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George Wayne has a theory about why his celebrity column has been a hit at Vanity Fair for more than two decades: sex.

“When you read my interviews, I want you to have a good laugh and I want you to learn something you didn’t know about these people before,” he said as he dipped his spoon into a bowl of butternut squash soup over lunch in Chelsea recently. “So, of course, I am always going to ask about sex. That’s my No. 1.”

Mr. Wayne, 54, was born in Jamaica and earned a degree in journalism from the University of Georgia before moving to New York. In 1984 he started his own magazine, R.O.M.E., a do-it-yourself collection of interviews he photocopied on paper and bound together with tape. He met Andy Warhol and, after the artist died, became an associate editor at Mr. Warhol’s Interview.

Later, Mr. Wayne caught the eye of the media scion S. I. Newhouse Jr. and was named one of the first contributing editors at Allure magazine. But it was at Vanity Fair that Mr. Wayne (who calls himself G. W.) found his niche as a celebrity chronicler. “I interviewed Fabio,” he said. “He was my very first interview at Vanity Fair.”

His interviews are sass with a dose of shock and often a bit raunchy. (He once asked the comedian Milton Berle if he still had orgasms.) Mr. Wayne described a 1993 encounter when he was invited to attend the opening of the first Western club in Moscow. “They flew over a motley crew of fabulous New Yorkers,” he recalled. “It was me, André Balazs, Martha Stewart and Gael Greene.”

Mr. Wayne met a man in Pushkin Square — a boxer in training, he said — who he invited to his hotel. The writer decided to stay a few extra days. “Martha Stewart’s jaw dropped,” Mr. Wayne said. “She said, ‘Why are you staying? Are you kidding me?’” She had a point. Violence erupted in Moscow after Boris Yeltsin, the president, sought to disband the Russian parliament and seize control. “I turned on CNN after having the best sex with this Russian boxer and there is a coup taking place in the country,” Mr. Wayne said.

We decided to turn the celebrity tables on Mr. Wayne and ask him some of the same questions he asked notable luminaries, among them Carrie Fisher, Ivanka Trump, Anna Wintour and his old boss at Vanity Fair, Graydon Carter. Many were lifted from “Anyone Who’s Anyone: The Astonishing Celebrity Interviews, 1987-2017,” a collection spanning Mr. Wayne’s 30-year career. We didn’t tell Mr. Wayne until the end of our interview that the questions were his. (His answers are edited for context and space.) And, yes, as you might imagine, we brought up his No. 1 topic.

Laura M. Holson: What’s one of the most outrageous rumors you’ve heard about yourself lately? (a question posed to Carrie Fisher)

George Wayne: Lately? That I’m drunk. No. I haven’t heard any. I never Google myself. I have no idea. I don’t listen to rumors. So I don’t know. You are asking the wrong person.

“When you read my interviews, I want you to have a good laugh,” Mr. Wayne said.CreditJackie Molloy for The New York Times

LH: Have you ever done drugs? (Farrah Fawcett)

GW: I’ve dabbled in some things, not everything. Growing up in a country like Jamaica, people think that you smoke marijuana, ganga, like a ganga head. The first time I did marijuana was in college. I think marijuana is the weed of wisdom. It heightens your creative abilities. That is basically what I do. I’ve never tried the hard stuff. I’ve tried Molly once. Ecstasy.

LH: Who is the phoniest person in Hollywood? (Joan Rivers)

GW: That’s a tough one. Can I think about that and get back to you?

LH: No. You have to tell me now.

GW: Angelina Jolie. That is just my personal opinion. She is a bit of a phony baloney.

LH: Have you ever interviewed her?

GW: No, I’ve never interviewed Angelina. After what she did to Brad, really? I’m not buying any of that stuff she said about Brad Pitt.

LH: If there is one vice, what would it be? (Ivanka Trump)

GW: I love champagne.

LH: That’s not a vice.

GW: It is a vice. I love champagne, but I love to drink champagne with orange juice, passion fruit and vodka. It’s called the G.W. Mimzy. You have to try one before you leave.

LH: How much time do you spend in front of the mirror each morning? (Fabio)

GW: Oh my God. Not very much at all. I take three showers a day. I do. I like to take them all the time. I use Mario Badescu. That, I live by. I don’t get the facials. I get their products. Serums, which I love. And the shaving cream.

LH: How big are your arms? (Fabio)

GW: My arms are O.K., they aren’t big. I work out. I go to the gym.

LH: How is your sex life? (Milton Berle)

GW: I’ve been, basically, celibate a long time. I would love to be in a relationship. For some reason I never have sex in New York City. I would love to be in a committed relationship. But I’m very picky.

LH: What girls do you think are next in line for the title of world supermodel? (Donatella Versace)

GW: Without question, Kaia Gerber. She is exquisite. I saw that full page Omega ad she just did, the campaign for a new watch. She is stunning. She is like her mother, Cindy Crawford, plus more. She is the future. No question.

LH: Is it true you write all of your books in longhand? (Jackie Collins)

GW: I do. (He pulls out a stack of white paper stapled together.) These are some notes. I save everything. It’s like regular white paper. I cut it. I make little books. So if you come to my apartment, which is the size of this table, you’ll find nothing but filing cabinets and magazines. Filing cabinets with my notes.

LH: Tell me a little about your childhood. Was it privileged? (Anna Wintour)

GW: Yeah. I was a lucky kid. My parents gave me the best of everything, to be honest. My father worked with a Canadian company, a conglomerate. My mother sold real estate. And she drove a Peugeot. And nobody in Jamaica drove a Peugeot. I went to boarding school. It was called Munro College, where a lot of Rhodes scholars went.

I was on the quiz team. We won twice. The quiz competition in Jamaica is a big deal. It is like being on “American Idol.” All the high schools compete against each other on live television. And it’s a must watch. It’s called the Jamaica “Schools Challenge Quiz.” Four members from each school compete against each other. After we won, I was a super-stud on campus. I was a campus star. They loved me.

LH: What do you think about Donald Trump? (Ian Schrager)

GW: You know, Hillary Clinton wrote the book, “What Happened?” Well, what happened to “The Donald”? In the golden age when Donald and Ivana were together, he was amazing. Donald was a lot of fun. And I don’t know. It’s the strangest thing, what has happened. It’s like watching an ogre metastasize. I’m just thinking a lot of us knew the man who was so fun and so charming, he always had his quirks. Who knew that he would become this Islamaphobic, homophobic racist? I just can’t imagine where this all came from. Is it because of Steve Bannon, who has completely got his mind? It is disappointing to see that.

LH: Do you pack heat? (Geraldo Rivera)

GW: No. But maybe I should get some mace.

LH: Do you watch television? (Milton Berle)

GW: I love television. Basically I watch the BBC, to be honest.

LH: Are you watching “The Crown”?

GW: You know what? I don’t have Netflix! A friend of mine just sent me the last season of “The Crown” on my computer, which I am going to watch. To watch Netflix, you have to get a special TV, no?

LH: When are you inspired to write your material? (Sandra Bernhard)

GW: The funny thing is I like to write at night. I’m a night owl. I like to write when it’s 11 p.m. to about 2 o’clock in the morning. I need my eight hours of sleep. You ask me what my vice is? It’s sleeping. I like to get my beauty rest. I smoke a spliff and then I write.

LH: And what will be the title of your memoirs? (Graydon Carter)

GW: “Simply George-ous!” May I say, simply gee-ooorge-us!

LH: Do you like Edith Piaf or Charo? (Graydon Carter)

GW: Edith Piaf! Actually, I like the Pet Shop Boys.

LH: What does that have to do with Edith Piaf?

GW: Nothing. But I like their music. Edith Piaf is too maudlin for me. I feel like I’m at a dirge. But I don’t like Charo either.

LH: Did you think these were good questions?

GW: Yeah. For the most part.

LH: They were your questions.

GW: What? Mine? Are you kidding? I asked those questions over 30 years? You’re good. Oh my God. Do you pack heat? Oh, I love it. Brilliant. I can’t believe it. When did that come to you? That’s funny. But, I’ll tell you one thing. I have a weak bladder. I have to go pee. I’ll come right back.