Off the Deep End — Poolman

William J Hammon
9 min readMay 23, 2024


Every once in a great while, a film comes along that is so bad, so poorly made, so bafflingly offensive, banal, and misguided that the sheer mass of terrible collapses in on itself like a neutron star and creates a spectacle so ironically joyous that the viewer ultimately has no choice but to submit to it and somehow fall in love, achieving a quasi-nirvana where he is fulfilled by its emptiness on a level that cannot be quantified. I’m talking Mac and Me, Freddy Got Fingered, Howard the Duck, or the true masterpiece of “so-bad-it’s-good” art, The Room.

So naturally, when I heard last year that critics and audiences at the Toronto Film Festival hated Chris Pine’s directorial debut, Poolman, so much that they walked out of the theatre, you know I was intrigued. The buildup to its full release only increased its legend, as Pine himself, who admits to conceiving the film as something akin to a gag with Patty Jenkins on the set of Wonder Woman 1984 (itself a misfire that vies for this fabled fraternity of suck, so of course she gets a producer credit), seemed to lavish in the backlash, relishing the bad press as if it gave him strength. I had to see it. I had to know just how off it could be. The runaway worst film of the year so far was Madame Web, but could it be beaten? I needed to know.

Having finally witnessed this train wreck, I now understand why the crowds revolted, and why Pine has gotten off on the vitriol. This is not a Room-esque exercise in tonal or storytelling ignorance. It is a troll film. Not Troll 2, mind you, but a feature length practical joke. There are moments where you can’t help but laugh at the nonsense going on within its moving frames, occasionally showing that it could have been the delightful trash we use as a guilty pleasure, but they are fleeting. Instead, this vanity project has all the earmarks of an intentional taunt to those who handed over their hard-earned money, a 100-minute dare that’s so incompetently made that it makes you feel more sorry for Pine by the end than angry, because you know that in a weird way, it almost worked.

Playing out like a parody of Chinatown by way of The Big Lebowski (and you’ll notice this long before the several overt references to the former), Pine directs, co-writes, and stars as Darren Barrenman, the first in a long line of just plain lazy character names (the potential for a tongue twister never pays off), a scruffy washout pool cleaner at an old apartment building that looks more like a disused roadside motel. See, he works in the water, but his last name implies that he’s dry, GET IT?!?! His daily routine involves emerging from his converted camper home, putting on some classical music, getting into a zen-like state as he sits on the bottom of the pool, then skimming it before he goes back inside, has relations with his girlfriend Susan (Jennifer Jason Leigh having her most awkward on-screen sex since Fast Times at Ridgemont High), and writes a daily letter to — and I’m not kidding here — Erin fucking Brockovich, narrating his life and telling her about his advocacy work to make Los Angeles a better, more environmentally friendly city. He even keeps an empty frame on his wall reserved for her eventual response.

Within five minutes, you already know that this is madness. Pine’s character is uninteresting, his motivations are completely whack, and the derivative nature of his so-called “hero’s journey” is borderline obscene. And yet, this can all be entertaining as hell if he truly leans into the absurdity. However, there’s a difference between being over-the-top goofy and being half-assed, and this is squarely the latter.

Take the basic elements of production at play here. The cinematography is all over the place, with lighting that doesn’t highlight anything or feel natural. He picks a CD from a rack that appears to have several jewel cases from published works, only to pull one that is clearly a blank disc with a name written in marker. The editing and sound design have no logic to them whatsoever, as some underwater shots have drowned out noise while others are at full volume. Half the shots don’t even have basic foley sound effects. When he “writes” to Erin, it’s clear he’s writing to the character played by Julia Roberts (another reference made explicit later on in the film just to beat us over the head with his intent), rather than the real person. The fact that he hasn’t received a Cease and Desist letter for stalking beggars belief. And just for good measure, as he composes his musings on an old-fashioned typewriter, Pine just hunts and pecks randomly on the keyboard, his movements not in the least corresponding to his narration or what little text we show on the paper itself.

This screams that Pine either doesn’t know what he’s doing, or he does and he’s willfully doing it wrong just to try to be different without saying anything. This extends to the larger plot, where he works with the building’s owners, Jack and Diane (seriously?), played by Danny DeVito and Annette Bening presumably under threat of blackmail. They serve as parental figures to Darren, with Diane acting as a therapist (there’s a very odd scene where she looks directly at the camera while quoting something meant to sound profound but it just comes off creepy) and Jack trying to resurrect his career as a Hollywood producer by making a gonzo documentary with Darren about his attempts to beautify the community, sort of like Michael Moore if he had no resources, intellect, and had been recently bludgeoned by a cartoon mallet. There are multiple scenes where the three of them just talk and argue over each other, and each one is so loud — with no proper audio mixing — that nothing of substance can be understood from any of them. With their associate producer Wayne (John Ortiz) in tow, the group heads to a city council meeting — one that only has three people in it, in LOS ANGELES — where Darren petitions Councilman Stephen Toronkowski, played by Stephen Tobolowsky (I seem to remember a cartoon joke — I want to say South Park or The Simpsons — where Hector Elizondo stars on a TV show as “Hector Belizondo,” or something similar, and it feels like that was the extent of the creativity in the naming of characters) about an improvement to the city’s mass transit system before things quickly devolve into a shouting match without reason, and Darren is arrested.

Back at the apartment, Darren’s world is shaken by the arrival of June Del Ray — Jesus Christ — played by DeWanda Wise, a “femme fatale” trope so obvious and out of place that you’re too aghast to even bother wondering why Wise seemingly feels the need to wear a septum piercing in every movie she’s in, even when it’s not relevant to her character. She tells Darren that “Toronkowski” is corrupt, taking bribes from powerful businessmen (including Clancy Brown and Ray Wise; ignore all the obvious foreshadowing fairies when it comes to two actors having the same last name, because Pine is WAY too clever for that, wink wink) in order to steal the groundwater from underneath the town and turn it into a desert.

What follows from here is an absolute parade of ego, one where the complete lack of talent obscures the few instances of genuine intrigue and comedic potential. I mean, when I can’t even get into the madcap laughs that should be automatic about a cabaret-style stage performance of a Golden Girls episode because I’m too fixated on how an assassin can literally shoot someone without making their presence known in any way despite there only being one entry point that’s constantly in plain sight, what are we even doing here?

This is honestly the most infuriating part of the entire picture. If Chris Pine really wants to troll the audience, by all means go for it, but do it properly. Create something that’s at least technically proficient so that we can enjoy the ride. If we’re parodying film noir, there are myriad ways to go about it that are stylish, funny, and even occasionally insightful. Chinatown is one of the most brilliant entries in the genre, but it’s not without its flaws and foibles, and there are plenty of ripe opportunities to explore and exploit them, but you have to be at least functional in the presentation. I’ve seen first year student films made with more technical skill and personal passion. Here, it just feels like Pine’s dicking around and getting paid for it.

This is why it doesn’t rise to the level of The Room or Freddy Got Fingered. In the former, Tommy Wiseau had no idea what he was doing, and that pure amateurism wound up being part of its accidental charm. In the latter, Tom Green was at the height of his 15 minutes, and he knew the end of his wacky relevance was coming soon, so he took the money given to him and threw everything at the wall to make something as insane as possible. Chris Pine has no such excuse, on either end. He’s a well-established and highly accomplished actor with goodwill to spare. Even if he’s never directed before, he’s worked with enough stalwart professionals to know the basics. And given that he’s an A-list celebrity with traditional charisma and clout for days, he’s at no risk of having his star fall outside of a massive self-inflicted scandal, so he has no reason to go as bonkers as Green did, especially since this batshit craziness was always part of Green’s milieu. This is so far out of left field that it loops all the way back around to right field before beaning the audience in the head.

But at the same time, it’s also not as bad as Madame Web. That piece of shit was a crass, craven cash grab by a studio so desperate to hold onto a profitable IP that they’d churn out whatever garbage they can assemble in a week and then lie about it being great to dupe people into giving them money. There’s nothing redeemable about it on any level. Here, you can at least see where it could have worked, how fun it could have been, had Pine taken things seriously or put the matter in more capable hands. There are occasional flashes of substance here, to the point where I had a few honest laughs at how wrong it turned out, giving us that brief spark of unintentional genius that we crave in these types of movies. This is a film that you do kind of have to see to believe, which is probably the only part of the apparent goal that was accomplished. But at least wait until it comes on streaming. Let it develop a cult following if that’s what ends up happening. Do not reward this with your multiplex dollars, because that’s the only way the prank truly succeeds.

Because when it’s all said and done, this is a troll flick that doesn’t troll hard enough. It’s a poorly-made mishmash that was created by people who we all know can and do create better things, with no reason given for the incompetent display. It’s an attempt to be “so-bad-it’s-good” but because it’s so badly done the bad goodness just ends up being even worse badness. Chris Pine sticks rocks in his own pockets in an attempt to purposefully sink to the bottom of the great pool of art that is cinema. In the end, however, he ends up drowning in a puddle.

Grade: D-

Join the conversation in the comments below! What film should I review next? Have you ever seen someone TRY to win a Razzie? Seriously, what dirt does Pine have on his co-stars to make them do this? Let me know! And remember, you can follow me on Twitter (fuck “X”) and YouTube for even more content, and check out the entire BTRP Media Network at!

Originally published at on May 23, 2024.



William J Hammon

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