How Stephen Sondheim’s Work Did (and Didn’t) Translate to the Screen

What is it that makes it so difficult to adapt Sondheim to the screen? There aren’t, with very few exceptions, great screen interpretations of his work that aren’t filmed theater productions.

He gives you something that you think you understand. Even with “Into the Woods” (the 2014 film), it’s like, “Oh, it’s a deconstruction of fairy tales.” But that’s really not enough to go on. There’s something really profound going on there about sadness and loneliness that is probably really hard to square with the genre trappings. They’re tricky because he’s always doing two things at once. And when you make a film, filmmakers often focus on the spectacle, not realizing that the spectacle has to be elided. That’s really hard to do in film.

I was thinking today about which Sondheim works I wish there were movies of. I never want “Sunday in the Park With George” to be a movie, just by virtue of what it is, how it’s produced, what it’s about. What it’s doing feels so New York stage, it would be so strange.

Could you talk about Sondheim and Madonna’s cinematic work in “Dick Tracy”?

For me, as a little gay boy with his Madonna “I’m Breathless” cassette tape in 1990, it was the essential thing. Period. “Dick Tracy,” the gruff lantern-jawed masculine comic book detective, just does not interest me. But I remember those songs. It’s one of those things that’s a queering agent. “Dick Tracy” really feels like a hybrid of a lot of different sensibilities. I like the way that Sondheim and Madonna’s contributions help to negate the uber-masculinity of the text.

And we have to talk about “The Last of Sheila” (1973), which he co-wrote with Anthony Perkins.

That’s a tricky one. It’s interesting that they chose an intricate, whodunit murder mystery plot, because how else would you intelligently funnel this Sondheim complexity and idea of overlapping narratives, characters, themes into a genre film? I think that’s what makes it delightful. With Sondheim you see the gears working without it taking you out of the film. It’s a movie about game playing, in which you’re constantly being asked to size up the people involved. It’s very mechanical in a fun way.

And in a nasty way that I love, too.

One of the game cards in the film reads, “You are a homosexual.” And the way they talk about it is surprisingly casual and sort of progressive. There’s the idea that this is an accusation. But when it’s revealed, there’s a real casualness about it. It’s surprising for “closeted” — at the time — gay men to write.

See It Big: Sondheim runs through May 1 at the Museum of the Moving Image in Astoria, Queens. For more information, go to

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