Frere-Jones grew up in Brooklyn, in a family of writers who revered books; his father wrote for advertising agencies, and his older brother, Sasha, would become a music critic. He used to follow his father to work on weekends, combing through offices vacated by people who had left the company “for free art supplies,” he recalls. “My first type-specimen book was rescued from a trash bin on one of these weekend visits.” The idea that there were such things as “typeface designers,” people whose job was to draw letters, struck Frere-Jones with great force: Designing alphabets, he’d later say, seemed like “designing water or designing air.”
He went to the Rhode Island School of Design and started drawing typefaces. Soon a professor introduced him to Matthew Carter, perhaps the preeminent living type designer, and by age 20, Frere-Jones had published his first commercial font, a funky design he’d sketched on a napkin (for a band his brother was in).
Frere-Jones is so prominent now—“one of the two or three best type designers in the world,” according to Erik Spiekermann, a German type master—that it’s easy to assume his success was inevitable. But he probably owes some part of it to auspicious timing. He happened to be entering the field at the dawn of a type revolution. It used to be that there were just 2,000 or 3,000 fonts in the world, pieces of actual metal, and only designers knew their names. The personal computer was changing all that. Now anyone could type a document in Palatino or Times New Roman or Helvetica. People suddenly had relationships with fonts. And because it was so much easier to create and market a purely digital font than a physical one, individual designers or small groups could sell fonts of their own. A new generation was about to make its name.
Type is a derivative form. A designer starts not with a blank canvas but with a set of rules for creating letters and the knowledge that thousands of others have interpreted the rules stretching all the way back to Gutenberg. Even by his early 20s, Frere-Jones knew enough about type history to avoid repetition and create shapes that seemed contemporary. He also had a monastic sort of patience. He could sit in his office and tweak the thousands of small details required to bring a high-end font family to completion: the endless “kerning pairs” that determine the spacing between letters; the multiple weights and widths of a font that allow designers to make words lighter or darker or narrower or wider as they please; and the cooperation of all the shapes with each other—the lowercase and the uppercase, the light and the bold, the roman and the italic—so that anyone using or reading the font will experience “a sense of balance and organization on multiple levels,” he says. “It’s like trying to conduct an orchestra with, I don’t know, 500 people in it.”
In Boston, working for a company called Font Bureau, Frere-Jones racked up a number of successes, including Whitney [ fig. 4 ], a sans-serif font that made magazine infographics look more modern, and Interstate, a display typeface inspired by American highway signage. He liked his job, but after several years, it started to bother him that he was designing fonts for other people instead of for his own company. But he knew a guy who didn’t have that problem, and because the type world is small, they started talking about it together.
In some ways, Jonathan Hoefler was a lot like Frere-Jones. They’d both grown up in New York, and they’d both fixated on type at a young age. But Hoefler had chosen a different, more entrepreneurial path forward. He’d gotten his start at 17, clocking hours at a service bureau in Manhattan, the kind of place where people would bring files on floppy disks to have them typeset by professionals; laser printers weren’t yet affordable. There he met Roger Black, a prolific magazine designer (Esquire, Rolling Stone, The New York Times Magazine), and the following year, 18-year-old Hoefler started hanging around Black’s studio. “Like a lot of smart kids, he was sometimes insufferable, but other times adorable,” Black remembers. After learning that Black was fond of an archaic font called Egiziano, young Hoefler created a version of Egiziano just for Black, as a gift. “It was beautifully done,” Black says. “Very ingratiating. And I actually used it.”
Unlike Frere-Jones, Hoefler never set out to become a type designer specifically. What excited him about type was what you could make with it, what you could say: “It wasn’t just the typeface, it was the complete communication.” But because electronic publishing was still new, most digital fonts then were of poor quality, so he had to make his own. Art directors kept asking him where he was getting these great fonts, so in 1989, he hung a shingle as the Hoefler Type Foundry and started drawing alphabets for money. He remembers Sports Illustrated calling him: “Let’s do a typeface that feels masculine but doesn’t undermine that this magazine is about journalism. It works for Michael Jordan, but also for the Ukrainian gymnast who breaks her ankle the week before the Olympics [ fig. 5 ].” He also drew a font for Apple he called Hoefler Text [ fig. 6 ], which became standard on every Mac.