In 1962, Barbra Streisand channeled all the emotional turmoil and lyric despair of an abandoned lover into what must be the strangest four minutes of pop music ever written. “Crayons ready?” she croons, “Begin to color me.”

The opening lines of the song, “My Coloring Book,” refer to that year’s fevered interest in coloring books for adults, much like the trend that has taken off recently. “For those who fancy coloring books / As certain people do,” Streisand sings, before asking listeners to fill her sorrowful life with equally sorrowful hues. When the song came out, coloring books for adults permeated pop culture, as Mort Drucker’s JFK Coloring Book spent 14 weeks at the top of the New York Times bestseller list in 1962, and sales of adult coloring books reached $1 million. Today, coloring books are perhaps even more profitable: Johanna Basford’s Secret Garden and Enchanted Forest were the two best-selling books on Amazon in April, responsible for some of the year’s recovery in print sales. (Basford has sold nearly 10 million coloring books since Secret Garden was published in 2013.) But their powerful appeal—enthusiasts say they are a “great way to de-stress”—has very little in common with adult coloring books from the 1960s. Where today’s titles offer consumers a neat package of therapy, escape and nostalgia, 1960s coloring books were both genuinely novel and subversive.

The first adult coloring book, published in late 1961, mocked the conformism that dominated the post-war corporate workplace. Created by three admen in Chicago, the Executive Coloring Book show pictures of a businessman going through each stage in his day, as though teaching a child what daddy does at work. But the captions, which give instructions on how to color the image, are uniformly desolate. “This is my suit. Color it gray or I will lose my job,” reads a caption next to a picture of a man getting dressed for work. Another page shows men in bowler hats boarding their commuter train. “This is my train,” it reads. “It takes me to my office every day. You meet lots of interesting people on the train. Color them all gray.” The rare appearance of a non-gray color is even more disturbing: “This is my pill. It is round. It is pink. It makes me not care.”

From The Executive Coloring Book, 1961. Ad to the Bone

The coloring books that followed managed to cover, between them, a selection of the decade’s neuroses: national security, the red scare, technology, sex, mental illness. Two popular books took aim at President Kennedy: Drucker’s JFK Coloring Book and Joe B. Nation’s New Frontier Coloring Book. There were coloring books that made fun of communists and coloring books that made fun of people who were scared of communists. Khrushchev’s Top Secret Coloring Book: Your First Red Reader caricatured Soviet leaders and life under communist rule, but was still deemed “objectionable” and banned in the United States Military. Meanwhile, the John Birch Society Coloring Book, which ridiculed conspiracy theorists and extremists, stretched the coloring book concept to its limits with a blank page, captioned: “How many Communists can you find in this picture? I can find 11. It takes practice.” In August 1963, the Washington Post reported on a doctor who proposed using a 12-page coloring booklet “as a diagnostic tool…to classify patients by their types of disorders” from schizophrenia to brain damage. The Post called it the “Psychotic’s Coloring Book.”

From the John Birch Society Coloring Book, 1962. The New York Times archive

From the New Frontier Coloring Book, 1962 The New York Times archive

As the trend wore on, the books’ targets became more predictable. Publishers ridiculed occupations and lifestyles that already looked ridiculous without their help. The Bureaucrat’s Coloring Book, for instance, made fun of government commissions and regulations. The Hipster Coloring Book made weak jokes about the flatness of a supposedly daring lifestyle. The captions became more knowing and metaphorical. A picture of a smoking jacket-clad young man says: “He has a fun time… Color the gleam in his eyes brightly.” 1963’s Programmer’s Primer and Coloring Book made complicated jokes about bugs and core dumps with bizarre instructions to “Color me Mickey Mouse” and “Color him naïve.” They lacked the straightforward sadness of The Executive Coloring Book’s instruction—made sadder because so plausible—to “Color me gray.”