Terry Southern: hipster doofus or literary innovator? His qualifications for both positions have always been in question. Two new books — one a succinct, long-overdue biography, the other a collection, edited by Southern’s son, of magazine articles, Saturday Night Live proposals and lost tales — reveal the duality of desires that made the late author so promising, and so disappointing.

Southern has always been a tough read. It’s not that his scathing screenplays (Dr. Strangelove, Easy Rider, The Cincinnati Kid), nefariously funny magazine work (like his infamous Esquire coverage of the 1968 Chicago Democratic Convention) or his multitude of strange, sardonic stories (The Magic Christian, Candy) are difficult to absorb. Far from it. The subterranean Texan’s finest moments are exquisite reads, plump with anti-idealism, anti-sentimentality and a wit that explodes cultural myths at every turn. His was a candid Quality Lit (his term — Southern was always good for abbreviation) written with an unsympathetic eye and without regard for guilt, pity or (until the latter part of his life) autobiographical shadow. Self-examination, yes — an unraveling that’s still rapturous in its Möbius strip acuity. But little to tell you who he was within the work. And, ultimately, little to tell you how he allowed it to slip away.

Southern’s coolly detailed expressionist stance made him a harbinger of New Journalism — as witnessed in the Now Dig This tales like "When Film Gets Good" and "Fiasco Reverie." Enamored of post-Lost Generation types like Faulkner and Henry Green — two truly absurd writers he came to befriend, among so many others — Southern’s work had a naturalistic surface, an open, honest naïveté with nightmarish undercurrents. At its most cunning, his explosive but lyrical grotesquerie was like a hot poker in the eye of conventional narrative.

Like Beat pal William S. Burroughs, Southern wrestled with how to bring writing into the future. His latter prose — like 1968’s "Grooving In Chi" and "Wormball Man" — grows ever more monstrous, filled with Steadman-ish caricatures, that, once bloated with psychedelic bonhomie, seemed on the verge of floating away.

Southern’s grandness of ego, his hip radar — that which guided the high-society rouse of Christian and the titillating Candy, the satirical farce of Strangelove and The Loved One — was the very thing that came to make blunt his life and work. In Paris and Greenwich Village in the ’50s, he was an impoverished writer. In the ’60s, he jetsetted through New Hollywood and Mod London, effervescently taking over boardrooms and brothels, dazzling directors and society doyennes with his mad tales. He was as generous with his money as he was his words. He lived life amongst literature’s greats and cinema’s sexiest. He enjoyed the rock-star lifestyle with the Rolling Stones, intellectual pursuits with Nelson Algren and film chats with Stanley Kubrick. Who wouldn’t succumb? His ribald sense of humor, with its penchant for excess and repulsion, took him over. For all Southern’s failings, in the latter half of his life, he still managed bittersweet works — like the fond "Remembering Abbie," included in Now Dig This — and too-clever-by-half interview sessions about the strange, unregrettable trip that was his life.

Hill does not spare or spoil Southern. He is as enamored by his subject’s magnificence as he is appalled by his decline, pondering how a man allowed himself to be swallowed up by the very things he lampooned in his work. Yet there is no judgement on Hill’s part. Instead, his complex yet fast-paced road map of the cerebral and the celebrated sets us up nicely for the very grand stories that made Southern America’s most finely tuned — yet least appreciated or understood — comic mind.

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