Jake des Esseintes’s review published on Letterboxd :
It's sort of amusing, and maybe ironic, that at least up until Marjorie Prime this was probably Michael Almereyda's most well-known and widely-seen work (I even remember my old neighborhood Blockbuster Video having a poster for it hanging in the window for what seemed like years). On one level, it makes a certain amount of sense, after all William Shakespeare is a recognizable and, it seems, endlessly bankable property, and in turn the film attracted a cast of actors far more well-known than any of the director's previous films: Kyle MacLachlan, Sam Shepard, Bill Murray, Julia Stiles, and of course Ethan Hawke at the height of his popularity in the titular role. And yet, I imagine, that to fully appreciate the film or even to understand what Almereyda is trying to do, one needs to place it within the context of the director's larger body of work.
Updated, quote-unquote postmodern Shakespeare adaptations were sort of a trend for a while in the late '90s/early '00s. For those too young to remember, there was Baz Luhrmann's Romeo + Juliet starring teen heartthrobs Leonardo DiCaprio and Claire Danes, or Tim Blake Nelson's decidedly less successful "O" (as in Othello), in which Stiles also appeared, alongside Josh Hartnett. At first glance, Almereyda's adaptation of Hamlet might seem to be a film in a similar vein (as surely the producers who funded the film might have liked), but in fact the director is interested in something very different than merely updating the Bard for the MTV age (despite the unfortunate sight of Stiles' giant JNCO skater pants). Nor is Almereyda, generally speaking, particularly interested in being cutely "postmodern", or at least not in the same manner as his peers.
No, rather Almereyda approaches Hamlet as a Termite Artist's greatest challenge (and lest you think I'm over-stressing this point, Almereyda literally befriended, and was mentored by, Manny Farber, the author of "White Elephant Vs. Termite Art"). Where most directors tend to use Shakespeare as the ultimate excuse to let their inner White Elephant run wild (think of Lawrence Olivier, or Kenneth Branagh, or even Peter Greenaway... as great of a film as Prospero's Books may be, "termite" in approach it most definitely is not), Almereyda approaches the material playfully, as an exercise in stealth auteurism while remaining simultaneously faithful to the material. He isn't so much "subverting" Shakespeare as he is... adapting Shakespeare to make what is unmistakably a Michael Almereyda film.
Perhaps only Derek Jarman, and arguably Orson Welles, ever attempted to do quite what Almereyda is doing here, and not as successfully if I might say so myself (Godard's King Lear is great, but it's really a whole different thing. There isn't much actual Shakespeare in it, for a start.) Although his faithfulness to the text prevents the film from being quite as playful or fun as his previous genre deconstructions like Nadja or The Eternal, it operates on very much the same level. There are moments, perhaps, where Almereyda can't resist being slightly too cute with his anachronisms (Hawke reciting the "to be or not to be" soliloquy in the "Action" aisle of a Blockbuster Video, while a scene from The Crow: City of Angels plays on the screens behind him no less). But largely he succeeds in demonstrating the durability of the original text while forever gnawing away at its foundations.
This is one of the main reasons I noted above that the film probably benefits significantly from first being familiar with Almereyda's larger body of work, as one is then better able to appreciate the ways in which he puts his distinctive auteurist stamp on the material. Note, for example, Hamlet's Pixelvision camera, which is to say, Almereyda's. I wouldn't begrudge a viewer for failing to pick up on such self-reflexive gestures. In fact I'm nearly certain that this was the first Almereyda film that I saw, as I suspect was the case for many viewers. This is why I say that it's sort of ironic that this ended up being his most widely-seen work. To be fair, not that Almereyda would probably care much. Being the termite he is, I don't think he's overly concerned with whether one immediately detects his directorial fingerprints or not, but I can assure you they're there.
On another level, one could probably simply enjoy this film as a chance to see Shakespeare performed in an arch style roughly equivalent to Almereyda's contemporary Hal Hartley (I wonder if the bold block lettering announcing the film's title aren't an indirect homage to the director with whom Almereyda has often shared cast members). If, for instance, you've ever wanted to see Kyle MacLachlan in a Hartley film as much as I have, this is about as close as we'll probably ever get (or, you know, you could just watch the first season of Twin Peaks I guess). Being the ever-adaptable termite that he is, Almereyda is a marginally less rigorous stylist than Hartley, ever so slightly more willing to shoot conventional coverage, but the similarities are most definitely there (in fact, I rewatched this part of the way through Flirt because I needed a break but wanted something similar, so take that as you will.)
Or, I suppose, one could simply enjoy this as a strange artifact of late-'90s fashions (see again Stiles' ridiculous JNCO pants). As Almreyda himself admits, his intention was to make a version of the play specific to the exact moment it was made, and were he to make it now, it would be by its very nature a completely different film. And yet, for all its baggy raver gear and now-closed video chains, the film's vaguely eerie, pervasive sense of media saturation amidst an alienating, techno-futurist, multinational-conglomerate world of steel-and-glass architecture by and large doesn't feel particularly dated. Not unlike Olivier Assayas' Demonlover, one might even say that it feels oddly familiar (incidentally, the critic Charles Taylor mentions both films in his seminal essay on Millennial, globalized cinema, "Lost at the movies").
Almereyda would expand upon this vaguely techno-futuristic sensibility in his follow-up film Happy, Here and Now, but the groundwork was already being laid here. The portable video-editing device Hawke's Hamlet is seen using might appear a bit quant and antiquated from today's perspective, but his constant mediation through tiny screens isn't. Yet crucially, as in Almereyda's next film, the shiny, new world of the Denmark Corporation is foreboding, sure, but it isn't quite a spiritual vacuum. One of the videos Hamlet is seen watching is a moving speech by the Dalai Lama (that he's saying something about "to be..." is undoubtably a significant reason for why Almereyda includes the clip, but that doesn't negate its poignancy). In these films, technology is alienating, but it still leaves room for hope and connection, both spiritual and emotional.
This is perhaps why the film, despite the inherent "postmodern" playfulness that results from self-consciously transposing Shakespeare into the present day, Almereyda nonetheless manages to preserve the emotional core of the text more or less intact. It may be arch and "ironic", yes, but it isn't insincere. Baz Luhrmann might not have been insincere either, but his inherently overbearing, camp mentality can only reduce Shakespeare to the level of kitsch. Almereyda, on the other hand, as irreverent as he may be, preserves the fundamental meaning of the text and revitalizes it. He doesn't merely update Hamlet for a "hip" young audience. In the spirit which Ezra Pound meant these words, he makes it new.