Milo Cramer’s ‘School Pictures’: A Memoir-Musical on NYC School Choice at Cherry Lane

Milo Cramer’s one-person musical School Pictures is currently playing at the Cherry Lane Theatre in Manhattan’s West Village, where the show shifts halfway through from short, tuneful songs about his former tutoring students into a lecture on New York City school choice, the Specialized High Schools Admissions Test and wealth inequality, Vulture reported. Cramer, a former tutor, performs the memoirish show himself, accompanying each number on a ukulele, a tiny piano and a keyboard.

The Lecture That Interrupts the Songs

Cramer argues that the Specialized High Schools Admissions Test is racist and that wealth inequality affects every aspect of education in the city. Midway through the performance, he stops singing to deliver this lecture, calling himself a “cog in the fucked-up machine.” He says he did not intend to enter a political “conversation” with the show. “I don’t know how to fix the system,” he says. “Neither does Zohran.”

Cramer Crafts Songs from Tutoring Struggles

The show originated when Cramer was working as a tutor and held a commission from Playwrights Horizons. He was 27 at the time, nervous, and writing what he calls bad scenes, so he sent his director, Morgan Green, therapeutic songs he had written for himself and asked if they could become a show. During the pandemic, he let himself write the songs as a “rock-star fantasy.” An education journalist then galvanized and structured the piece; Cramer and Green also sent drafts of the lecture to Alex Zimmerman at Chalkbeat, who told them when the argument “doesn’t quite follow.” After a 2023 run at Playwrights Horizons, Vulture critic Sara Holdren named School Pictures her No. 1 show of the year.

Ukulele Defies Musical Gatekeepers

Cramer describes his onstage persona as complicated, aiming for sincere, deadpan and normal rather than cutesy or stylized, though he changes the approach each night. The production has evolved from its Philadelphia premiere, which featured a big yellow set and an infantilized, “Blues Clues”-style version of the character, to the simple staging at Cherry Lane. He says he once struggled with pitch. He defends the ukulele as “the best instrument,” arguing that it facilitates communal music-making and counters the gatekeeping he experienced from church choirs, guitarists and music teachers. The show has drawn two negative reviews: one in The New York Times called it twee, and an NYU sophomore wrote that Cramer seemed like a “white middle-aged teacher, desperate to be cool.” Cramer says he and Green studied with Joanne Akalaitis and Daniel Fish at Bard, where they encountered an austere stagecraft tradition he tries to emulate with warmth instead of alienating coolness.

Cherry Lane, Dior and the “Cooler” Venue

The West Village theater is owned by A24 and operates in association with the restaurant Wild Cherry, making it one of New York’s “cooler” venues; Phoebe Bridgers filmed a performance there directed by Lance Oppenheim, and Dior held a party there during Fashion Week. The show’s program lists “Presented by Dior,” which Cramer notes with amusement given that he is performing an earnest show about anti-racism. He says the venue asks which influencers to invite, but he cannot name any.

Cramer on Memoir, Money and Fixing the System

Cramer says he is financially insecure and anxious about money, not knowing what his next gig will be. He notes that the songs in School Pictures have solid hooks, unlike what he sees as the lack of melody in productions such as Maybe Happy Ending. A fan of Taylor Swift, he calls Red her best album. He is not in touch with the students who inspired the songs; their names and genders are changed and the material is collaged out of respect, creating what he calls a sleight of hand between truth claim and fiction. His earlier play, Cute Activist, ran at the Bushwick Starr. He praised a New York Times article by Nikole Hannah-Jones on navigating the school system. “The goal is to destroy cool forever with a laser beam of pathos,” he says.