WAG: You were friends with Terry Southern in his last years. Did you (and he) know at the time that you would write a biography about him? And did the older person you met seem all that different from the young man you write about in the early chapters of A Grand Guy?

Hill: The biography and my friendship with Terry began when I interviewed Terry by phone and post for Vox, a magazine I was editing in 1990. My first attempt at an interview was a disaster. Terry was quite shy when first meeting or speaking to strangers. However, we kept in touch even after a brief interview was published.

My first notion of the book was of a Hitchcock / Truffaut style book-length interview. By 1993, a more formal biography made more sense. The bulk of my interviews with Terry were done that year at his Connecticut home. He also gave me unmediated access to his personal papers—a courtesy extended by his son, Nile, after his death.

As for the manner in which time changed Terry, I would have to say it was only his health that really got in the way of his curiosity, humor and intelligence. Before I first met Terry in person, I had this misguided panic attack-like fear I would meet a drug casualty (I had just seen this documentary on John Phillips). Instead, I met a very sincere and sensitive person with immense gifts. He loved meeting people, wrote all the time and was extremely hospitable. Having talked to some of his screenwriting students, I know Terry had an enormous influence on their own sense of artistic values.

I don't want to suggest that Terry was without flaws—business naivete and career hubris being the chief ones—but I think I am not alone in thinking he was, in many respects, a kind of Hemingway figure for those of us who came of age in the Sixties and Seventies.

WAG: Southern's professional career covered a lot of ground. As he matured, he went from writing short fiction for "little" magazines to writing novels for "little" publishers and then from writing screenplays to writing skits for Saturday Night Live. How do you primarily think of Southern-as an artist in print or an artist on the screen?

Hill: I think Terry was an extremely gifted novelist and short story writer. For me, The Magic Christian is a landmark novel as important and unique as The Great Gatsby and The Sheltering Sky, while the short stories in Red Dirt Marijuana are as good as anything contemporaries like Cheever, Capote or Shirley Jackson wrote. 'You're Too Hip, Baby' is arguably more significant now in this cooler-than-thou age than it was in the Fifties. His screenwriting via Dr. Strangelove and Easy Rider ( as well as underrated films like The Loved One, Barbarella and End of The Road) has influenced writers as varied as Bruce Wagner and Whit Stillman.

However, I think Terry's film career is also a cautionary tale for screenwriters. Terry always said, "Screenwriters only have the power of persuasion." He knew it was a director's game. Post-1970, Terry got involved in more than one project at a time to deal with financial pressures. He abandoned writing novels and short stories. The irony is that Hollywood has a perverse respect for literary writers, and it is my belief if he had maintained a steady Quality Lit output he would have had more leverage. However, by devoting almost all his energy to screenplays and treatments, Terry became simply another dues-paying WGA member who could be hired and fired at will. Still, Terry wrote some very good screenplays in the Seventies and Eighties—A Cool Million, Junky, The Hunters of Karin Hall and Grossing Out—which deserve a second look.

Steven Soderbergh, are you listening?

WAG: In an unpublished interview with The Paris Review, Southern said that "[T]he important thing is to keep in touch with the youth of whatever culture you're in." Do you think his shift to screenwriting was indeed a necessary move into what he considered the Sixties' most important medium? Or did it, from the privileged perspective of history, lead him astray as an artist?

Hill: Like a lot of writers, Terry loved the medium of film because of its immediacy. He was fortunate to work with a number of talented directors--Stanley Kubrick, Tony Richardson, Roger Vadim, Norman Jewison, Jerry Schatzberg, etc.—whose careers were also boosted by the hothouse excitement of the Sixties. It was a boom time for filmgoers. Audiences seemed to be open to anything from Godard or Third World cinema to the pre-Hollywood New Wave represented by films like Psycho, The Manchurian Candidate, Midnight Cowboy, etc.

In retrospect, the 1969 release of Easy Rider seems to be a watershed for Terry. Neither he, Hopper nor Fonda seemed to be able to capitalize on the success of that film. Hopper and Fonda did reap the financial benefits, but it took over a decade for Hopper to shed his personal demons, and Fonda never really seemed to find a follow-up role as actor or producer (although he is amazing in The Limey).

Despite the fact that Easy Rider made it easier for Coppola, Scorsese, Spielberg and the other young turks of yore to take over the studios in the Seventies, Terry, for reasons I am still not able to fathom, did not get a chance to work with these directors. Then again, the Hollywood New Wave of the Seventies was very auteur-conscious, whereas the slightly older generation of Kubrick, Jewison, et al. were much more conscious of the primacy of a solid screenplay. Still, it would have been great if Terry had gotten Blue Movie made with Mike Nichols.

The ultimate solution to getting screenplays past the development stage is going the low-budget indie route. I think we forget in this Sundance age of ours how rare and difficult it was for screenwriters to do this in the Seventies. I also think Terry was too nice to make the necessary translation from screenwriting to direction. You have to be a Commander General to succeed, and I think Terry was more of a kindly King Arthur type, if you will pardon the mixed metaphors.

WAG: Considering Southern's talent as both a fiction writer and a screenwriter, it's hard not to consider the last fifteen years of his life as sadly unfulfilled artistically. Did you ever ask him how he sized up the arc of his career?

Hill: Yes. Terry told me quite simply that if he thought there was anything to be gained from dwelling on his failures, he would do so, but since there wasn't, he just plowed on. Terry wasn't given to self-pity.

I suppose it is a weakness of the latter part of my book that I don't get across how much fun Terry had. He had friends from many walks of life. He had a larger-than-life take on things that transformed the most banal conversation into something special. Terry gave a lot to people through his essentially generous personality. He had a genius for friendship.

In cold careerist terms, Terry's life may seem wasted, but the books and films continue to resonate. In the end, it is the quality of work that separates the Terry Southerns from the Robert Ludlums. I don't mean any disrespect to a certain kind of well-paying escapist writing, but if you are a young writer who takes his or her work seriously, who would you rather emulate?

WAG: You note in the book that George Plimpton sometimes thought of Southern "as a painter whose work is briefly in vogue and then forgotten as the times change." On the other hand, Grove Press has re-issued nice editions of five Southern titles, and a special edition of Dr. Strangelove was released on DVD in March. On the surface, the Southern legacy would seem to have some legs to it. How do you think Southern is viewed today-and how do you think he will be viewed in the future?

Hill: I am fairly certain Plimpton meant his comments to be taken as an explanation of how writers move in and out of fashion and not as a comment on Terry's work.

One of the things that sustained me through the long road of writing and finishing a biography (not to mention finding a sympathetic publisher) was that I knew it would bring about and sustain a renaissance of interest in Terry's life and work. When I started the book, little had been written about Terry since 1970. Since Terry's death in 1995, there have been the Grove and Bloomsbury reissues, several magazine articles, and in the last few months, things like Strangelove and Candy on DVD (I love DVD...it forces people to look a things a second, third and fourth time...may it turn a whole generation of couch potatoes into Cahiers Du Cinema types. 'Hey, honey, let's listen to the director's commentary one more time?'). A new collection, Now Dig This, edited by Nile Southern and Josh Alan Friedman, comes out in late May from Grove. There are also other projects in development including an amazing spoken word CD which unites Terry with the likes of Jonathan Winters, Martin Mull and Sandra Bernhard.

While Terry's specific tone and sensibility are impossible to replicate, I think his pioneering brand of satire is just too irresistible to each new generation of iconoclasts to avoid. In some way, the present is just like the Fifties were in the way the establishment via multinationals sets the agenda for cultural discourse. We are beginning to see a new wave of protest via books like Naomi Klein's No Logo to counter the tyranny of the mass media and prepackaged Hip.

Terry's targets—the bureaucratic, military, business, scientific establishments—haven't disappeared. They have just gotten more sophisticated at manipulating power. So if anything, I think we need Terry Southern and other voices like him more than ever.

WAG: Of the writers working today, who do you think comes closest to Southern's voice and world view?

Hill: That's a difficult question to answer without sounding like an armchair quarterback. I don't think there is anyone exactly like Terry out there. I can only speak about what I currently find funny or similar. I have a fondness for humorists like Christopher Buckley (even though he's a conservative, he doesn't have the knee-jerk frathouse instincts of PJ O'Rourke) and Steve Martin in The New Yorker. Emily Prager's novel, Eve's Tattoo, is an underrated social satire that shares the ambition of Southern's brand of outrage.

Since we are all obsessed with the media these days, it is not surprising that the most successful films and television in recent years play off the hall of mirrors we find ourselves living in. Larry Sanders, The Player, Fight Club, American Beauty, Being John Malkovich, Three Kings, There's Something About Mary (Cameron Diaz is very Candy-like in that film) and Election all have Southern-like aspects to them. They certainly force viewers to think about what they are watching.

Terry was always optimistic, and I think we owe it to ourselves not to become too cynical about the barrage of media garbage that seems to inform our culture. Ultimately I think that is what Terry's brand of Hip was all about—you can't take people or life for granted. Cynicism is just as destructive as blithe smugness. You have to aspire to something grand even when you don't feel like it.