Photographer Jessica Craig-Martin dropped by Glenn O'Brien's Manhattan loft to shoot the polymath amid his staggering library and Warhol- and Basquiat-lined walls. O’Brien’s irreverent new book, How to Be a Man, details how to land an insult, organize a social diary, buy art, dress and drink. And O'Brien is quite the authority: currently GQ's Style Guy and a columnist for Vanity Fair Italia, his career arc includes editorial director of Interview (Andy Warhol gave him his first job), NY bureau chief of Rolling Stone, creative director for Chris Blackwell’s Island Records, host of cult cable access show TV Party, filmmaker (Downtown '81) and stand-up comedian, not to mention steelworker and singer. O'Brien wrote the intro to Craig-Martin's book Human Nature and invited her to appear in Wit, an online exhibition he is curating for Paddle8 in June. We spoke to the man who has been there, done that, and then some.
 
Who influenced your sense of style growing up?
My grandmother. Flora McGinty Sheldon. She caught me going out on a date once wearing a pink shirt and she said, "If I were that girl’s mother I wouldn’t let her go out with you." She felt you had to have a sense of occasion, a thing that men lack today.
 
Did you have heroes in movies to guide you early on?
Watching Cary Grant, William Powell, Fredric March and Gary Cooper was an education in good style. I saw the greatest Powell movie the other night: Jewel Robbery. He looks amazing. He’s an international jewel thief who falls in love with one of his victims and she falls in love with him and escapes her fat old husband. They go to Monte Carlo and abscond with a bit of money.
 
What was your early impression of New York?
I made my parents drive me to the Stork Club when I was 11 or 12. I knew that they wouldn’t fit in, so I said, “Wait here.” I presented myself to the maitre d’ and he was charmed and introduced me to all these people. That was always my goal—hang out at El Morocco or whatever. Because New York seemed really glamorous, and it was glamorous then. I remember going into Teddy’s and seeing Carl Sandburg the poet talking intimately with Liz Taylor and I thought, Wow, being a poet isn’t so bad.   

In the book you say that being a man means being everything a man can be. Can you expand on that?
When you read about the [classical] Greeks, a man could basically know everything. Now everything is so specialized I think it squashes people’s sense of ambition. I like that in France you can be a philosopher and go to nightclubs and date movie stars.
 
What is the best review you've ever received?
I gave my book [Soap Box] to Gore Vidal and talked to him about a month later, and he said, “Oh, I’m reading your book.” I said, “How am I doing?” He said, “I’m chuckling.” So, that was a thrill.
 
Any regrets?
If I knew I was going to live this long, I would have taken better care of my teeth. I sorta wish I hadn’t gotten married the second time. I wish I’d have gone from the first to the third.
 
What’s next?
I’ve been trying to decide whether to start a publication or not. And I wrote a script about Andy Warhol. I thought it would be good to have one that is about him, instead of one where he’s freaking out Jim Morrison or getting shot by Valerie Solanas.