who was now in charge of an alternative school in the Worcester Public School system.
Creamer asked him to teach math at the school for a couple of months, and was undaunted when Baxter said he was no good at the subject.
Baxter launched what would become a 12-year teaching career. “It can’t be too bad,” he told himself about teaching math temporarily.
However, “I forgot how kids were when they walked in a room and saw that they had a sub. Those kids were on me … ‘You ain’t no real teacher cuz if you were you wouldn’t be crying.'”
Baxter taught at the alternative school, Claremont Academy, Sullivan Middle School and spent the final two years of his teaching career at South High, where he was the in-school suspension teacher.
The stories about some of the students he had in suspension such as one boy who made cat noises and another who misunderstood what his previous teacher had meant when he was asked to “crack the window” are among the funniest in the special.
They were “amazing kids” and he “got a lot of jokes,” Baxter says in the special.
On a more serious note, school violence also comes up during the special. Baxter says, “Breaking up fights, they don’t give you no training,” which is a prelude to an almost surreal anecdote.
As for arming teachers, Baxter says that financial inequalities would likely find any school he was teaching at giving him a musket.
Toward the end of his time at South High, Baxter’s comedy career was showing promising signs. Much or his material has been related to teaching, as in “Live From South High.”
“I was already well into teaching. I started doing stand-up as something I wanted to do. It just grew. The highs and lows, I fell in love with the challenge of it,” Baxter said.
Eventually, he began to “think I could do it professionally, based on the number of things I had to turn down … but it’s still a huge fear.”
In the special he recalls how one student challenged Baxter. “‘You always say you’ve got to follow your dreams — how many people think Mr. Baxter’s being a hypocrite?'” the student asked.
Baxter reflected, “Man, the kid’s kind of right. I’m doing it (comedy) but not really doing it.”
He gave himself “five years to pursue comedy … The kid said, ‘I’m proud of you.'”
Baxter has been a full-time comedian now for several years, including the pandemic years.
“My career’s been going great,” he said. “I’ve been doing late night TV … Different countries (including the Edinburgh Fringe Festival in Scotland), a movie. I’m very happy to be where I’m at. Just to be able to do something I enjoy for a living .”
The pandemic “did shut down everything, but there was an opportunity to do Zoom shows,” Baxter said. “Zoom comedy is terrible. It’s not the same feeling. But it’s better than nothing.”
Baxter still lives in Worcester, but with the pandemic lockdowns a thing of the past, at least for now, “I’m barely home, always on the road for the most part. Clubs, cruise ships, colleges,” he said.
He was being interviewed after just completing an engagement on a cruise ship and coming back to Worcester for a few days.
Does he miss his old teaching job?
“I wouldn’t say the job necessarily. I think the opportunity to connect with students,” Baxter said.
“Just being a Black male from Main South I knew that meant a lot to a lot of the kids. They felt comfortable talking with me. I miss that. Not the job necessarily, but I do miss the students. It was a very stressful job. I don’t miss the stress on the job.”
Meanwhile, besides returning to South High as a comedian, he’s also been known to show up at school events such graduations when he can. “I’ve always had a relationship with South,” he said.
One of Baxter’s new ventures will see him rekindling school days for others.
In the upcoming podcast series, “Because of You,” he said he’ll bring on guests to reconnect with their teachers.
“Because of You” is expected to launch in late August. People can watch for updates at orlandobaxter.com.