Canto was originally inspired by Edward M. Catich’s seminal thesis on the origins of the Roman inscriptional style, such as that found on Trajan’s column. But Canto’s more personal origin story stems from a vivid dream Lipton had. In the dream, he was running his fingers along a V-cut inscription of some ancient Roman artifact. Glancing to his right, he noticed an old man with a worn, flat brush laying out letters on the stone, with fluid and deft precision, rendering the most elegant Roman capitals. When Lipton tried to ask the man a question, the dream vanished before he could speak.

By an odd coincidence, Canto was used in an inscriptional project long before it was completed or even named. Some friends of Lipton had lost their seven-year-old son in a grievous playground accident; they wanted to have a memorial stone bench at his gravesite. They asked Lipton to design the lettering for the message that would wrap around the flat edge of the granite seat. The early drawings for Canto seemed appropriate for an inscription; this heartfelt project pushed Lipton to further develop and complete the family.

He drew a full set of lowercase letters—a crucial feature missing in other digitizations of the Trajan capitals—and fleshed out the character set. He also created two variants suggesting different tools: the refined Canto Pen and the expressive Canto Brush. Canto’s new expansion doubles the two weights to four for each version, extends their character sets and adds many ornaments, and outfits them with a companion italic inspired by the inscriptional work of Fud and Nick Benson of the John Stevens Shop in Newport, Rhode Island.

Every type family contains a lesson. Bennet taught Lipton that it’s okay to abandon an initial idea if it leads to something more interesting. The typeface grew from his admiration for Moth Design’s hand-drawn logotype for The North Bennet Street School in Boston. As Lipton quickly sketched letterforms early in the project, one of the sloppier vertical stems slightly bulged in the middle. This happy accident caught his eye, slowed him down, and eventually became a chosen stylistic attribute that fit in nicely with other qualities Lipton was pursuing for the design—something akin to Dwiggins’ desire to create “warm-blooded” letters.

The contrasting interplay between inside and outside shapes lends the Display and Banner optical sizes an expressive, sparkling quality, while adding a vibrant rhythm to the text. Graded text styles are a bonus to the comprehensive family.

With Meno, Lipton wanted to create a versatile and practical serif-based family on an influential historical style. The types of French punchcutter Robert Granjon, who was active in Paris in the mid-sixteenth century, served as its model. Lipton’s motivation was similar to Matthew Carter’s for designing Galliard: “not to create a literal copy of any one of Granjon’s faces—more a reinterpretation of his style.”

What sets Meno apart from other contemporary versions is its sophisticated calligraphic air. Meno’s expressive italics can easily be used as standalone display fonts; with the swash variants, they invite comparison to graceful calligraphy. The expanded family now counts three optical sizes: Text, Display, and Banner; the Display and Banner styles also come in Condensed and Extra Condensed widths.

Lipton has always been drawn to a sense of the dramatic in the work of both historical and contemporary master calligraphers. This drama can take many different forms: contrasting pen or brush weights, letter styles, or a dynamic layout and flourishing, for example. The late Raphael “Ray” Boguslav’s natural flair and his particular talent for translating historical scripts into contemporary letterforms informed Lipton’s approach to Sloop.

In the 1980s, artist John Mecray commissioned Boguslav to letter the nameplates and titles for a series of paintings of classic racing yachts. These swooping letters prompted Lipton to develop an original, classically elegant script that was roughed out with a narrow broad-edge pen and then refined in the digitization process. The steep angle and vigorous ascenders and descenders in three different lengths create an impression of weightlessness and speed. Capitals with two levels of embellishment allow the user to get the type just right.