New York City’s high-stakes high school admissions process is taking center stage in a new off-Broadway production.

School Pictures, running through Dec. 3 at Playwrights Horizons theater, draws on playwright Milo Cramer’s experience as a tutor, which often entailed preparing kids for the Specialized High School Admissions Test that determines entry to eight coveted public schools.

Through a series of musical vignettes, all performed by Cramer over ukulele and piano with a lone teacher’s desk in the background, the play offers a portrait — by turns funny, wrenching, and hopeful — of kids navigating academic stress, social pressure, and parental expectations.

While the SHSAT looms large, Cramer’s students also grapple with classroom challenges and applications to other competitive public and private schools.

There’s the aspiring actress whose dad pushes her to dredge up a traumatic incident to craft a better response to an admissions essay prompt about overcoming adversity; the accomplished preteen student-athlete struggling to write an introductory email to a would-be high school coach; the student so anxious about climate change she can’t bring herself to study.

The show also traces Cramer’s evolving understanding of New York City’s inequitable education system, and takes a brief detour into former Mayor Bill de Blasio’s breakfast habits.

Chalkbeat spoke with Cramer, who uses the pronouns they/them, about their experience tutoring, how the show came together, and what they learned about education in New York City.

This interview has been lightly edited for length and clarity.

The show draws on your experience as a tutor for New York City kids. Can you give an overview of what your job was as a tutor, and how that came to be the basis for the show?

I was a tutor for three different companies at different times, which was so interesting, because you travel all over the city. You’re often at people’s homes, but sometimes you go to schools and meet kids in schools. Every one is just so vastly different. You knock on the door, you never know what you’re gonna get.

There’s some very monied environments where there’s pressure. There’s some very monied environments where there’s not pressure, because you’re kind of a servant, and you don’t even meet the parents. And then there’s also contexts where it feels like this is an investment the family decided to do, it’s a significant budget line for them, perhaps, and there’s real hope that you’ll have an impact.

The kids themselves range from children to adolescents, to teenagers. And basically what always happens is, for the student, there’s deep emotional problems, which are often the result of circumstances or family problems.

So we’re working on some assignment, which can feel arbitrary or goofy, or insanely important, like, ‘learn about the Civil War,’ but you only had an hour, my job is at stake, and I need to do a good job. But then also you want to help this child who seems like they are not speaking because they’re so depressed about the world.

It just brought up all of these questions for me when I started doing it. I was so unqualified, and I felt like a fraud. And it was immediately existential.

The show traces your own understanding of the education system in New York and your role in it. What did you come to learn about education in New York City and the role you were playing in it as a tutor?

I’m not a parent, so sometimes I feel like I’m throwing stones because I haven’t gone through the lived experience of having a child and loving your child and wanting the best for your child. But what’s actually best for your child is a humane and just universe. And the New York City school system does not seem so humane or so just. And it’s also dizzyingly complex.

Really what I was doing, people wanted to get into the eight specialized public high schools. And so mostly I was tutoring the specialized high school admissions test to eighth graders hoping to get in, which was very lucrative. And it’s also adorable because you meet sweetheart [kids] and help them do reading. But it’s complicated, because in some ways the test is a segregation mechanism. It’s such a complex thing. It means different things to different communities and families. So I’m hesitant to make sweeping statements.

In the play, I tried to just provide facts, and then provide really detailed stories that are specific and poignant. And to not editorialize so much, because I’m not an expert.

Why did you decide to specifically highlight the Specialized High School Admissions Test? And what role did that test play in the lives of the students who you work with?

It’s mainly what I tutored, the SHSAT. What’s funny is I used to serve Bill de Blasio breakfast every morning as a barista. And there was a moment where [the SHSAT] was in the news a lot. What’s funny is that now, because I’ve been working on the show for six years, it feels like a period piece. It feels like it’s like this time capsule.

Parents are often really stressed out [about the SHSAT]. And they really determine the family culture. And so often it loomed large for them. And for students, it’s like OK this is another test, another hoop I have to jump through, I really want to go play Minecraft. Some students are anxious about it, because they sense that it’s important, but there’s just so much you don’t understand when you’re told.

One really interesting framework that I learned from one of my tutoring companies was: There’s students who are moving with the world, students who are moving away from the world, and students who are moving against the world. That just seems true to me. And all three of those are wonderful ways to be. But they are different from: Are you good at math and reading comprehension?

A number of the students you worked with were in middle school, and a lot of what comes up in the show is just what it means to be going through that time of life. So what did you learn or relearn about what it’s like in middle school?

It seems very brutal. Especially if you are a girl, it seems brutal, although boys are learning a lot of weird things, too.

One thing is in major media high school shows, teenagers are so sexy, and so powerful, and have so much freedom. And in real life, adolescents, their days are full. A lot of them were just very overscheduled. In a way you are trapped inside different adult-managed spaces. The world is about completing homework assignments on time.

So the biggest thing I found myself coaching was something I need help with, which is just normal executive functioning. Like, I have to send an email, I have to send it by noon. And then I also have to remember to pack lunch. That is so hard, I think, for a lot of adults, just basic, consistent, healthy behavior.

There are some really heartbreaking moments of parents kind of adding to the stress that their kids are experiencing, but also some very touching moments about them being there for their kids and helping relieve that stress. I’m curious through all that, how you came to think about the parents of the students you worked with.

I remember when I was a freshman in college, my impulse from high school was to stay up until I finished my homework. And then I was dating a person who was like, ‘Well, it’s 10 p.m., we have to go to bed.’ And I was like, ‘We haven’t finished our homework.’

They were prioritizing health, self care. We didn’t have that word then. But I think that’s just interesting, those are two different types of people, somebody who’s gonna go to bed no matter what when it’s time to because that’s important, and the person who is going to stay up, even if it’s unhealthy and crazy and a product of bad time management to get it done. Both are good and bad.

And I would see that in different families. People just have such different relationships to money to work, to ambition, and to school. There’s academic success and failure, wealth or not wealth, if you’re driven or not, if you value process or product, it’s so infinite, the complexity of human stuff.

Being a tutor I just had so many fascinating windows into these different kinds of case studies. Parents often want what’s best for their kids, but it can be too intense.

Michael Elsen-Rooney is a reporter for Chalkbeat New York, covering NYC public schools. Contact Michael at