Anthony Zonfrelli


Investment Analyst 




“The conclusion I always come to is this: the people that came out tonight wanted to see a comedy show, probably to get away from whatever it is that's happening, so our job is to transport them to a world where nothing's wrong, and they're safe to laugh.”




By Abigail Bliss

While many millennial in the gig economy hold down jobs that complement each other, at least thematically speaking, Anthony Zonfrelli, investment analyst and comedian, divides his time between two drastically contrasting gigs. Working in a cubicle during the day and on stages across Boston and Cambridge by night, Zonfrelli straddles the worlds of real estate and real talk, devoting his down time to making people laugh, in the era of Trump and political circus.

Zonfrelli dabbles in sketch comedy, stand-up, and improv. There’s no comedy form he won’t try, and there’s no topic he won’t touch. In fact, he argues that some of the best comedy comes on the heels of tragedy and that traditionally taboo topics can be comedic in the right hands. With Late Night talk show hosts catering to immense and growing audiences and with traditional forms of journalism under attack, comedians like Zonfrelli are uniquely poised to offer commentary on American politics and society at this moment in time. I recently sat down with Zonfrelli on a rainy Saturday morning to ask, ‘Are comedians the truth-tellers of the modern era?’

Could you tell us about your day job?

I am an investment analyst for a commercial real estate investment company. I work in a cubicle on Excel all day. Basically, the bosses buy and sell office buildings, and I help them run the analysis on new buildings on the market and help them determine if they'll be profitable.

And, what is your side hustle?

My side hustle is comedy in all forms.

Those seem very different. Do they overlap in any unexpected ways?

There’s no immediate crossover that I can think of, though the soft skills you get from performing do help you in just about everything. If anything, the only real common denominator between the two is the willingness to put in the work.

How did you get into comedy?

I had always wanted to do it. I have a picture from when I was in kindergarten [pulls out phone]. The assignment was, ‘What do you want to be when you grow up?’ and I drew comedian. For a long time, I wasn't able to do it because I was always too busy with school, sports every season, and music pursuits, but in my senior year of college, I finally joined a standup group – the Harvard College Standup Comedy Society.

I performed for the first time, after three years of hemming and hawing over it, and I did very well in front of all my peers at school. Then, I went to an open mic in Cambridge the next week, which I now know is a pretty notoriously difficult mic to do. I went up and I bombed. I knew that I wanted to keep doing comedy because after I went up and killed in front of my college friends, I walked off the stage and felt like, ‘I can't wait to do this again.’ And, after I got off stage bombing in front of a bunch of other comics – real comics – in the city… I thought, ‘I can't wait to do this again.’ Having the same reaction to both outcomes was a sign to me that it was something that I should keep doing.

You said you do comedy ‘in all forms.’ What are they?

Standup is one. That's how I got started. I’ve done that for probably two or so years, and I'm still doing that now.

At one point, I did a standup show at Improv Boston in Central Square, and I was intrigued enough to take an improv class, which I'd always wanted to do. I hadn’t gotten into the improv groups in college that I auditioned for because I was horribly unfunny at that point. I’ve now taken all the class levels and I'm currently doing a handful of different improv projects.

Sketch is another form that I do. My senior year in college, I joined the student run sketch show called Sketch at Harvard, then I didn't do it again for probably two or so years. I joined a Disney-themed sketch show, then I auditioned for a group called Terrible People at Improv Boston, which is called that for a reason, and I was cast as an actor/writer in that group. We perform monthly and it's one of my favorite projects in which to perform.

What inspires your standup? Are there any topics you won’t touch?

As far as inspiration for my material, it's just whatever weird thoughts my brain comes up with. When I first started, I would do silly, dark one-liners because that came to me easily while writing. That was what felt comfortable, but I realized I could never actually talk about things that were happening to me in real life because I was just doing a character, and it was all obnoxiously fictional. I had this huge transformation two years in, when I actually started to write all new material in a completely different style. I wrote to the church that I went to in college, and I said, ‘Would you guys mind if I headlined a benefit show that you guys sponsor?’ and my pastor said, ‘Sure.’

Sounds like an unlikely venue.

Yeah, we put on a benefit show for members of the church and the proceeds went to a middle school in Cambridge. It was a great time, and it motivated me to write all new clean material, which shaped my writing from that point forward.

I have a pretty overactive brain, and there's nothing I won't joke about if I can make it funny enough. I think there are ways to joke about things that are taboo or morbid, as they’re portrayed in the right light. The joke shouldn't be taking advantage of the victim of any situation. If anything, it should highlight the absurdity or ridiculousness of the tragedy.

That's a hard line to walk.

Jeselnik was one of the comedic inspirations for my dark one-liners, but I wouldn't go as far as he would in jokes. For instance, he pushes the offensiveness, and I would just hover in the dark territory. He pushes more boundaries than I would.

Comedians have long played a truth-telling role – in everything from Shakespeare to Late Night TV. What role do you see comedy playing in American society today?

I think comedy can play that role of truth teller, whether or not the comic intends to. Look at Hannibal Buress with the whole Bill Cosby incident – he wasn't intending to be a whistle blower, but he sparked the whole nationwide story, and that wouldn't have happened if it weren’t done in an art form like Hannibal Buress'.

However, I also think that comedians play the role of relief. Whenever there's a national tragedy, and we all have a show that night, all the performers are in the green room beforehand saying, ‘Should we address it? Should we talk about what happened with the audience?’ The conclusion I always come to is this: the people that came out tonight wanted to see a comedy show, probably to get away from whatever it is that's happening, so our job is to transport them to a world where nothing's wrong, and they're safe to laugh.

Do you see any similarities between politicians and comedians, both performers in their own right?

You're right. I guess the strategy for appealing to a large number of people is the biggest connection in my mind, and enough people go about them using the same tactics. Some people will just completely focus their identity, or on what they think will appeal most to the audience. Some people will say, ‘Forget pandering. I'm just going to tell the truth. I'm going to do what I want.’ I think it's almost safer to be a comic; audiences are a lot more forgiving of who you are as a person in this profession.

I'm looking forward to the moment when female comedians aren’t expected to perform material strictly related to their gender. Any comedians currently pushing those boundaries?

I recently saw two female specials that I absolutely loved. First, Sarah Silverman's most recent special. It was fantastic. It was better than most of her previous ones and didn’t conform to the hokey female comic stereotype that's imposed on a lot of female comedians. And, then the special by Garfunkel and Oates was really, really good. The premise of their special was that they were raising money for their special, and at no point were you filtering their comedy through their gender. Also, Tig Notaro. Tig is great.

I think it's not entirely the responsibility of female comedians to change that way of thinking. This is a weird place for me to talk from, as a young, privileged, white male, but I think that it's up to the rest of the standup community to change that perspective on female comics. A big part of the problem is that we're still referring to them as female comics, drawing attention to them as female comics when they're introduced, or just booking a female comic on a show for the sake of having a female on the show. People doing these things might think they're helpful, but they're also kind of perpetuating the problem.

How has comedy changed under Trump?

There are a lot of hack jokes. I tend to steer clear of political comedy because it's so polarizing. A lot of people are turned off as soon as you pick a side, and I don't want to alienate half of the audience immediately. Granted, I perform in Cambridge most of the time, so it's not that big of a problem for me, but there was a while when, at least in this little bubble, everyone was terrified. I went to Improv Boston on the Wednesday night right after Trump was elected, and it seemed like everyone in the city was depressed. Some of my friends performing that night were contemplating quitting comedy, as silly as that sounds, and then they went out and had one of the best shows that they had ever put on. The crowd absolutely loved it. It was like, for a while, everyone was in this place where we were all going to be okay.

That said, I know some other people have lost their interest because it seems like so many more important things are happening now, and comedy can seem so trivial. I went the other route; I think it's more important now than ever.

What’s unique about the Boston/Cambridge comedy scene? How does it differ from other cities?

Boston's a weird place. It's weirdly progressive, but also super archaically traditional. There are certain topics where you can be really liberal, and there are also certain topics where you cannot.

Which are those?

Again, a weird place for me to talking from, but the topic of race is brought up a lot in Boston. That doesn't really affect me, per se, because I don't get very political in my comedy. If anything, I'll just draw attention to the fact that Boston is weirdly divided. Cambridge crowds are very smart. They'll get a lot of jokes that I tell that won't necessarily work in other places, and the comic needs to be aware of that.

Do you have a go-to joke that works with every crowd?

Yeah, I'd say it's one of my favorite jokes to do now. It starts off with me voicing a very controversial opinion: I claim that sex is overrated and then compare it to cookies.

Do you ever get heckled?

Rarely, and when I am, I try to include it in my performance. I've never gone to combat with an audience member. I think that's probably a result of my style now, where I’m just trying to be friends with everybody.

Who are your favorite comedic voices?

It’s funny because these three all came up in the same time from the same city: Pete Holmes, John Mulaney and Kyle Kinane. They're all fantastic. I try to incorporate some of Mulaney's writing style in my writing because I think he's the most technically fantastic standup. I resonate most with Pete Holmes; I love his energy and his doofiness, which I try to capture. I like that he has a good time on stage. One problem that I run into in this city is that I also enjoy myself on stage, and I don't think other comics enjoy seeing that because we're supposed to be miserable. It's kind of an unspoken rule that with which I completely disagree.

What did you think of Dave Chappelle's recent Netflix special?

I watched both of them. I thought the one in Texas was much funnier than the one in LA. He focused more on his dealings with racial issues, and he did it so skillfully. The one in LA, while it had its moments, I can't say I was surprised by how archaic some of his opinions were. When you've achieved the level of Dave Chappelle, though, you can get away with whatever you want. He had been all but retired as a hermit for the last ten years, so, of course, he's going be a little bit behind on some social issues. As long as he's making people laugh, which is his job, and he gets paid, like, $20 million a special, who am I to tell him what he should or shouldn't say?

He was pretty transparent about his motivation for doing the specials – that $60 million. Focusing a bit closer to home, which local comedy venue should people check out?

I love performing at the Comedy Studio and Improv Boston. Those are my two home bases. The Comedy Studio is one of the best comedy clubs on the East Coast. It's in the attic of a Chinese restaurant. It's dingy. It's how comedy's supposed to be. At Improv Boston, there's a lot of really good experimental comedy. People are taking risks there all the time that pay off incredibly, and it's one of the most welcoming communities I've ever known.