Whenever being a writer wasn't enough to suit his churning sense of drama, Norman Mailer (1923-2007) could come up with some awfully wild-assed ways of advertising himself. They ranged from stabbing his second wife in 1960 (she lived and was dissuaded from pressing charges, and he actually got a judge to buy his argument that being labeled crazy would damage his literary reputation) to running for Mayor of New York City nine years later. But those almost seem like banal versions of Walter Mittyism gone disastrously overboard compared to Mailer's notion that he could become a movie director-indeed, a visionary one, since why else bother if you were him?-without so much as a day's apprenticeship.

Over four decades later, Criterion's Eclipse series has brought out the eccentric results on DVD: Wild 90, Beyond The Law, and Mailer's magna cum gaudy capper to the whole caper, Maidstone, which cured him of his movie mania by busting him financially. To varying degrees, all three of his 1960s bids to make Andy Warhol look like an amateur (yes, that's a joke, kids) are the kind of movie you sit through only in order to have the esoteric pleasure of saying you did. Without a prior interest in Mailer-or, especially in Maidstone's case, a fascination with the 1960s' brew of celebrity, affluence, and apocalypse at once trivialized and transfigured by chic-their value as cinema is close to nil, but things could have been worse. What if he'd decided instead to become the new Dylan?

Because Mailer also stars in all three, their main fascination is that they're a real-world equivalent of Terry Southern's fantasy of a middle-aged Jean-Paul Sartre taking it into his head to not only write but dance the lead role in a ballet. In his collection Red-Dirt Marijuana and Other Tastes, Southern imagined a cowed le tout Paris saying "Il ne danse pas mal, Jean-Paul." Not without cunning, Mailer avoided le tout Manhattan's perhaps less charitable reaction by enlisting several of its luminaries as participants-above all, George Plimpton, who pops up impersonating the mayor of New York City in Beyond The Law. Even more than Mailer's own presence, which is saying something, that certifies we're watching a trio of time capsules.

Wild 90 literally began as a party game. After performances of Mailer's play The Deer Park in 1967, the author and a couple of cronies used to unwind in a Village bar by pretending to be a Mafia princeling and his henchmen. (What this says about the cronies is a rock perhaps best not turned over.) Then Mailer, never one to suppose his shenanigans could ever be mere shenaginans, got the bright idea of hiring none other than D.A. Pennebaker-as in the Dylan doc Don't Look Back-to film them doing their thing. To provide some semblance of a dramatic situation, they're all supposedly holed up in a room during a gang war.

Murky and interminable, the movie is pure hell to force yourself to keep attending to for more than a few minutes at a time. My own thoughts kept drifting to the Saints' Super Bowl prospects and the death of Phyllis Diller. For long stretches, we might as well be trapped in a freight elevator with three grating drunks under the impression they're hilarious, and Mailer-who comes on like Huey Long trying to be Robin Williams, not the combo of anyone's dreams-only qualifies as the thing's director in the sense that a landlubber who buys a yacht might award himself a commodore's cap.

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He isn't staging the action, deciding the camera's moves, or guiding any of the performances-except his own, of course, with what looks like a hefty amount of inspirational help from bourbon. ("Un film de Jack Daniel's" would be a much more accurate directorial credit.) Even when it came to shaping this witless material in the editing room, his technical cluelessness-and, according to Pennebaker, disdain for what he thought was scut-work-left him relying on hired hands.

Beyond the Law is more ambitious. Now that he'd gotten the bug, Mailer cast a whole slew of his friends as cops and perps getting through what was supposed to be a typical night in a New York police precinct's interrogation rooms. This time out, his basically lazy notion that putting amateurs in unscripted situations might get unconventionally vivid effects does pay some modest dividends. There are bits of behavior and faces caught on the fly that have a quasi-documentary plausibility. But they don't add up to anything, because we haven't been given a good reason to care who any of these people are and the sequences don't link up or build on each other.

Tellingly, the only two scenes likely to pique anybody's curiosity each reveal the whole cinema verité conceit as a self-indulgent stunt. When Plimpton shows up, his and Mailer's mutual amusement clearly has nothing to do with the people they're pretending to be-and that's fine with us, because who they were is infinitely more interesting. The long episode of marital discord that gets sprung on us at the end – Norman and his real-life fourth wife sparring in a bar-plays like a desperate, exhibitionistic bid to yank the movie we've been watching so far back from the precipice of being utterly pointless, but it does have a queasy-making zing.

Maidstone, by contrast, is by far the most watchable of Mailer's movies. That isn't because it's any good, exactly, but because it's a remarkable document-and not only thanks to the fabled brawl between Mailer and Rip Torn that provided its unexpected conclusion, either. As an only partly intentional depiction of how the late '60s went off the rails, it's almost as evocative as Gimme Shelter, albeit with much worse music and a tubbier star performer.

Mailer plays Norman T. Kingsley, a world-famous cinema auteur-fat chance-who's contemplating running for President as he films a movie about the studs and clients in a male brothel. Meanwhile, a hush-hush government outfit is considering whether to liquidate him. As silly as the whole convergence of paranoia, vanity, radical chic, and upscale debauchery is, just watching all these privileged folk cater to Mailer's fantasy of being a one-man Zeitgeist-everybody from Hamptons richies to boxer Jose Torres and assorted literati-makes for a memorable record of the period's nutso streak. That's especially so since affluence and fun are this ostensibly sinister-minded movie's unstated but omnipresent givens.

Unlike its two predecessors, Maidstone also sticks in the mind. It did in mine, anyway; I first saw it in my teens, one of a lonely handful of Mailer enthusiasts during its fleeting run at Washington's old Biograph theater. Watching it again decades later, I was surprised at how its peculiar atmosphere and mood had stayed with me. That was more than I could say for my adolescent infatuation with all things Mailer. Yet if his sheer preposterousness is likely to loom larger for later generations than his literary gifts-except, perhaps, in Armies of the Night, when they worked hand in hand-that's partly because a culture that could not only accommodate but be nourished by his brand of craziness has gotten a lot harder to imagine.