A Portrait of an Addict as a Young Man

"I wanted to write exactly what I did and what I saw and who I did it with and how it felt. But I did not include every instance of my smoking crack. It would take an encyclopedia to tell that story," says Bill Clegg on a recent, resplendent June evening.

As a literary agent in 2005, Bill represented some of the country's luminary writers, like Nick Flynn (Another Bullshit Night in Suck City) Nicole Krauss (The History of Love), Susan Choi (American Woman), and Andrew Sean Greer (The Confessions of Max Tivoli). And he homesteaded with his filmmaker boyfriend in plush digs at One Fifth Avenue. A charismatic fixture on New York's media scene, Clegg appeared to be publishing's golden boy.

But his crack addiction emulsified him. The hellish cyclone of singed fingers, brute hustlers, emotional bankruptcy, parking-lot sex, white-hot industry gossip, and his failed boutique literary agency, is lyrically chronicled in his new memoir, Portrait of an Addict as a Young Man.

In June 1993, what feels like an eternity ago, I enrolled in an editorial and publishing course in Cambridge, Massachusetts. In the sweaty, hormone-raging dorms, a stone's throw from Harvard Yard, the youngster occupying the room next to mine was a dimpled, mop-top, secretive kid named Bill Clegg. Who could've predicted the afflictions that would later pursue him like furies?

In 2006, fresh from rehab, Clegg re-surfaced at William Morris Endeavor Entertainment, where he still represents prominent writers. Today, Bill, sporting tan cords and a blue polo shirt that accentuates his enormous blue, smoky-grey eyes, floats into DiFiore Marquet, a genteel cafe in the East Village. We discuss his buzzy new memoir, as he munches a beet salad.

Rich Benjamin: How did you come to write Portrait of an Addict as a Young Man?

Bill Clegg: I left the emergency room and psych ward at Lennox Hill Hospital and ended up in rehab in White Plains, New York. When I was in rehab I had a couple of notebooks that a friend who drove me their had given me. I used them to transcribe what I could remember from that two-month period when I was in hotels smoking crack. That period was so dark and intense and ended in a suicide attempt. I regarded that period like a dark dream.

All that stuff came out like a gusher. I wrote not for anything other than to remember. In the same way that one wakes from a nightmare and remembers certain aspects of it, I had a sense of urgency to write it down and to even speak it, so that it didn't disappear.

Benjamin: But what inspired you to actually publish this writing?

Clegg: The decision came later. Re-reading those pages re-acquainted me with how lonely I was, not just as an adult in New York struggling with a crack addiction, but as a kid. I arrived at a point where I wanted to die. But if readers would recognize themselves in my experience, if people could identify with my shame or my embarrassment, then whatever discomfort that I might feel going through the book's publication would be worth it. That's when I decided to have it published.

Benjamin: Of all the book's dramatic episode, which is the most meaningful to you?

Clegg: None is the "most meaningful." I think of it just like one dark episode. So it's all meaningful to me. It was all necessary. It's one big long, dark, sad, destructive, painful episode that led to me getting sober.

Benjamin: How does this book differ from other addiction memoirs?

Clegg: I have no idea, because I haven't really read any of them.

Benjamin: You haven't read junkie memoirs?

Clegg: No, I haven't. And I've read memoirs. I love memoirs. Love them. But for whatever reason I haven't read them. Except for Augusten Burroughs' Dry, which is about his recovery really.

Benjamin: What inspired you to become a literary agent?

Clegg: My former, older girlfriend. I was her parents' gardener and she had tired of publishing and tired of New York. She was always very concerned about what I was going to do in my future. And I believed I was going to stay and be a gardener, landscaper in Connecticut where I grew up. I didn't really have a big ambition beyond that. I read a lot privately. But I never was somebody who talked about what I read with friends.

Benjamin: Then what happened?

Clegg: My ex-girlfriend was like, 'You should go into publishing.' But I didn't think that I'd qualify. After doing an internship at a small publishing house, the first job I was offered was at a literary agency. It was the first job offer I got and I took it. I didn't have a big desire to be a literary agent when I took the job. I thought I was taking a job in publishing, which would probably be for a year or two, and then I'd go back to Connecticut and refer to "My Year or Two in New York," as a lot of people I knew in Connecticut did. They had their tour, then came back, and would refer to that time in their youth living in New York. So when I took the job at Kathy Robbins' agency, she was so brilliant and so engaged with what she did that she made it fascinating. And I was fascinated.

Benjamin: Fast-forward some. During the depth of your crack addiction, I distinctly remember some publishing industry insiders reveled in your downfall -- like ogling a gruesome train wreck. Does that surprise you?

Clegg: Yes.

Benjamin: Really?

Clegg: Yeah. You know, it shouldn't surprise me. But I think each time I bump into something like that--evidence of someone's enjoyment of any painful aspect of my life or anyone's life--yes, I think I'm a little surprised.

Benjamin: What do you think of that Schadenfreude, that perverse pleasure harvested from your misery?

Clegg: I'm familiar with the experience. Certainly, myself, I'm sure I've gossiped about other people's struggles, carelessly and from a distance. So that I understand. But being genuinely joyful at somebody's demise -- I have a hard time occupying that feeling.

Benjamin: After the details of your addiction seeped out and your first agency went bust, how did your clients react?

Clegg: I don't think they can be referred to generally. Each relationship with a writer that I work with or don't work with now is very personal and professional. Whatever stage of repair or disrepair, healing or not healing, every relationship is totally different. Each one is utterly subjective. So I can't refer to the group of them generally.

Benjamin: Having secured a reportedly $600,000 two-book publishing deal and a blizzard of publicity, you are more famous and successful than many of your clients. Does that present any envy or friction?

Clegg: Oh, I don't - I mean, I don't feel like I'm more successful than my clients, artistically or commercially. No, I don't have that feeling. So I don't know how to answer that.

Benjamin: You get better press than many of your clients.

Clegg: Yeah, but a client has a long career. Sometimes there's a season when some people are being written about and a season when some people are not being written about. And some people don't get written about for a very long time. And some people never get written about, but they may be creating brilliant works. My friend has an expression that her father used to use. Today's news, tomorrow's litter lining.

Benjamin: Given your sartorial tastes, Fifth Avenue digs, and upscale lifestyle, many people including myself, always assumed you came from money. But, in fact, your background is more modest. Class-wise, have you been trying to "pass" your whole life?

Clegg: I was always consciously trying to pass, yes. Being in the rooms that I was in--going to dinners and parties where people seemed better educated, better read, and better connected-- I felt I was always just trying to get by, trying to not make a fool of myself, trying to obscure how extreme my different-ness was. Noah [Bill's ex-boyfriend] came from this incredibly supportive, cultured, very well educated family and so every aspect of Noah and his family felt foreign to me. Their kindness to each other, their supportiveness, their fluency in modern art and foreign cinema. So, I felt very much less than, inferior in every way.

Benjamin: You grew up middle-class, in small-town Connecticut--a veritable White-opia?

Clegg: It's a big weekend and summer community in the area where I grew up. The town itself is very tiny. The actual year-long residents were maybe 800 people. The rest came from New York. The only black kids I knew in my class were adopted into white families. I'm sure there were plenty of wealthy black families who went there on the weekends and the summers. But there weren't long-term black households that I was aware of.

Benjamin: Upon first meeting you in 1993, I distinctly remember thinking, "This is the whitest kid in America!" If a Martian descended on New York, how would you describe to them your racial identity?

Clegg: My own racial identity?

Benjamin: Yeah.

Clegg: I'm, you know, a white guy from Connecticut!

Benjamin: Between Stephen, the Asian caterer, Malcolm, the black b-boy, and Carlos, the Brazillian hooker, the volume and texture of inter-racial gay sex in this memoir is titillating and entertaining. Does race ever play a role in your sexual fantasies or preferences?

Clegg: No.

Benjamin: Then tell us about all the sweaty, multi-cultural sex in your past.

Clegg: I'm not very discriminating. I mean race has never been an obstacle or a particular draw. In the book, I sleep with a lot of, you know, white people, too. Anything that made me feel less lonely in the project of smoking crack, whether that was having sex with somebody or watching porn with someone, or just sitting across a couch and smoking the drug and talking, I wanted them nearby. It was a very lonely project. And so, while I wanted to isolate from this whole world that I was leaving, within that isolation I wanted company.

Benjamin: Crack is such a racialized drug. As a crack addict, did you experience your whiteness differently?

Clegg: I was aware that I'm white, yes. I was often times the only white person in the room smoking crack.

Rich Benjamin: In the town where you grew up, crack has very dark connotations.

Clegg: Absolutely. In my hometown, a white woman became a crack addict and ended up having a baby with a black man. The fact that he was black was part of the cautionary tale. That was part of the thunder of that threat. She had gone off to become a crack addict and have a baby by a black man. So, it wasn't a racially evolved town. This was the late 70s, early 80s.

Benjamin: Well, Augusten looks like a garden-variety drunk--no surprise, there. But you don't appear like the media or popular depiction of a crackhead.

Clegg: Yeah, that's really the point. If I don't look like what most people imagine to be a crack addict, that widens the scope of possibility for people of all types to seek help. This memoir is for people who feel so isolated and shameful that they can't even seek treatment.

Benjamin: This memoir coincides with a spike in HIV rates among urban gay men. HIV haunts this memoir like a nameless specter. Weren't you worried about contracting the virus?

Clegg: In all my messy behavior, if there is one thing I was fastidious about, it's safe sex! Always safe sex.

Benjamin: So you're HIV-negative?

Clegg: I'm HIV-negative.

Benjamin: Why did you give your memoir its title?

Clegg: In my memory, Joyce's Portrait of an Artist as a Young Man seems very interested in the shaping influences around the artistic soul. The environment shapes the soul and its expression. And so, I believe that I was born an addict. It occurred to me that this memoir may illuminate the shaping forces around my addictive and alcoholic soul.

Benjamin: The book is obsessed with surfaces and crevices. All those crack hits in swank, boutique hotels. Secrecy and manipulation, and beauty and grime, are pervasive themes. What role do your good looks play in your addiction and in your career?

Clegg: Well, my looks, whatever they are, are subjective. For much of the time described in the book I did not perceive myself to be an attractive person. I've never been confident about my looks. I found it shocking that some articles refer to me as having model-good-looks. It's a lie. If I looked like a model, I'd be one. These references also imply that none of my addiction or success was terribly difficult. Five years sober, I found a comfort in my own skin, grateful for my health and my ability to move through the world on two legs. I think my insides and my outsides have finally sort of aligned in a peaceful way.

Benjamin: I know high-level agents, writers, and publishing execs who just adore you. But I also know well-respected insiders who viscerally dislike you and think you're a mercenary opportunist at best. You've generated a lot of gossip, envy, resentment, and suspicion. How much of that is on your radar?

Clegg: Some of it, probably not all of it. And I think the people around me sort of shield me from it and I certainly don't go looking for it.

Whenever I hear about somebody who's upset about some aspect of me or some aspect of the memoir, it reminds me of a line that Noah always said, "Everyone's fighting a great battle." So my response is to try and be kind to everyone I meet, because each of us is fighting a great battle. I think people who feel so moved or so vexed to gossip or accuse or write cruel things, which they might not even think are cruel, but just true, are very likely fighting a great battle, too. And so, I hope they have good luck with that. Whatever agitation that they have that causes them to do or say whatever they are doing and saying, I hope they find peace.

Benjamin: In the memoir, literature is a sanctuary from your emotional pain. Is that still the case?

Clegg: Without a doubt.

Benjamin: What are you reading now?

Clegg: Poetry. I'm re-reading W.S. Merwin's collection, "The Vixen," which I've read, like, a million times. It's very melancholy. It's very nostalgic. I go back to it like a well.

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