To Milo, From Deepali

dear Milo,

you already know this, but School Pictures is my favorite thing you have ever made. 

School Pictures approaches big ideas like they’re toy instruments. the recorder is impossible to ignore! the glockenspiel is tiny, but it has a sharp ring to it. your work is sharp, sharply observed, sharply performed. when your voice goes sharp, there’s an edge. 

I found a hidden meaning in the show the last time I saw it, and I kept it like a secret. it’s just for me, but here it is. School Pictures is about a songwriter who knows they are failing their subject. it’s a triumphant creative failure of the imagination. I’m smiling writing this. 

remember when you played me the first song you ever wrote for the show, which at the time didn’t exist yet? we were at my apartment working on our unproduced, unfinished, unwritten and untitled regency romance novel musical.

you played me the song and asked me what I thought. I thought the song was amazing, and surprising! that song isn’t technically in the show any more! but it’s definitely in there somewhere. maybe my memory was actually an email. 

remember when you asked me if I thought it was okay for you to be writing songs about your students? I was like, why not! easy answer. just change their names! unsatisfying answer.

songwriter to songwriter?

I had a long history of writing songs about people without changing their names or getting their permission. I was the wrong person to ask, and you knew it. but I have thought about this for many years, and I have a better answer! it's okay as long as you're willing to make eye contact. 

songwriter to songwriter, what does a song promise its subject?

The people with urgent stories to tell
don’t have the means to tell them.

The people who have the means to tell stories
don’t have urgent stories to tell. 

- “Charlotte”

there’s something kind of funny about anyone singing this onstage, in front of a beautiful and expensive house. but you know that, and you use it (to use an acting term…)

it's funny, but why? I never want to applaud, I always want to laugh. why is it funny, and how? the answer is your performance. this moment is perverse! in performance, you yell at us and it’s thrilling. it’s thrilling because it’s futile. and it might seem futile, but it’s hopeful. 

School Pictures leaves me with a lot of strong feelings and wild opinions. almost like I'm one of your students with their…"radical dramaturgical ideas." like…potential is violent in nature! ambition is a drug! stories should be exclusively complication and unraveling! songs should always be conversations… 

but what about the subject?

I’m failing him!
I’m friends with him!
I want to be the one who helps him!
Like a real teacher. Like a real teacher!
Like I’m not just some dumb tutor—

- “Jason”

maybe “some” and “dumb” isn’t a totally perfect rhyme? but then again, it is. it complicates the lyric preceding it, and motivates the lyric that follows. a rhyme can do just about anything. but you know that, and you use them wisely. “real” and “teacher” also rhyme. “friends” and “help” also rhyme. 

a metaphor is the sky 

- “Dana”

this is my favorite lyric in School Pictures. it makes me cry sometimes. I think “use your imagination” is the easy answer to almost every impossible question. 

you like to say that I taught you everything you know about songwriting. I’ll happily take some responsibility for your work, but I’m not your teacher. I’ve learned just as much from you about what my songs do, and where I want them to go. 

there is nowhere to arrive

- “Deepali” (Voice message, 2023)

this is my favorite thing you have ever said. I think you should put it in a song. this is a lyric about the joy of failure. triumphant, creative failure. of, for, and by the imagination. 

it has been a joy to watch your rhyme schemes evolve. absolute imperfection. it has been a pleasure to witness your music reach new audiences. when I saw the show the other night, the audience member next to me was delighted, gasping, leaning in close, laughing, and asking me to delight with her. I did, very, very much. I think you should be very, very proud of what you have made. I am. 

love,
Deepali

p.s. here’s the last songwriting class I’ll ever teach you! every perfect song makes a promise to the listener, and then keeps it — or breaks it. I wrote that lesson after watching School Pictures.

Deepali Gupta is a composer, performance artist, and theater practitioner. She makes work in support of Mad liberation. She facilitates the New Georges Jam and serves on the Board of Directors of The Poetry Project. B.A. Brown University; M.F.A. New York University. deepaligupta.net // @deepaligupta Photo by Nico Kiray