Victim of the Sexual Revolution.

Terry Southern's telling trip from hipster to has-been

Just how cool was the writer Terry Southern in the 1960s? That's him on the cover of Sgt. Peppers, for God's sake, sporting Italian shades and flanked by the likes of Lenny Bruce, Marlon Brando, and W.C. Fields. As journalist Lee Hill makes clear in his engaging and competent biography, A Grand Guy: The Art and Life of Terry Southern (HarperCollins), the '60s were relentlessly good to Southern, best known today for his screenwriting work on Dr. Strangelove, Easy Rider, and other signature films of the decade.

His success was a long time coming. After serving in Europe during World War II, Southern developed a minor reputation in the '50s as an occasional contributor to acclaimed small mags such as Paris Review and the Evergreen Review, as the author of the wicked novel Flash and Filigree (think Nathanael West in an L.A. plastic surgery office) and, most notably, as the coauthor of Candy, a notoriously banned "db" (dirty book) published by Maurice Girodias' legendary Olympia Press (the same Parisian house that originally put Lolita and Naked Lunch into print).

It was only in the '60s that Southern, already approaching middle age in a decade that fetishized youth, fully came into his own as a countercultural hipster. By penning darkly subversive novels such as The Magic Christian and screenplays for films such as Dr. Strangelove, he helped to create an America energized by newfound sexual liberation, urbane coolness, and casual iconoclasm. Indeed, though he is largely ignored today, it is tempting to say that he was the dominant American writer of the decade. Certainly no other author playing at what Southern sarcastically referred to as the "Quality Lit Game" managed to have more simultaneous critical and commercial success in fiction, journalism, and, above all, screenwriting.

The '60s saw the American publication of The Magic Christian, which had appeared earlier in England to rave reviews; the above-ground re-release of Candy, the smart and smutty update of Candide that went on to become a massive bestseller and cultural touchstone; and highly regarded reportorial forays for Esquire and other glossies. (His "Twirling at Ole Miss," an absurdist account of campus life at the University of Mississippi, remains one of the seminal texts of what later came to be lionized as the New Journalism.) As the cowriter of films such as Dr. Strangelove, The Loved One, Barbarella, and Easy Rider, Southern seemed to be at Ground Zero of almost everything that was happening.

Though the film versions of Candy and The Magic Christian were massive flops, they were the sort of star-studded failures--each featured appearances by the likes of Marlon Brando, Ringo Starr, Richard Burton, Peter Sellers, James Coburn, Anita Pallenberg, Roman Polanski, and Raquel Welch--that bolstered Southern's reputation. He closed out the decade with the archly decadent novel Blue Movie, which chronicles a legitimate film director's attempt to make a porno flick with A-list stars and top-rate production values.

Then it was essentially all over for Southern, his success ending as abruptly and definitively as the race to put a man on the moon. Though he would live for another quarter-century, dying from respiratory ailments in 1995 at the age of 71, he would never again come remotely close to the success--or cultural relevance--he enjoyed during the '60s.

As sympathetically depicted by Hill, those final years were painful, steeped in humiliation and desperation. They also present a literary mystery: What could have possibly happened to Southern's estimable talent? In different ways, Hill's book and a wide-ranging and uneven collection of Southern's writing, Now Dig This (Grove Press), edited by Southern's son Nile and Josh Alan Friedman (the son of Southern's fellow "black humorist" Bruce Jay Friedman), provide intriguing answers to that depressing question.

Southern spent the last two-and-a-half decades of his life writing self-parodic drivel for National Lampoon (Now Dig This includes several examples, including a once-famous but poorly aged bit about necrophiliac Vietnam vets); failing miserably as a writer for Saturday Night Live ("the worst [job] I've ever had," he said of the experience); and pursuing unlikely film projects (including a doomed adaptation, of his friend William Burroughs' memoir Junky involving Easy Rider partner Dennis Hopper).

The only large projects Southern managed to complete during his last 25 years were the execrable 1988 movie The Telephone, which was written with the musician Harry Nilsson and starred Whoopi Goldberg as a crazed actress, and the maudlin 1991 autobiographical novel, Texas Summer.

So what happened? Southern was undone by a number of factors: His fondness for booze started to catch up with him. He managed his money poorly and found himself in chronic trouble with the Internal Revenue Service. The money problems in turn encouraged him to make bad choices in pursuit of cash.

His abiding interest in film robbed him of his creative independence. In an early '60s essay in The Nation included in Now Dig This, he contends that "it is not possible for a book to compete, aesthetically, psychologically, or in any other way, with a film." But film is inherently collaborative, artistically and especially financially, and Southern had bad instincts when it came to picking projects and partners that would pay off. Even as movie deal after movie deal fell through, he didn't have the discipline or confidence to write novels over which he would have exercised something like complete control.

As important, Southern's predilection for metafictional conceits fell out of literary favor; as Robert Rebein argues in his new study, Hicks, Tribes, and Dirty Realists, the postmodern irony that infuses books like Candy and The Magic Christian was "absorbed" into a "new realism that is more or less traditional in its handling of character, reportorial in its depiction of milieu and time, but... [also] self-conscious about language and the limits of mimesis."

Most profoundly, Southern became a victim of the cultural revolution he helped instigate. One of his signature flourishes was the shocking sexual innuendo, and he never tired of it, even after America ceased to be scandalized, or even titillated, by such antics. It may have been risque to name the president Merkin Muffley in 1964's Dr. Strangelove, but by the end of the decade, even the premise of Blue Movie was bordering on passe.

Yet Southern kept at it, with increasingly puerile and dated results. In the end, he had the rotten luck to outlive, but never quite outgrow, the sexual revolution he helped inspire.

Nick Gillespie ([e-mail]) is REASON's editor-in-chief. A version of this appeared in the July 1 edition of the Washington Post's Book World.