The Trippy ’60s, Courtesy of a Master

The graphic designer Milton Glaser, left, in his Manhattan office with Matthew Weiner, the creator of “Mad Men,” for which Mr. Glaser has designed ads that will start appearing next week.

IN the world of “Mad Men,” whose seventh season begins on April 13 on AMC, one of the central dramatic devices is the client meeting, the scene where the advertising gurus and the people who pay them gather in their glassed-office agora to wrestle over the nature of commerce, persuasion, art and desire.

On a recent morning in a townhouse office on East 32nd Street in Manhattan, reality was treading closely, and somewhat strangely, in fiction’s footsteps. The client sitting in the conference room, waiting for his real-life ad man, was the show’s creator, Matthew Weiner. And the ad man was not just another bright, creative type from the art department. It was Milton Glaser, who — probably more than any graphic designer of his generation — forged the sophisticated, exuberant advertising look of the late 1960s, the time “Mad Men” is now traversing, and whose work to publicize the show’s new season will begin appearing next week on buses and billboards around the country.

“I can’t believe this is the first time we’re meeting, after all your work,” said Mr. Weiner, shaking Mr. Glaser’s hand. “Hi. I guess I’m the client.”

“No higher calling,” said Mr. Glaser, smiling as he took off his coat and hat and welcomed his guest.

Credit...Milton Glaser

Over the years of producing and writing the show, Mr. Weiner has become something of a student of graphic design and commercial illustration. And he said he had long dreamed of Mr. Glaser’s having a hand in the show’s ads — not only because of his renown as the creator of the ubiquitous I ♥ NY logo and other images, but also because he embodied the ethos of the era, as the clean-lined, clean-conscience advertising of the 1950s and early 1960s fractured, along with the culture, into something more chaotic, self-doubting and interesting.

“I grew up with a poster by Milton in my house, which my parents bought at MoMA,” said Mr. Weiner, 48, describing a 1966 promotion for WOR-FM radio, now in the collection of the Museum of Modern Art, showing five Beatles-esque performers rendered in a wildly colorful style that evoked both Art Deco and hard-edge painting.

Indeed, Mr. Glaser, 84, with his imposing bald pate, goatee and wry professorial air, could easily be a character on the show, a seen-it-all Zen master from the creative department. “I could have walked in the door of that firm,” he said, of the fictional Sterling Cooper & Partners. “I knew those people.”

Mr. Glaser still runs his small firm out of the Beaux-Arts townhouse he bought in 1965, the building where, three years later, he also helped found New York magazine with Clay Felker. The transom glass above the front door still bears the words “Art is Work,” and Mr. Glaser continues to live by the axiom. In recent years, the firm has been responsible for widely seen work, like the logo for the Brooklyn Brewery, covers for The Nation magazine and the logo and posters for Tony Kushner’s “Angels in America.”

When Mr. Weiner and the “Mad Men” promotional team began thinking last year about their hopes for an ad aesthetic as the show approached its last two years, someone took one of Mr. Glaser’s best-known images, a 1966 Bob Dylan poster inspired by a Duchamp silhouette self-portrait, and cut out the psychedelic flowing hair with which Mr. Glaser had crowned Mr. Dylan. The hair was then pasted upside down, like a Technicolor eruption, and sent to Mr. Glaser as an inspiration.

“I was in love with the idea that we could, in a way, rope him into the narrative of the show,” Mr. Weiner said.

As often happens with “Mad Men” clients, Mr. Weiner ended up communicating with Mr. Glaser only through intermediaries, and he was meeting him for the first time that morning. Mr. Glaser said that situation suited him just fine.

“I don’t like to talk to anybody because I always want to have my way in everything,” he said.

To which Mr. Weiner responded: “And I want to talk to everybody because I want my way.” But he added, “Basically, once we decided that it was going to be Milton, I just deferred to him.” Mr. Weiner said he made it known in broadly general terms that he had in mind only something “a little furry” and “kind of Luddite, I guess” and “as strange as it might sound, something with flowers.”

Mr. Glaser said his concern was trying to make work that suggested a late-1960s feel without pillaging his own late-1960s feel. “I haven’t been working this way for 30 years or so,” he said. “My anxiety was that people would think, wait a minute, I’m still doing this sort of thing.”

The poster and ads he came up with read like a sly reappropriation of his past, a shaggy explosion of color, flowers and Art Nouveau curves on top of which is the by now familiar back-of-the-head silhouette of Don Draper with his arm extended over a chair and a cigarette in his hand. What first reads as abstraction resolves into a profile of a woman’s face, the spire of the Chrysler Building and a glass into which wine is being poured.

Credit...Milton Glaser

“There is a dreamlike quality to it, and believe it or not, it is related to the show, and not because it’s psychedelic,” said Mr. Weiner, dressed appropriately for the period, with a buttoned-up suit vest but also a bright pink patterned tie. “That’s not what it’s about. What it’s about is the material and the immaterial world, and that’s what I loved.”

Did the imagery hold any clues to the season, beyond Don Draper’s affection for women and drink? Mr. Weiner, known for being unforthcoming with plot details, said, “This is related to the late ’60s, which is all I will say about it.” He added, “It maintains the idea that this is somehow going on in Don Draper’s mind, which is what the story is always about — and what the back of his head is about, on some level.”

Mr. Glaser, who works at a battered, easel-like desk with no computer and a profusion of Tibetan and other Eastern art pinned up on the wall above it, drew the imagery for the ads by hand, something he doesn’t get to do nearly as much as he used to.

“It really turned out to be a lot more fun than I thought it would be,” he said. This was partly because it allowed him to think again about the deeply unsettled time he helped define, when New York was sliding toward near-insolvency, the country was mired in war, disillusionment was profound, and yet there was still a field called advertising whose job was to sell dreams and create desire. Occasionally, he said, it had — and still has — the power to transcend commerce and speak to the human condition.

“The search for that thread, the experience that we all feel rooted in, is what we do — that’s the best thing we can do,” Mr. Glaser said, adding with a shrug and a smile, “And if you can’t live with contradiction, get out of town, right?”

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