Interview: Orlando Baxter brings it full circle in ‘Live From South High’

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It’s a feeling held by the majority that once you graduate high school, the last thing you want to do is walk through those doors ever again. Well, in the case of Orlando Baxter recording a new special, there was no other way to make it happen then to do just that.

With his debut full-hour comedy special, Live From South High, which premiered on YouTube on May 6, Baxter not only revisits his academic roots by recording the set in the spotlight of the auditorium of his old stomping grounds (as both a student and a teacher), but also by showing love for the people who helped him get to that spot. With heartfelt jokes and stories of hardship, growth, and navigating his way through the oddities and attitudes of his students during his teaching days, the Worcester native pays homage to the city that helped raise him in a myriad of ways, from the setting and the music, to his less-than-glowing reflections on Great Brook Valley, all the while showing his unbridled support and appreciation for his former colleagues in the process.

We had the chance to chat with Baxter about the special, as well as what it took to change things up on the fly, trying something new, navigating through the emotions that come along with baring your soul in front of a hyper-hometown crowd, and so much more.

Class is in session. Check it out.

Jason Greenough: The best place I think we could start, naturally, is your new special, Live From South High. How does it feel to have this special come out?

Orlando Baxter: There’s a lot of emotions, man. I’m excited, and overwhelmed a little bit with doing all these interviews, but overall, I’m excited and overwhelmed in a positive way. Also, I’m a little fearful, because it’s a very personal story and while I think there’s certainly some elements of traditional stand-up to it, it’s mostly storytelling with an arc, and it has something of a Fringe feel to it. So, I’m curious to see how people receive it.

In that regard, obviously these stories come from the moment that the story happened, and you’ve built them up over time. When the whole idea of doing this kind of special centering around these experiences came to you, was it immediately the thought that you’d deliver it with more storytelling than just jokes?

To be honest with you, the intention was originally supposed to be a thirty-minute set about teaching. I decided to change it last minute, because with the amount of people that were calling me and telling me they were going to the show, it was a weird situation. I’ve had shows where I’ve had family and friends show up, but this was like a class reunion, teacher reunion, and family reunion all wrapped into one, and the one thing I realized a few hours before the show was that I had all these people together in one room who know me from different parts of my life, and they might know me from South [High School], but they don’t know why I have so much love for it, and this is the best time for me to do it.

I was thinking to myself, ‘well, we have two shows,’ so I could do the first show how I wanted to do it, which felt more natural to me, and then if it doesn’t go well on the first one, I’ll focus more on the bits for the second show. But once we got to the day, I was just blown away by that moment. I felt that it made sense to share my background a little bit in a comedic way, and also tell some stories about my life so that people could walk away that night saying ‘I knew him, but I didn’t know him, and I know I feel like i do know him a little bit more.’

What gave me the confidence to do it that way was having done Edinburgh [Fringe Festival] twice, where you aren’t as focused on the laughs as you are on the story. So, I felt like I could shift between the two and mesh the two types together. It was the first time that I did it like that, and I feel like it worked out.

If memory serves me, I remember you telling the ‘teacher told me to crack a window’ story at the Boston Comedy Festival a few years ago. With that timeline in mind, and at the risk of being cheeky, does it feel like a sort of graduation for these stories by doing them this way after building them up for the last few years?

Yes, that’s actually the perfect word for it. It’s almost more like a retirement, where I can now move forward and focus on the other material I have that a lot of people don’t know about. It also felt like an introduction of myself to people that may not know anything about me. Doing it the way I did it puts everything in context. When I did Conan, or my Dry Bar special, I could pick and choose the bits I wanted to do, and that would send people away laughing, but it didn’t fully give people a sense of who I was. I think this is the first set I’ve ever done where it felt like my proudest set. I really feel like people will be able to walk away from this and know who I am a lot more than they did in those other situations.

You touched on it a little bit just now, but after 17 years of doing stand-up, and doing everything from late-night sets to international arts festivals, how does it feel to just now have that sense of really introducing yourself, or perhaps like you’re just getting started?

A part of it makes me feel great, because I finally got the opportunity to do it, and having self-produced it and putting it out there on my own, I ‘m not waiting anymore, and that feels good. If I had looked at it seventeen years ago, I probably would’ve thought that was just way too long to be introducing myself and it may have turned me away. Not really though, because I just look back at these seventeen years of experiences, growing pains and sacrifices I’ve made, and it was all worth it. 

When I did Conan, it took me a long time, but I was able to do it after always wanting to, and since I started doing stand-up, I wanted to do a special that I was proud of. It’s more than just the jokes. I’m actually proud of what i did here, even if people don’t view it as many times i would like, I do feel like if they ever do go back to it and watch it, I think they’ll enjoy it, but also walk away feeling like they know me better. That in itself is an accomplishment for me.


As it should be. I’m pumped to see the reception this gets, because even thinking back to that night of the recording, it felt like a special night from the jump.

I agree with you, man. The other thing I like about it is that if I had just gone up there and did solely teacher-centered material, I feel like people would think it was only for teachers to watch. But I do think a lot of people can walk away from watching this special with something else, even if it’s from a stand-up perspective and it gives them the confidence to do more storytelling, or slow their pace down or allow themselves to be more vulnerable onstage, or whatever it might do. Some people will watch it and love it for the teacher material, and others will like it for the storytelling aspect, or it might even make someone think about reaching out to an old teacher they had to let them know how much they appreciated them.

I feel like I got to do a lot of cool things with this one special. How often do you get to tell a teacher you had that they had a huge impact on you, and that you appreciate them and love them for what they did for you? It was just great, and it was great that I got to do it at my old high school. Too many things, bro.

I can imagine. There are so many aspects at play here. Obviously, it’s your old school. Your old principal is there, and your old teachers. They’re all there, but it’s also Worcester, and at the root of it, you being onstage is just the continuation of the last story you tell. How did you process that and navigate through those emotions to stay focused on the mission of delivering the special?

To be honest, I don’t even know. We also didn’t mention how my mother was in the crowd that night, as well, and it wasn’t like i was telling all funny stories. Some of them were real-life difficult situations, and I don’t know how I did it, but I knew that the moment was bigger than whatever I thought it was going to be originally, and I just had to roll with that feeling. Worst case scenario was that I had a second show, and that was my attitude. I remember talking to [Directors] Luke [Jarvis] and Rob [Pooley], and telling them that I was going to do something different that night, and explaining to them that I was just going to let it roll and that I just needed them to rock with me on it. 

It was just a gut feeling. I had a conversation with Corey Rodrigues about two hours before the show, and I was telling what I was feeling and thinking. I told him that I thought it was bigger than I had thought it would be, and he gave me the confirmation of ‘just roll with it.’ He made it make sense, and said ‘if it doesn’t go well, you always have the second show.’ That was the push I needed to follow my gut.

Man, Corey is just such a positive force, huh? Just a super supportive dude for the scene. I love that story.

Absolutely. Like a young Morgan Freeman. [laughs]

Obviously the basis of this special is your experiences as a teacher, and you had done the virtual teacher appreciation shows over the course of the pandemic. But what was the spark that really made you want to make it into an event like this?

Sometimes, you do things not realizing that there’s a big picture playing out. You just haven’t seen it yet. Doing the Zoom shows was something to do to keep me busy, and it felt like something that could be helpful for teachers, and I’ve always had that in me because I love teachers and I was also one myself for a long time. 

I know teachers appreciate comedy, but the spark for me was doing the movie [Salesmen]. We were doing the movie, and at the end of the shoot, we started discussing promotion and how we were going to market it and everything, and Rob and Luke told us that if we needed anything else, or wanted to work together again, to just let them know. Something in me, at that moment, was just telling me I should shoot a special. Sometimes you gotta just listen and pay attention. 

They had never shot a special before, but they seemed excited about it, and I knew I had material to do it. That same week, I just so happened to talk to the principal at South High, and he was telling me about how morale is low and stress is high at the school. He asked me if I wanted to do another show for them, because I had already done a Zoom show for them at the school, and it sounded like a good idea. That got me thinking that we should take all of those signs and put them all together, and literally within a couple months, that’s how it all came together. Just like the material that night, it was impulsive but it just felt right.

Going back to the last story in the special, where you tell yourself you’re going to give it five years to do comedy. At this point in your career, if you had the chance to sit down with “2005 Orlando,” and told him that the next 17 years are going to be “blank,” what do you think you’d tell him?

I would tell myself to write down as much as possible, because you’re gonna need it.

I think with comedy, especially in the beginning, you’re in this mindset that it’s all about the comedy. You’re not really thinking about how difficult the road can be. I have done well, and I may not be where I want to be yet, where there’s a whole lot of comedians in front of me, but I’m very happy with what I’ve done so far because I’ve always progressed. Just like with teaching, I was always getting better and had situations that gave me confirmation to keep going forward. I’ve sacrificed a lot, so the words I would say wouldn’t be so much about the stand-up aspect, but rather what you give up personally. That would be the thing that would’ve made me more hesitant.

But man, since I left teaching, I’ve been able to work with some incredible people and see cool places, and have so many cool moments. I’m not some no-name anymore, but that doesn’t mean I’m not enjoying my life and time as a comic, and what I’ve been able to do so far.

That’s what matters most, right? As cheesy as it might sound, the passion and enjoyment you have in comedy is obvious, especially with this special. Now, having done both comedy and teaching, what would some parallels that you can take or have taken from teaching that you could apply to the stage?

I always say that teaching gave me the confidence to stand up and talk in front of people. Before I was teaching, that was one of my biggest fears, but once I started teaching, I also started getting used to the idea of standing up and talking, and maybe even throwing out a joke here and there to kids that did not care at all, which means I also got used to bombing. So I think that was helpful.

It also taught me how to be cautious of the people in the audience. When you teach, you can’t really use profanity. I mean, you can, but it’s a risk, so you have to learn how to speak in a certain manner, which helps me in terms of working clean. I mean, this set was PG-13 at most, but it was still fairly clean. I love that teaching gave me that ability to get up on stage and not have to swear. There’s nothing wrong with that, but I like that I can switch back and forth.

As a teacher, you just get better the more you do it, and get used to routines, and that’s very similar to comedians. Like with lesson plans, sometimes jokes work and other times they don’t go how you want them to, and then you gotta learn to adapt and craft your material in a way that an audience can understand it, just as a teacher has to do with their students sitting in front of them.

The best thing you can do is to learn from past experiences and use them to your advantage later, and this special is nothing if not about learning from past experiences and embracing them. In that regard, at the end of this special, what are you hoping is the one takeaway that they get from this new hour full of Orlando Baxter?

I really hope that people watch it, enjoy the comedy, and then want to see more of what I do. This is something I’m actually really proud of, and not just because it’s a culmination of all this time. I just feel really proud of it, and I know some people who have seen me in other situations will notice how I’m doing more storytelling, but that’s just a result of me going to those Fringe festivals. If I hadn’t done those, I don’t think my mind would’ve been able to deliver a set like this.