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Meet the brilliant, warped minds of Boston comedy who are teaching your children by day


Nearly every comedy club offers classes to teach people how to be funny, or at least how to do stand-up. Most are taught by accomplished, seasoned industry veterans; still, there’s another whole side to the intersection of humor and pedagogy.

A lot of comedians, it turns out, are also teachers. Like, real school teachers. With classes and stuff. You may wonder, like I did, if they’re moonlighting as comics, but really it just makes a lot of sense however you slice it. Both gigs require that a person stands in front of crowds of people, and if they do their job correctly, the audience is supposed to remember what they heard for a lifetime.

In speaking with these nine teacher-comedians, I myself learned quite a bit, like that they’re all in some sense hoping for a gym instructor slot to open up. In the meantime, here are some of Boston’s most hilarious educators explaining what it’s like to be a student of comedy in their own classrooms.

 

How long have you been/were you a teacher? (Why did you stop?)

I was a teacher for seven years in Worcester Public Schools. I started to get burnt out with long nights and early mornings.

 

Why did you get into teaching?

I needed a job after school because being a theater major wasn’t bringing home the bacon, so I started subbing, then got hired full time.

 

What subject did you teach?

English, theater, college preparation.

 

What subject would you have liked to have taught?

I lucked out and got to teach what I wanted.

 

What’s the worst thing a student ever said to you?

I got punched in the back of the head once to move me out of the way so he could punch the kid in front of me.

 

Was there ever a time a kid said something that was so funny to you, but you had to hold back from laughing in their face?

Yeah, everyday. One time I had a toothpaste stain on my tie and a kid came up to me and said, “Mister, you have cum on your tie.”

 

In 15 words or less, describe your feelings toward standardized testing.

Fuck. That. Noise.

 

What is the worst thing one of your fellow teachers got caught doing?

I didn’t witness it, but one teacher brought two kids out to the football field to fight.

 

What was your proudest moment as a teacher?

I have thank-you notes and letters from my students after plays, I still read them sometimes after I bomb onstage.

 

How long have you been/were you a teacher? (Why did you stop?)

I was a teacher for the Cambridge Public Schools for five years. I was at the Morse School for three and C-Port for two. Until I got fired for hitting a kid with a (hockey) stick.

 

Why did you get into teaching?

I got into teaching because I’d already been a personal trainer and aerobics instructor for a few years before I went back to school. I assumed if I could teach mostly white professional women how to move their bodies and be happy with the body they were given, now called body positivity, I could definitely work with kids.

 

What subject did you teach?

I taught PE, the best subject ever, after art. I taught when the majority of children could still run around without getting winded.

 

What’s the worst thing a student ever said to you?

“Miss Stirling, I don’t need to read. I’m going to be a professional basketball player and my lawyer will do all that shit.”

 

What’s the worst “…you can use that” you’ve gotten from another teacher in regard to jokes?

I wasn’t doing stand-up when I was teaching, but I always made the other teachers laugh whenever possible. Their jobs were so much more tedious than mine. I didn’t have to administer those stupid tests every three months.

 

What was your proudest moment as a teacher?
When I had almost the entire school riding whatever had wheels around the Charles River past Harvard without anyone getting hurt. I didn’t check to see if I were allowed to have them off school grounds, no insurance, no nothing. And it was fucking awesome!

 

Is there anything else about being a teacher and a comedian you would like to mention?

I love performing, being in front of an audience, whether it’s a room full of 5-year-olds or 15-year-olds.

 

How long have you been/were you a teacher? (Why did you stop?)

Twelve years full time, two years part time. Eventually quit to pursue stand-up.

 

Why did you get into teaching?

The classroom is a stage, and I was always good at working with kids. Easy job.

 

What subject did you teach?

I was a youth development mentor, which combined social work and after-school instruction.

 

What subject would you have liked to have taught?

I would have loved to teach gym.

 

What’s the worst thing a student ever said to you?

“This is your job?”

 

Was there ever a time a kid said something that was so funny to you, but you had to hold back from laughing in their face?

Often students would say something off the cuff and I’d have to go in the hallway to laugh uncontrollably.

 

If or when a student finds out that you do stand-up comedy, what’s the first thing that goes through your mind? How do the students react?

I had an old student who found my clips on YouTube and I had to have a talk with him. Basically about how I was following my dream to be a comedian and I hoped he understood what that meant so I could keep it private. I assumed he told everyone, but he never did and I was appreciative.

 

Have any of your student’s parents come to see you do stand-up?

I frequently had parents at many shows when I was starting out.

 

What’s the worst “…you can use that” you’ve gotten from another teacher in regard to jokes?

“You should use this in your act” when a girl wiped dog doo on my pants after she stepped in it. I did.

 

How long have you been/were you a teacher? (Why did you stop?)

Twelve years, stopped to pursue comedy full time.

 

Why did you get into teaching?

I really enjoy summer vacations.

 

What subject did you teach?

TV production, math, and history. I was also an in-school suspension teacher.

 

What subject would you have liked to have taught?

Physical education.

 

What’s the worst thing a student ever said to you?

“You ain’t no real teacher!”

 

If or when a student finds out that you do stand-up comedy, what’s the first thing that goes through your mind? How do the students react?

I hope they don’t ask me to tell them a joke. “Mister, tell me a joke.”

 

Is there anything else about being a teacher and a comedian you would like to mention?

Stand-up comedy is hard but teaching is harder. They need to be paid more money.

 

 

How long have you been/were you a teacher? (Why did you stop?)

I have been a teacher on and off since 1992. I have taught everything from first grade, to special ed, to high school English. I currently teach eighth-grade math. … mostly for the sympathy … and the summers off.

 

Why did you get into teaching?

I went into teaching because I didn’t like being in advertising right after college and wanted to do something “nice.” I came from a family of civil servants, so it was pretty natural although I originally resisted it—my siblings are firefighters, social workers, and teachers. I have the chance to positively impact the lives of 110 kids every day—and that’s pretty cool.

 

What subject would you have liked to have taught?

I would teach anything—except science.

 

What’s the worst thing a student ever said to you?

Kids swear a lot these days when they think you can’t hear them. But I have dog ears when it comes to swears. Luckily it isn’t usually about or to me.

 

Was there ever a time a kid said something that was so funny to you, but you had to hold back from laughing in their face?

I am usually the one accidentally saying ridiculous things in class—and hoping that the kids don’t catch it. I write jokes about it. True story: Once I tried to tell a kid that I had already done my due diligence with detention duty, and accidentally said “dildo” and not once, but like 18 times in a Porky Pig nightmare: “I’ve already done my dildo, dill-do, dildo, dil-dammit,” and the kids just laughed and laughed. Do eighth-graders know what a dildo is? I just found out what one was last year. … best Yankee swap ever.

 

If or when a student finds out that you do stand-up comedy, what’s the first thing that goes through your mind? How do the students react?

I don’t tell the kids I do comedy, but they find out. I have some sets online that I didn’t put up, and I use that as an example of how dangerous and permanent the internet can be. Luckily I am just talking about adult topics, but no swears! Kids seem to like the idea that I do it—it’s novel for them if nothing else.

 

What was your proudest moment as a teacher?

Whenever I see a kid understand a concept or feel better about themselves as a student and gain confidence. Once at a graduation ceremony a student came up to me, gave me a big hug and told me that I “had turned his math frown upside down.”

 

How long have you been/were you a teacher? (Why did you stop?)

I’m still currently teaching. This is my eighth year, high school English.

 

Why did you get into teaching?

I wanted something more fulfilling than what I’d been doing. I’ve always enjoyed working with kids, and since I’m horrible at saving money, I figured having a pension would be smart.

 

What subject did you teach?

High school English.

 

What subject would you have liked to have taught?

PE! Those are the smartest people on the planet.

 

What’s the worst thing a student ever said to you?

A kid accusing me of telling him to jump out of the window and commit suicide.

 

Was there ever a time a kid said something that was so funny to you, but you had to hold back from laughing in their face?

Nah, they’re mostly not that funny.

 

If or when a student finds out that you do stand-up comedy, what’s the first thing that goes through your mind?

I tell my students all the time, and they ask if I talk about them. I say yes, because I do.

 

In 15 words or less, describe your feelings toward standardized testing.

It’s impossible to condense the essay I want to write about it into just 15 words, sorry. It is the fucking worst.

 

What was your proudest moment as a teacher?

Getting a girl on stage last year to do comedy—she did three different sets throughout the year.

 

Is there anything else about being a teacher and a comedian you would like to mention?

It blows having to keep my social media private. I’d definitely get fired.

 

How long have you been/were you a teacher? (Why did you stop?)

I started off teaching at my local library and then got hired by New York’s most popular language center—the one with all the “Learn English” ads on the buses and subway. From there I taught in San Jose, Costa Rica; Santa Monica, California; helped open and taught at a new center at Eastern Kentucky University; and most recently got a teaching gig to settle here in Boston.

 

Why did you get into teaching?

I was broke [as fuck] just outta college, furthering my debt with overpriced vodka sodas in New York city bars, nightclubs, and at countless open mics.

 

What subject do you teach?

I teach English to international students from all over the world who are mostly in their 20s and want to go to university in the States. I also lead stand-up comedy writing workshops for many hilarious and increasingly funny students.

 

What’s the worst thing a student ever said to you?

A student once told the class that she “had fun at the Holocaust.” She was from Brazil and pronounced her R’s like H’s. She meant that she had fun on the roller coaster.

 

Was there ever a time a kid said something that was so funny to you, but you had to hold back from laughing in their face?

One kid was fed up with phones going off in classes. He said, “Why can’t everyone just make their phone a vibrator? Everyone should have a vibrator!” He did have a solid point! I suggested that he Google “vibrator” later.

 

If or when a student finds out that you do stand-up comedy, what’s the first thing that goes through your mind? How do the students react?

I first think, “Great! More audience!” and then I think, “Nevermind … They don’t understand English. I gotta be a better teacher!” The students usually giggle a little, some are astounded, and some actually look me up on YouTube. Then at least if they don’t get me, I can blame it on language and culture!

 

In 15 words or less, describe your feelings toward standardized testing.

Standard.

 

What is the worst thing one of your fellow teachers got caught doing?

One teacher I used to work with copied the final exam and gave it to his students to practice before the test. He’s no longer at my company.

 

What was your proudest moment as a teacher?

I taught a course called “Global Citizen” with content created by the Peace Corps and afterwards two of my Japanese students planned a trip to volunteer at an orphanage in Uganda.

 

How long have you been/were you a teacher? (Why did you stop?)

I have been teaching for 21 years. If I quit by the time this goes to print, it means I’ve hit the lottery. Or I have been whisked away to China on a government mission due to my ability to say hi and order beer in Mandarin.

 

Why did you get into teaching?

Mostly because of my dad. He taught for 22 years. When he retired, they just handed me his overhead projector and gave me a set of keys. All kidding aside, I started out coaching (which is teaching). … I had taught part time one year and I had liked it. So I got a job at a private school, St John’s in Shrewsbury. After a year a job opened up at my old high school (a year after my father retired). I have been slinging history and psychology ever since.

 

What subject would you have liked to have taught?

Physical Education. Hands down.

 

What’s the worst thing a student ever said to you?

“I know where you live.” That student never stepped foot in my class again.

 

Was there ever a time a kid said something that was so funny to you, but you had to hold back from laughing in their face?
Kids were talking about the movie American Pie, and a girl says, “You know what’s weird is that band camp is not actually very wild. You know what’s really crazy?” She adds, “Church camp!”

 

If or when a student finds out that you do stand-up comedy, what’s the first thing that goes through your mind? How do the students react?

Usual student reaction: Student: “Can you do some comedy for us?” Me: “If I haven’t made you laugh by the end of the year you can have your money back.”

 

What’s the worst “…you can use that” you’ve gotten from another teacher in regard to jokes?

“You could talk about our staff meetings, they are a comedy sketch right there.”

 

What is the worst thing one of your fellow teachers got caught doing?

I really love my job. People sometimes steal and people sometimes violate a trust that has been placed in them. These two things get people fired in every racket, but these are the two most heinous acts of which an educator can be guilty.

 

What was your proudest moment as a teacher?

When I see former students and learn what they have been doing. Especially the alumni who have returned as faculty.

 

Is there anything else about being a teacher and a comedian you would like to mention?

I feel lucky to work in two fields where I experience very satisfying moments. There are frustrating and disappointing moments in each for sure, but that only makes me appreciate the peak experiences all the more when they happen.

 

How long have you been/were you a teacher? (Why did you stop?)

This is weird for me to answer. I’ve been working with kids/teaching consistently for about nine years, but I taught karate and music sporadically before that. If I had to guess, probably about 13 years in total.

 

Why did you get into teaching?

Honestly, childcare jobs were just available to me when I graduated college. I had started at summer camps, and it was just easy for me to continue on after summer. That and I seemed to have a knack for it.

 

What subject do you teach?

So I mainly work in after-school programs, which can be all over the map. But I also taught preschool and subbed in kindergarten. And, as I said above, karate and music. I’ve also taught stand-up to adults.

 

What’s the worst thing a student ever said to you?

They normally don’t say anything mean to me. If they do, they’re not trying to hurt me. Like, they’ll come up to me and say, “You got a big belly,” or, “Why don’t you buy a new car? Can’t you afford one?” When I first started a new job in a tough city, one kid looked at me on the first day and said, “I give you three weeks.” I was there for three years and outlasted that kid. Also I’ve been punched in the face.

 

Was there ever a time a kid said something that was so funny to you, but you had to hold back from laughing in their face?

Literally every day. Like, every single day. The other day, a kid forgot the word uvula and said vulva instead. I have a bit about a particularly funny and poignant thing a kid said to me.

 

If or when a student finds out that you do stand-up comedy, what’s the first thing that goes through your mind? How do the students react?

My first thought is usually, “Please don’t Google my name.” Luckily they wouldn’t be able to find my stuff online.

 

What was your proudest moment as a teacher?

One kid, who was really difficult, became a straight-A honor student the year after I worked with her. A couple of kids I’ve worked with became staff members at my program, which is pretty cool. … One of the most emotionally affecting things I see on a regular basis: I work with a lot of kids who have experienced a lot of trauma. Almost all of my children live in perpetual poverty and are children of color and are affected by all of what comes with that. I’ve worked with special needs kids, homeless children, children who’ve been abused physically and/or sexually, and children who have parents that get incredibly sick or die or have been murdered. And one of the most impressive things I see is child resilience.

 

Is there anything else about being a teacher and a comedian you would like to mention?

I think teachers make good comedians for these following reasons: Teaching involves a delicate mixture of performance and empathy. You have to be able to feel the energy of the room, and conduct it to where you want it to go. Sometimes you bomb. People think that both teaching and comedy are about talking, but they’re equally about listening, and about responding to the emotions in the room.


This article was produced by the Boston Institute for Nonprofit Journalism and published in DigBoston.


Dennis is a rabble rousing subversive jocular misanthrope that will make you laugh or gasp. He covers comedy.


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