The Adventures of Hilary Knight and Lena Dunham

An hour before I was scheduled to speak to Hilary Knight last week, the illustrator who co-created the famous fictional character Eloise, I received a note that he was about to send me something that would warm my heart. Next thing I knew, in my inbox there was a PDF of the holiday card Knight had sent around this past December, starring his assistant’s two-year-old daughter dressed as Eloise; meanwhile, Knight posed as Santa. The girl had the same last name as mine, although there was no relation. “A willing stand-in for ELOISE!!” he wrote.

Indeed, I was charmed. And any fan of the mischievous little girl Eloise, who lived in the Plaza hotel, might feel the same about Knight, who is the subject of a new HBO documentary, It’s Me, Hilary: The Man Who Drew Eloise. The film, which explores Knight’s childhood, career, and life, was produced by Girls creator Lena Dunham, who famously has an Eloise “tramp stamp” on her lower back. “I read an interview early in her career in which she talked about her Eloise tattoo, so I sent her some books,” Knight said. “She immediately responded, and we had this series of interviews. Each time she came dressed up in a different costume—the first time, she was all in pink. It reminded me of Björk and her swan dress.” Initially, Dunham planned to write a story about Knight, but quickly decided that it was more interesting to make a documentary. “It started immediately,” Knight said. “Just like Eloise.”

In the 1950s, Knight was a minimally employed illustrator, who happened to become friends with D.D. Ryan, a well-connected neighbor in New York, who introduced him to Kay Thompson, the singer, actress, and would-be author of the Eloise series. “Kay and I went to work within a few weeks, and the book came out in 1955,” recalled Knight. The full story of how Knight became wrapped up in Thompson’s world—traveling with her to Paris, embedding himself in her circle of friends—and then his subsequent alienation—being abandoned by her, and forbidden from drawing Eloise—plays out in the documentary. But, as Dunham makes clear, Knight’s career didn’t end with the final Eloise book. Today, Knight has many ongoing projects, such as the many personal films he makes at his home in Long Island, and the new book series, Olive and Oliver, which he is writing with his twin nieces. Also, at 88, he stays on top of pop culture. “Oh, I love Girls,” he said. “I love everything about it—the writing and acting. They’re fantastic, smart kids. When I met Mamet’s daughter [Zosia, who plays Shoshanna], a week later I got a letter from her—not an email, a handwritten letter. I didn’t know kids still did that.” Some Girls stars do, apparently—and maybe they’ll even pose for next year’s holiday card.

It’s Me, Hilary: The Man Who Drew Eloise premieres March 23rd, 2015, on HBO.