This is a continuation of the blog series The Out There Side. This installment honors the late, great Milton Glaser.

Milton Glaser was one of the most famous designers of the last century, so it’s safe to say he’s the most famous designer I ever interacted with. I knew him from my days as editor of Graphis magazine, where he was a regular fixture, a wise elder, and a generous friend of the mag. He was also, of course, a monumental icon. As one family friend put it, I ♥ Milton Glaser.

Since his passing on June 26 at age 91, the tributes to Milton have ranged near, far and wide. When I mentioned to my wife that I felt inspired to blog about him, she said, “Yeah, you and everybody and their dog.” So I guess I’ll just join in howling with the choir. To wit:

In the New York Times, Jeramy Ellis shared a fascinating conversation with Glaser about one of his final creations, a graphic treatment of the term Together in response to COVID-19. A former editing partner, Martin C. Pedersen, ran a recollection of great quotes from the great man on the design and architecture website Common Edge. And B. Martin Pedersen, publisher and creative director of Graphis, shared a touching tribute to his old friend.

[Those two Martin Pedersens are not related, but they received each other’s mail for years. After they met and had drinks, the publisher hired the editor, and soon I was dealing with two Martins… We all sort of worked it out.]

At Graphis, we would always trot out an interview story featuring Glaser when we needed something interesting, because we knew he meant good copy, good art, good pull quotes and cover lines. As Martin C. Pedersen (the editor) told me recently, “You must have worked ten stories on Milton.” I replied, “You probably worked ten as well.” Milton stories ranged from a Q&A with Pete Hamill to a conversation with Tom Wolfe in celebration of Glaser’s book Art is Work. Most recently, Glaser was the cover subject for issue 364 of the Graphis Journal, a revival of Graphis magazine that I had helped to start up, along with my fellow freelance editor Lindsay Comstock.

The last time I saw Milton he was onstage at Cooper Union, in conversation with design writer Steven Heller about a new expanded edition of Glaser’s book The Design of Dissent. Among the other protest images discussed was the above picture (no retouching, the caption said) of the Nixon Eggplant, which Glaser published in New York Magazine. “Ridicule is a great tool because it allows you to deal with an opposition vantage point without reverting to anger,” Glaser explained. “You couldn’t help laughing at this image; you couldn’t help but think that Nixon was diminished by this image. And you have to wonder about those images that function in that way.”

My very first encounter with Milton Glaser’s work was a cliché: the poster of Bob Dylan with the kaleidoscopic hair. When I first noticed that, my little third-grade mind imagined a couple of things: Whoever drew that picture is really out there, and Bob Dylan must be something wild, too.

[After decades of following him I can attest that Dylan is something wild — though I never had an occasion to interview him, thank goodness! Legend has it that Bob is not the easiest of interviews. Meanwhile, a lot of my friends know the story of my infamous phone talk with another irascible songwriter: Lou Reed. Now that was something wild.]

But I digress: Milton Glaser, as a famous person, was the opposite of irascible. On the phone he was kind and funny and came off like a regular dude, albeit one with a sharp wit and a reservoir of sagacity. My favorite anecdote involves a little piece of gratis artwork. I was talking to Milton about something unrelated when I mentioned that we needed an illustration for a column, entitled “Finding the Common Ground.” I was thinking something about the blind men with the elephant parable. He said, “I’ll give it some thought.”

A day or two later, a tube arrived at the Graphis office by messenger with a poster-sized (36x24-in) crayon drawing of an elephant with blind men. Unsigned, but obviously Milton. We ended up running the illustration at 3x2-in along with the column, but I kept the poster. In those days I plastered my cubicle with memorabilia, and for years this picture was front and center.

Sadly, I left it behind when I left the gig and I’ve lost track of the drawing. Should’ve framed it. Milton didn’t charge us a dime for it, but I’m sure it would be worth plenty now.

Jack Crager is a writer and editor based in New York City (