How does one interview their boss and friend of 47 years? Very carefully, unless your boss is Graydon Carter, whose gift for irreverence and self-deprecation is almost as legendary as his hair. His new memoir, When the Going Was Good (written with guidance from the wonderful James Fox), chronicles his life so far, which includes stints as co-creator of Spy magazine and, for a quarter of a century, as editor of Vanity Fair. He is quite the stickler for detail, always at the ready with a Blackwing editor’s pencil, but let the record show he changed none of these questions!

JIM KELLY: You grew up in Canada, and your account of your early years is by turns hilarious (realizing that one reason you quit playing hockey at 13 was that “whatever I was going to be doing in life, a complete set of teeth would be part of what I needed to get ahead”) and a bit scary (climbing telephone poles working as a lineman for the Canadian National Railway in Saskatchewan one summer). How do you think your Canadian upbringing shaped you?

GRAYDON CARTER: Playing hockey on an open rink in minus-30-degree weather certainly toughens you up for the road ahead. So there’s that. Working as a lineman for the railroad before college was also a challenging experience, but one I wouldn’t trade for anything.

Opponents would be wise not to underestimate the inner strength of Canadians. Generations of them have survived and thrived through brutal winters. They may seem soft and considerate on the outside, but there’s an inner steel under that smiling, affable exterior. Forget that nonsense about the 51st state. I think the U.S. becoming Canada’s 11th province has a nice ring to it. I believe that Americans would come to love tartan, curling, and butter tarts.

Growing up in Canada, about half of our outside culture came from the U.S., and the other half came from Britain. This gave young Canadians my age a good appreciation of the ways of both countries—their sense of humor, their character, and their customs. Canada is a sane, law-abiding country. Those qualities might be something to chafe at when you’re an idle, faux-rebellious teen. As you get older, they’re things you relish in a nation—never more so than right now.

As far as editing goes, I do believe that outsiders see the idiosyncrasies of a society with greater relish and clarity than those who have grown up within it. So many of the editors who made their marks in New York came from places that could never be described as cosmopolitan. The New Yorker’s Harold Ross came from Colorado. New York’s Clay Felker came from Missouri. And Henry Luce, who co-created Time, was born in China. I certainly wouldn’t put myself in their category, but I do feel being an outsider was a great advantage. Plus, if you’re Canadian, you can probably skate better than your competitors.

J.K.: Your mother gave you two books when you were 14: Act One, the acclaimed theater memoir by playwright Moss Hart, and Youngblood Hawke, Herman Wouk’s novel about a young writer trying to make it in New York. And so your yearning to be in New York began, ideally, in the world of magazines and the theater. “The city, that shimmering vessel of opportunity and reward, was where I wanted to be.” How romantic! How 1940s! Er, when you finally moved to New York in the late 1970s, how soon did you realize that, instead of shimmering, that vessel was actually teetering?

G.C.: I still have a tendency to see New York in black and white. Not all the time, but often. Like coming down the West Side Highway at dusk as the city comes into view. Or going up the East River Drive past 20th Street in the evening. In both cases, you see New York in all its illuminated glory and promise.

New York might have been a boiling cauldron of arson, murder, and drugs when I got here in the 70s. But it was a boiling cauldron of arson, murder, and drugs in New York! This is a city that always seems like it’s teetering on the verge of something. That’s part of the electricity of the place, I suppose.

And New York, more than perhaps any city in the world, is where young people go to become the person they want to be. That could be to live openly gay, or to become a theater rat, or, in my case, just to become the adult I wanted to be. I was done with my youth. I wanted an adult life of cocktails, cigarettes, and restaurants. And to be around people who were funnier and smarter than I was.

J.K.: You had a lot of fun as a young writer at Time, especially since you got to write the People page, a feature so successful that Time Inc. created a magazine from it. Yet you eventually left and started, with Kurt Andersen and Tom Phillips, Spy magazine, which for a glorious few years lampooned the rich and famous. What do you miss about the Spy days?

G.C.: Well, Time for me was the perfect New York finishing school. I was a hick from the provinces—the Canadian provinces, no less. You and I had a ball at the magazine, along with all our soon-to-be illustrious chums, Walter Isaacson, Kurt Andersen, Maureen Dowd, Michiko Kakutani, Evan Thomas, Pico Iyer, Frank Rich, and Alessandra Stanley. I had no idea people my age could be so smart and so composed. Also, we had cheap apartments and expense accounts. Who could ask for more?

As for Spy, I think you miss any time in your life when you had a full head of hair and a 32-inch waist—O.K., 34-inch. I miss the sheer joy of conspiring on stories for the magazine. But mostly I miss my fellow conspirators, many of whom contribute to AIR MAIL, which pleases me to no end.

J.K.: Sorry, but I need to ask about Donald Trump! You profiled him for GQ in 1984 and spent three weeks with him. In the piece, you noted that his hands were a bit too small for his body, which of course led to Spy’s famous description of him as the “short-fingered vulgarian.” In a TV interview back then, you also predicted that Trump would either end up storing his own urine in jars, like Howard Hughes, or being the most powerful person in the world. It’s on tape! What happened in those three weeks with him that made you so prescient?

G.C.: It was Trump’s first national exposure, and so he let me hang around with him for three weeks. I had no particular desire to write about him. But I was short of funds in those days, and I did it for the money. I portrayed him as a mauve-suited outer-borough sharpie in a stretch limousine—with vanity plates. He didn’t like that. I also pointed out that his hands were too small for his body. He really didn’t like that.

This observation, later magnified in the pages of Spy, set off our decades-long war of taunts and tweets—the taunts were mine, the tweets were his. On Twitter he called me “sloppy” and “dopey,” and he criticized my editing of Vanity Fair, the relative hotness of the Oscar party, and the food at my New York restaurant, the Waverly Inn. He even wrote that my wife thought I was a “major loser.” I checked with her that day, and she said she promised me that she never used the word “major.”

I did think that either full-on megalomania or madness was going to be in Trump’s future. Saying that he would either be the most powerful person in the world or that he would be storing his urine in Mason jars was a bit flippant, something I thought would be a good TV sound bite. For one thing, why should one preclude the other? Perhaps I was right on both counts. Has anyone ever checked his bathroom?

J.K.: You edited Vanity Fair for 25 years, quite a run in any business, let alone the magazine business. What was the most fun part of the job? The least fun part? And did you ever worry about getting fired?

G.C.: During my first two years at the magazine, I worried every day about being fired. Which was slightly terrifying in that I then had four kids to feed. During the remaining 23 years, I had daily panics about stories, staff, and competition—which was fierce in those days. During that golden age of magazines, the other editors were all at the top of their games, and it kept everyone on their toes.

As for the Oscar party, I loved the planning process, which went on for months. This, I have to say, was an enjoyable highlight of the job. Right behind that was leaving the Oscar parties, knowing that we hadn’t completely screwed things up. My wife and I would head back to our bungalow at the Beverly Hills Hotel and have a nightcap and talk through the evening with the kids.

Aside from the car and driver, what I miss most was the daily rhythm with colleagues I adored and trusted. Most top members of the Vanity Fair masthead were with me for my entire 25-year run. We’re still awfully close.

J.K.: No other magazine has created an annual event like the Vanity Fair Oscar party. What was the secret ingredient that made it so successful, did it get easier to stage year after year, and who was your favorite guest? Oh, and your least favorite.

G.C.: We did make it a bit difficult to get in. But once you were in, we treated everyone the same. There were no cordoned-off V.I.P. areas, as there were at most sizable events in those days. Everyone just milled around on an equal footing. I also made sure that we served good food and wine. For years, Thomas Keller handled all of that. We would have a morning-after recap each year to go over what we had gotten right and, more importantly, what we had gotten wrong. The party just got better year after year. And bigger. After the second year, the hard part wasn’t trying to get people in. It was who to keep out.

One year I invited all the men who had played James Bond. I thought the other guests would get a kick out of seeing them all there and that we might get a great group shot. The thing was, Sean Connery, Roger Moore, Pierce Brosnan, and Timothy Dalton were either working or on holiday. The only one who turned up was George Lazenby, an Australian actor who had done just one Bond film, On Her Majesty’s Secret Service, while Connery took a break. I spotted him at the bar. He was standing by himself, nursing a cocktail, and staring off into the middle distance. I thought it might be nice to go over and introduce myself. “Hello, Mr. Lazenby,” I said, “I’m Graydon Carter, your host.” He continued to stare straight ahead and then turned to me and said, “Fuck off!”

J.K.: There is the same air of exclusivity around the Waverly Inn in the West Village, and since I know no other magazine editor who also runs a restaurant, is there any overlap in the skills needed to create a desirable experience for readers as well as diners?

G.C.: Restaurateurs have very similar skills to editors. In the restaurant business, you forage for the best ingredients you can get at the best price, and you bring them back and use them to assemble dishes that you think will please your diners. In the magazine business, you forage the world for the best stories, assign the best writers and photographers you can lay your hands on, and then assemble all the elements into something that you pray readers will enjoy.

J.K.: You conclude your book with an informal set of rules for living, or, as one friend joked, the “Magna Carter: How to Be More Like Me.” The one that struck me the most (aside from the 25 uses for a handkerchief) is your advice not to have a “Wall of Fame,” a bunch of photos with famous people in your office and home. You have taken your own advice, in that there are no photos in your book! Only wonderful ink drawings by Eric Hanson. How much did you work with him, and since you are an artist yourself, were you tempted to do the drawings?

G.C.: I chose not to have photographs in the book because I thought that in a memoir or an autobiography, they can feel vainglorious and self-serving. They’re only useful if other, more interesting people are also in the photo. A corollary to my avoidance of a Wall of Fame in an office or home is this: Don’t include a photo of yourself with someone more famous unless you’re pretty certain that that person will have the same photo in their memoir.

As for illustrations in the book, there’s a big difference in being able to draw and being an artist. I love Eric Hanson’s work. He’s a proper artist. His drawings have a classic 50s air about them, and I just admire his line and his way of thinking. I saw a picture of his studio on a Web site, and it looked much like my own in Connecticut. We are very much of one mind.

Jim Kelly is the Books Editor at Air Mail