When the first letter came, Tom Fitzharris was in no doubt as to who sent it. Drawn on the outside of the envelope was a clapboard house with an open window. Standing in the window was a little white dog, posed with great purpose. The dog had odd black stripes and a large T penciled on its side, as if it were wearing a college letter sweater. The simplicity, the wit, the elegant design—the sender was Fitzharris’s new friend, the American writer, artist, and Tony-winning theater designer Edward Gorey, known as “Ted” to those close to him.

Fitzharris met Gorey in 1974, outside the Town Hall in Midtown Manhattan. Gorey was wearing a large fur coat tucked under his distinctive gray beard, and the young photo researcher went up to him to ask about the French humorist Alphonse Allais, whose Story for Sara Gorey had illustrated. Did he have an English copy of the original? Gorey didn’t, but he did have the French edition and told Fitzharris to call him.

Phone calls led to a two-hour lunch, which led to escapades at the theater and Gorey’s favorite haunt, New York City Ballet. When Gorey left the city to summer on Cape Cod, he began sending letters. Over the next year and a half, he sent 50, all featuring little dogs, each etched with a T, for “Ted” and “Tom.”

Inside the illustrated envelopes Gorey placed quotes from his heroes—everyone from Paul Gauguin to John Cage. One, by Anne Thackeray Ritchie, reads, “But, after all, the whole secret of life is made up of the things one makes, and those one steals, and those one pays for.” Sometimes he included stranger items: a pew ticket from an 1800s church; a small piece of a crumbling Toulouse-Lautrec poster, with the artist’s signature barely visible. In 2000, Gorey died suddenly of a heart attack. He was 75.

A delightful new book, From Ted to Tom, collects the marvelous illustrations that Gorey sent to Fitzharris. Each image reveals secrets of Ted and Tom’s friendship—snippets of their conversations and shared memories. Toward the back of the book, there is a section of notes decoding some of the references behind the inside jokes and quotes. What a wonderful glimpse into the mind of one of America’s greatest illustrators.

“Ted was incredibly playful and loved to laugh, often at himself,” Fitzharris writes in the introduction. “When I think back on that time with Ted, that’s how I remember him: laughing.” —Elena Clavarino

Elena Clavarino is a Senior Editor at Air Mail