Tobias Frere Jones, founder and design director of the eponymous foundry, designed the popular Interstate and Garage Gothic typefaces. “The lowercase ‘a,’ is a perpetual oddball,” he says. “Most letters of the alphabet have deep alliances with each other, sharing bowls, serifs and terminals.” On the other hand, he notes, “the ‘a’ stands apart from those tight cliques with a collection of one-off shapes. It also appears over and over, potentially arguing with its neighbors in a word. For the type designer, the lack of precedent and the frequent use make it a test of confidence and fluency in the design at hand. Standing up, sweeping over, springing out, looping back, always with its feet on the ground — a designer has to be deep into the substance and spirit of a typeface to be able to draw this."

Chank Diesel (a.k.a Charles Andermack) is the creator of Minneapolis-based Chank Fonts. He says one of his favorite creations is the capital “M” from Adrianna Demibold. “It seems like such a simple letter, but I love how it differentiates this simple sans font from all the other sans serif fonts out there. Every other 'M' seems more uptight by comparison, almost always with straight vertical shoulders, while the sides of my “M” are slanted just a bit to reflect a more relaxed stance. The middle bit goes all the way to the baseline and gives it extra support. And I also like that it’s really wide, like an M should be; some 'M's suck in their guts to try to be as narrow as all the other letters, but this 'M' is confident in its extra width, proud to be wider than other letters."

Chester Jenkins, co-founder of the type design collective Village Type, created the Brooklyn Sport and Sport Stencil typefaces for the massive Barclay Center arena. In 2007, Michael Bierut of Pentagram hired Jenkins to design a series of typefaces for use throughout the future Atlantic Yards development. “I based my sketches on memories of the renderings of Frank Gehry's work,” Jenkins says. The first finalized part of the project was the arena's "Sport" font in regular and stencil versions. “I particularly enjoyed the challenge of making the heaviest weight of the type into a stencil, where space was tight and there could be no cheating; the stencil wasn't for style but for functionality. Of all of the letters in the heaviest weight of the Stencil, my favorite is the 'k'. For the most part, I adhered to the non-stencil design of the letterform, but subtly tweaked the angled strokes in order to create a mirrored triangle. It's a little detail, but it makes me happy.”

James Montalbano, director of Terminal Design, has designed dozens of typefaces, including ClearviewHwy, Choice Sans and Kinney. When it comes to drawing, Montalbano’s favorite Latin letter is the double bowl lowercase “g”. “I have an affinity for the shape and never felt it was difficult to draw,” he says. "I love the way the ear has to balance the lower bowl and how it has to be restrained enough to not draw too much attention to itself.”

Veteran illustrator and designer Seymour Chwast, who co-founded Push Pin Studios, has designed classic display faces including Chwast Artone (1965), Chwast Buffalo (1978), and Beastial Bold (1980). “I love ‘A’s,” Chwast says. The letter is the cornerstone for the identity Chwast created for Artone Ink, which has become an icon of 1960s graphic design. “I’ve been told that it reminds people of a drop of ink. Its style, with all the letters having big bottoms, is Art Nouveau, and was very popular when the alphabet first appeared."

Jonathan Hoefler, founder and director of type foundry Hoefler & Co., has designed typefaces for publications and institutions ranging from The New York Times to The Guggenheim. “When I’m drawing a new typeface, or developing one with the designers at H&Co,” he explains, “a favorite moment is always the ampersand. It’s always an opportunity for adventure; even the most conservative typefaces can give sanctuary to a whimsical ampersand or two. Or three. I’ve been known to draw them to excess.”

Daniel Pelavin---whose work includes illustration, typographic, lettering, and icon design---has designed over a dozen display faces, including Anna, Tiki, and Hi Fi. “I regard letters not for style but for the way they empower humanity,” he says. “From runes traced in sand, to pixels viewed with careful deliberation at the top of a subway stairs, every incarnation has helped us forge ahead. I have no favorites but, most appreciate decorative and novelty typography that enhances and reinforces content. Letterforms from the late 1800s to the mid-1950s provide my greatest inspiration, however, like every designer from the Vienna Secession onward, I like to pretend that I am creating forms not previously in existence.”

Mark Simonson, founder of the eponymous studio, has designed dozens of fonts, including Coquette, the Felt Tip series, and Proxima Nova. His favorite letters are "S" and the serifed “E.” “The serifed E is the letter I find myself drawing over and over in idle moments,” he says. “The basic form is just horizontal and vertical strokes, and then it’s got all these different kinds of serif shapes to play with. Letters are like faces to me, with different expressions. The capital “E” faces to the right and has a severe, dignified expression. It’s also the most common letter in English and many other languages, so the way it looks has a big effect on the way a typeface looks.” “The 'S' is the most beautiful letter and one of the most difficult to draw well. It’s the opposite of the 'E,' formally: all curves, no straights (usually). It’s deceptively simple. You would think you could draw it with a compass—two linked circles—but you can’t. It won’t look right. Even the most geometric-looking S will not be drawn that way. Like the “E”, it faces to the right. Its expression is distant, and graceful, and in some styles appears to have long, flowing hair.” Pictured above are an "E" and "S", from Simonson's Bookmania and Kinescope typefaces, respectively.

Sophie Elinor Brown is a custom lettering artist and type designer from Australia. "Like every other warm-blooded designer," she says, "I have an affinity for ampersands. Much like the Q, it’s their versatility that draws me in. What started as a humble Latin ligature is now expressed through a plethora of wildly different structures. No other character is like that, which makes the ampersand delightfully playful. As a recovering letterform addict with a bad sense of humor, I went through a very consuming phase of illustrating ampersand-related puns: “yes-we-can-persand”, “rubber-band-persand”, “cyan-persand” and “amper-santorini”, to name a few…”

Peter Bil’ak founded the Dutch type foundry Typotheque. Of his many faces, Fedra is his most well known. Bil’ak says his favorite letter is usually from a typeface he is currently developing. This one, ‘AE,’ is from a digitial typeface called Uni Grotesk that Typotheque will publish in full later this year. “It’s an adaptation of a Czech grotesk that dates back to the 1930s, and is one of my favorite letters at the moment.”

Sara Soskolne, a longtime designer at Hoefler & Co., has worked on the designs of Sentinel, Chronicle, and Tungsten."Beyond the basic alphabet, another treat lies in store; a character that I unfailingly love to draw is the eszett, or the German sharp s,” she says. “It takes up more real estate than the rest of the Latin lowercase, so it can feel quite roomy---but a lot has to happen inside that space. It also has a very satisfying asymmetry: rising up from the baseline in a straight line, resembling the left half of the f, it then sweeps over to the right much more grandly than the f ever has room to do. Then, its more unique right side might take any number of forms — bulbous, angular, continuous, or some combination thereof. My favorite by far is the continuous form, a sinuous cascade containing a series of turns and tumbles which require considerable discipline to bring into a balance of fluid tension with each other, and make it the closest thing to a rollercoaster inside the Latin alphabet — both to look at and to draw.” Above are ten examples of the eszett shapes found in the H&Co library.

Type designer Dan Rhatigan (A.K.A. Ultrasparky), the former creative director and archivist for Monotype, does not wear his favorite letters on his sleeve, but they are indelibly tattooed on his arms. Take the 'z' on his left tricep. It comes from François Boltana’s display script Stilla, first released by Letraset in 1972. Rhatigan calls it "the most captivating 'z'" he's ever encountered. "Stilla is an alphabet of bold flourishes and delicate details, and can be incredibly tricky to use well for more than a word or two at a time. Of all its shapes, the 'z' (and similarly, the 'Z') is the standout for me. It has so much energy, so much contrast, such perfect balance of fine and full-figured strokes. Some of the other characters in Stilla can feel like a compromise, but the 'z' is a masterpiece."

Brazil-born typographer and graphic designer Yomar Augusto designed the typeface Global Heavy. His favorite letter is the uppercase “R”. “It has an incredible force that combines vertical, horizontal, diagonals and round shapes, carrying almost the entire DNA of an uppercase family," he says. Pictured above is a Layered "R' from Augusto's "All About My Maps" project.

Michael Doret, a custom letterer and type designer and founder of Alphabet Soup Type Founders, designed Power Station, Dynascript and Metroscript, among other typefaces. “I have always thought that the ampersand was by far the most interesting character,” Doret explains. "It's my favorite because its various twists and turns allow almost limitless design variation—it's kind of a blank slate upon which we are free to create, and for whom legibility problems have never seemed to be an issue.”

Xavier Dupre is a French-born type designer who has created original faces for FontFont and Emigre. Based in South-East Asia, has also designed Khmer language typefaces in Cambodia. Dupre believes ITC Mendoza roman to be the most beautiful French typeface of the 20th century, his favorite letterform being the lowercase ‘a’. “It has a strong impact and is well balanced,” he says, “very masculine and aggressive on the outer part of the counter with a dark bulge on the left part, a foot straight and deep in the ground but without any angles, all is rounded, feminine, the closed counter is quite informal.” José Mendoza y Almeida designed this family in 1990. The 3 weights have been drawn by hand. “A masterpiece,” he says.