In Chris Pine's directorial debut Poolman, Pine himself stars as an amateur sleuth in Los Angeles who is dedicated to uncovering a mind-blowing mystery. The film itself is inherently a curiosity, as Pine has been about as enigmatic a figure as an A-list movie star can be nowadays. In the Best Chris Wars, he has thrived by playing quirky yet undeniably dashing heroes across films like Wonder Woman, A Wrinkle in Time, Star Trek, and Dungeons & Dragons: Honor Among Thieves. Yet unlike his peers in Chris-ness, he has not courted fandom through social media, and so has not been subject to political backlashes or parasocial relationship-spurred scandals. Instead, he has cultivated a mystique that involves preferring an old-school flip phone and busting out a disposable camera at movie premieres. Even the entrancing whirlpool that was the Don't Worry Darling promotional tour could not bring him down, despite being at the center of Spitgate.

Chris Pine has managed to float above so many Hollywood pitfalls with impeccable style. And yet Poolman is a comedy-noir that aims to lampoon the excesses and eccentricities of Hollywood (or, more broadly, Los Angeles) but fails to thrill or amuse — or give fans much of an insight into the mystery man behind it. Actually, the most profound mystery at the heart of Poolman is not its convoluted case of corruption, but rather why it doesn't work at all.

What is the buzz on Poolman?

Ahead of the Toronto International Film Festival, Poolman was a hotly anticipated title, not only because of its star-studded cast but also because the premise was drawing early comparisons to other L.A.-set comedy noirs, such as the Coen Brothers' The Big Lebowski, Paul Thomas Anderson's Inherent Vice, and David Robert Mitchell's Under The Silver Lake.

However, as audiences exited the first screening of the film (of which I was in attendance), there were whispers of confusion and frustration. The bad buzz only built as press screenings concluded. In a packed field of TIFF movies directed by actors, including Taika Waititi's Next Goal Wins, Michael Keaton's Knox Goes Away, and Anna Kendrick's Woman of the Hour, Pine's Poolman stood out as the most critically scorned.

What is Poolman about?

Chris Pine stars as Darren, a middle-aged pool cleaner who values meditation and activism, holding crusader Erin Brockovich as his personal hero. When he’s not writing her daily fan letters, he’s proving to be a thorn in the side of the local government, demanding improvements of bus routes through dramatic speeches, accompanied by personal anecdotes and poster board displays. But in a town where every nobody is striving to be somebody, even the pool guy is susceptible to the lure of fame.

When his quest to bring down a seemingly corrupt politician (Stephen Tobolowsky) leads to a run-in with the sultry June Del Rey (DeWanda Wise), Darren is quick to leap into the fray — stalking, scheming, going on stakeouts, doing origami, and bringing into his clumsy investigation a quirky circle of friends. Could this make him a hero to his hometown of Los Angeles? Or another fool forgotten in this treacherous city of dreams?

Annette Bening and Danny DeVito outshine Chris Pine in Poolman.

To his credit, Pine smartly casts his film with celebrated stars and stellar supporting players. Jennifer Jason Leigh brings a beguilingly blasé attitude as a Pilates instructor who is ostensibly Darren's girlfriend. DeWanda Wise, resplendent in fiercely fitted fashion with a Golden Age of Hollywood flare, sinks her dazzling teeth into her comically flirty and ferocious femme fatale. John Ortiz steals moments as Darren's ever-loyal yet endlessly bullied would-be bestie, and Stephen Tobolowsky gives a surprisingly tender turn.

Best of the bunch, though, are Annette Bening and Danny DeVito, a Jungian analyst and her blustering movie producer husband who make an unlikely but charming duo. Not only do they own the humble motel where Darren works, but this captivating odd couple is also his therapist and collaborator, respectively, and his parents, figuratively.

In scenes where the two coddle Darren amid his conspiratorial rants, there is something undeniably sweet and satisfying in Poolman. DeVito and Bening are an enticing comedic pair, in part because his chaotic energy clicks with her calm kookiness. Unfortunately, the characters themselves are woefully one-note, which turns the experience of enjoying their company into a stagnant overstay. Perhaps we can blame the script by Pine and Ian Gotler, which doesn't seem to know what else to do with these two beyond being capering sidekicks to the crusty but uncompelling hero. The other supporting characters are similarly promising but thinly realized.

While he's dazzled under the direction of many other helmers, Pine misjudges his own capabilities here. Even with a grizzle beard and ratty, long hair, he does not have the breezy coolness of Jeff Bridges as The Dude, or the frenetic magnetism of Joaquin Phoenix's Doc Sportello, or the chafing yet captivating cockiness of Andrew Garfield's Under the Silver Lake hero, Sam. Instead, Darren feels like a vague gesture at a harried but optimistic kind of Angeleno that may not read well to the wider world. Far from captivating, Darren is most often annoying. And his quest is often too confusing to invest in.

Poolman is a joke that never lands.

The cast is promising. The concept of an everyman taking on Goliath-level corruption is compelling. But as Pine's film references Hollywood-set noirs ranging from Chinatown to Who Framed Roger Rabbit?, audiences are forced to recognize how poor a comparison Poolman makes to its inspirations. One particular sequence in a dingy drag bar might urge audiences (especially if this movie lands on streaming) to click away and revisit those instead. Or, heck, even The Golden Girls — in that classic sitcom, the plots made sense, and the punchlines hit hard and often!

Part of the problem is that Pine's narrative is confounding, not just to his confused hero but to any audience member who dares to follow him. There are occasionally exposition dumps, as well as insert shots to be sure the audience caught a pivotal (and obvious) plot twist. But none of this is put together in a way that allows us to follow Darren's logic or his righteous outrage. As Poolman lumbers into its cacophonic climax, audiences might relish in some silliness, but they likely won't feel sated by the mystery's solution.

That the plot barely makes sense might’ve been forgivable if Pine could elicit from his performers the kind of exhilarating energy and distinctive wackiness we’ve seen in the works of the Coens and Anderson. Instead, his cast, while charismatic, dances between a blurry line of broad comedy and nuanced parody that can't find its footing. Theirs is a world vaguely interesting but never sharply realized. And as such, we, the audience are always treated as outsiders.

In the end, Poolman plays an inside joke that never let its audience inside.

Poolman was reviewed out of its world premiere at 2023's Toronto International Film Festival.