Chilling with advertising guru George Lois for two hours is probably the most fun I’ve ever had with my clothes on.

Lois, the renowned ad executive, art director and designer, recently gave me a personal tour of his exhibit at The Museum of Modern Art titled, “George Lois: The Esquire Covers,” which runs through March 30, 2009. The museum has prints of 31 of the 92 covers Lois created for the magazine from 1962 through 1972.

I was a bit nervous at the prospect of interviewing a living legend. But Lois immediately put me at ease, providing lots of laughs (about working with Andy Warhol and dealing with the Nixonites, for example) and every now and again lightly poking me in the shoulder, as if to say, “Pay attention! This is important stuff.”

And it is. The exhibit is a veritable history of the 1960s. In a simple yet compelling fashion, the covers tackle the issues that gripped the country during that momentous decade: the onset of the civil-rights movement, feminism, hippiedom, the generation gap.

Nor do the covers shy away from all the violence that engulfed the 1960s: the assassinations, the Vietnam War, the rioting between police and protestors during the 1968 Democratic National Convention. To the contrary, the covers make one confront these issues that, for many Americans, continue to resonate.

Yet plenty of the covers display Lois’ unique brand of pranksterism, including Norman Mailer as King Kong holding Germaine Greer (as Ann Darrow) to portray the verbal fisticuffs the two writers had back in the day and the famed TV host Ed Sullivan wearing a Beatles mop-top wig. (The Beatles first made waves in the States appearing on Sullivan’s show in 1964.)

Whatever the decade, Lois has been able to capture the Zeitgeist. It goes back to when he was a wunderkind with the ad agency Doyle Dane Bernbach (DDB), the agency that gave birth to Big Idea Thinking. Lois’ first agency, Papert Koenig Lois, created memorable campaigns for Aunt Jemima, National Airlines and Xerox (a chimpanzee easily using a photocopier). Those campaigns led to the gig doing covers for Esquire, where he would revolutionize magazine design.

In addition to the iconic Esquire covers Lois created the concept and name for the low-calorie Stouffer’s product Lean Cuisine (1979) and created the “I want my MTV” campaign (1982). During a cab ride downtown I asked Lois about the MTV campaign and he responded, somewhat sheepishly, “Yeah, I destroyed the culture.” Nah. More like chronicling the culture — for the last 40-plus years. Not an easy thing to do.

Call him the Buddha of Madison Avenue. Aware, enlightened and oh so kind. And at 77, he’s still going strong, currently running the boutique ad agency Good Karma Creative, with his son Luke.

This piece marks the maiden voyage of From Print to Digital: On Location.

Enjoy.