Of the various places I’ve visited that are associated with Alexander the Great, two stand out in memory. Siwah Oasis, an astonishingly large and verdant depression in the Egyptian Sahara near Libya, contains the ruined temple whose oracle, world-famous in ancient times, reportedly revealed to Alexander his divinity as well as secrets that so stunned him that he asked to be buried there. When I was in Siwah in the early ’90s, a European film crew was there investigating persistent rumors that Alexander’s body, which disappeared somewhere between Babylon and the Sahara, had actually made it to the oasis and is hidden there now. Though the crew evidently didn’t find the prize it sought, Siwah seemed to me haunted by the presence of what might be called the Egyptian Alexander–a hero-warrior touched with the divine, whose superhuman exploits would echo through the ages. In Iran, the ruins at Persepolis suggest another face of the same man. Though only grand fragments of the legendary palace complex of Persia’s kings, they dwarf all surviving Greek ruins and, in so doing, indicate the sophistication and splendor of the sprawling empire that Alexander conquered in a blitzkrieg campaign. Supposedly, the Macedonian king destroyed Persepolis by torching it, in a notorious incident of cultural vandalism. To this day, Iranians see Alexander not as a hero but as an invader, a destroyer, a horned devil.

Between this demonic Persian Alexander and his divine Egyptian double, you have a vivid diagram of the extremes which seemingly characterized the actual man. Some have described him as a visionary idealist who foresaw a world where tribal and cultic divisions would be transcended. Others see him as an obsessed and cruel tyrant willing to sacrifice his own people in an insane quest to conquer the entire world. There is, of course, no reason we should feel obliged to choose between these two visions, since together they give us something of the outsized and highly combustible complexity of Alexander’s recorded personality.

Given that movies dote on extreme personalities, Alexander might seem an ideal subject for screen treatment. But ideal does not mean easy, and Oliver Stone fans as well as Alexander aficionados–I am both–must now ponder the reasons why Stone’s $150-million, nearly three-hour Alexander is likely to be regarded as a disappointment by both groups (and perhaps worse than that by folks who care for neither the director nor the conqueror). Did Stone fail Alexander, or was it vice versa?

I don’t mean to imply that this is a shabby epic by any means. The production is handsome and sweeping–Stone put all that money up on the screen–and the director’s sure craftsmanship remains evident throughout. Yet the film, in effect, places history above drama, as well as meticulousness above cinematic daring, which results in a couple of singular deficits: We’re never given a compellingly (re)imagined vision of the corner of the ancient world Alexander inhabited, nor, more crucially, a vivid and convincing portrait of the man himself.

The latter fault involves a number of miscalculations in the screenplay, the most symptomatic of which I call the Big Gap, a leap in the narrative that comes less than an hour in. The tale begins with some unfortunately typical clunky exposition as Ptolemy (Anthony Hopkins), one of Alexander’s former generals, recalls the leader decades after his death. From here we flash back to Alexander’s youth, with episodes that include the boy’s taming of the horse Bucephalus, his schooling by Aristotle and his budding romance with Hephaistion, who will become one of his generals. But most of the emphasis here goes to the fraught relationship between Alexander’s ambitious, controlling mother Olympias (Angelina Jolie, who gives the film’s best performance) and her volatile husband, Philip II (Val Kilmer). Alexander, plausibly enough, is caught between his parents’ competing agendas, as we see in a scene when, at 19, he objects to his father’s marriage to a second wife.

From this episode the film leaps directly to the battle of Guagamela, the third of Alexander’s major engagements with the Persians and the one in which he effectively conquers their empire. The Big Gap between these scenes is only six years (roughly 337-331 B.C.), and later we see that the elision is used not only to condense the story but also to withhold a dramatic pivot: Late in the film when Alexander’s plans have begun to unravel, we flash back to 336 B.C. and the murder of Philip, in which Olympias probably and Alexander possibly were complicit.

As a narrative strategy, this gambit has an obvious rationale. Yet it deprives us of something critical: a sense of Alexander as a flesh-and-blood daredevil and charismatic commander. The real man was not only a brilliant tactician, after all, but a phenomenal fighter who led by example, battling hand-to-hand at the head of his troops, outdoing even the most skilled of his warriors in the physical ardors of combat. Alas, this Alexander is MIA in Alexander. In skipping past the years when Alexander first gained the allegiance of his troops, subdued the Greek city-states, crossed the Hellespont and ignited his campaign of world conquest, Stone gives us a hero whose battleground heroism is stated rather than shown, assumed rather than viscerally demonstrated.

This would seem curious in a director known for his martial physicality, but it reflects a decision that presumably was as deliberate as it is misguided: Stone determined that Alexander’s most important relationship was with his parents rather than with his men. Ironically, this approach reminds us of why Born on the Fourth of July (with its Oedipal acting out) is a weaker film than Platoon (where psychology belongs to the battlefield). Granting that the film’s account of the Philip-Olympias tangle may be accurate historically and psychologically, we are still left with a drama that calls to mind too many dysfunctional-family cliches, and that’s muddled even on its own terms: Just prior to Philip’s murder Alexander seems to know something’s coming, but then acts shocked and surprised when it does. So which is it? Paradoxically, Stone’s attempt to give Alexander a believable psychology deprives him of that very thing, even as it simultaneously robs him of outward valor and force.

Colin Farrell, an excellent actor in many circumstances, ends up defeated by Stone’s conception and writing of Alexander. Donning one blond wig after another (coif-wise, he goes from Elton John to Mia Farrow), Farrell seems a bit lost in his performance, as if unsure how to connect with a character so distant in time and sensibility.

Granted, this is a challenge for audiences and actors alike. After 2000 years of Christian prudery, for example, it’s no easy task to connect with antiquity’s ideas of sexuality. But here again, Stone is guilty of telling rather than showing. We hear the ancient witticism that Alexander “was never conquered, except by Hephaistion’s thighs,” yet those thighs are kept demurely off-screen; while Alexander’s relationship with Hephaistion (Jared Leto, wearing a ridiculous amount of eyeliner) is reduced to hugs and longing looks, the conqueror gets physical only when he encounters princess Roxane (Rosario Dawson), whom, in actuality, he was presumed to have married to cement an alliance with the Sogdians.

The choices just described illustrate some of the key problems of Alexander. Stone no doubt thought he was being daring in portraying Alexander’s quote-unquote bisexuality, and in context perhaps he was (recall that Troy converted Patroclus into Achilles’ “nephew,” and a now-shelved competing Alexander project was rumored to make its hero a proper heterosexual). Yet Stone’s means of implementing his decision is so cautious, so lacking in physical and emotional credibility, that it ends up negating its own intrepid intent.

To an extent, the director’s difficulty with the ancient milieu is unsurprising. I’ve always thought that Stone’s phenomenal instincts as an artist are akin to those of actors who depend on sense memory. With his kinetic sense of camerawork, film stocks and so on, he can brilliantly conjure up a moment in history–as long as that moment belongs to his lifetime. Alexander is the first film he’s ever made that’s set before his own birth, and it shows him relying less on his own imaginary resources than on that most dubious of allies: research.

And that’s not enough. Perhaps more than any other genre short of sci-fi, ancient-world movies need real visual daring, whether it be in the direction of exuberant pulp like Jason and the Argonauts or a truly artistic hallucination like Fellini Satyricon. Alexander‘s expensive but standard-issue visual approach, in unhappy contrast, recalls the staid, ponderous, by-the-book Hollywood sword-and-sandal epics of yore, and it reminds us why those films were so undistinguished back then: They invariably failed to summon a feeling of real strangeness and difference.

In this case, it’s not that history doesn’t provide the basis for a more idiosyncratic vision. Recent writers, for example, have made much of Alexander’s huge problem with alcohol. He was roaring drunk, apparently, when he killed his friend Cleitus, and, by some accounts, when he torched Persepolis–an incident that surprisingly isn’t in the film. Oliver Stone, of all directors, should be able to do something creative with substance abuse problems, no?

I’m not just suggesting that his Alexander needed to be drunk(er), but also that the movie itself could stand the same. Indeed, stylistically, there’s only one passage in Alexander–a climactic battle where infrared film suddenly turns the drama into an acid trip–where we unmistakably know we’re in an Oliver Stone film. But it’s too little, too late.

To put this in a way that both Stone and Alexander himself could understand: Alexander turns out to be the director’s most earnestly Apollonian film. It should have been his most dangerously Dionysian.