DirectorGus Van Santisthe brains behind gemslikeDrugstore Cowboy,Good Will Hunting, andMilk.
Van Sant is a filmmaker equally comfortable with unstructured character studies and award-season prestige.
His best work captures a sort of haunted beautya quiet fascination with lost souls, wanderers, and misfits.

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With this in mind, this list ranks Van Sant’s must-see movies, fromMala NochetoFinding Forrester.
It’s a bad night."
This is a film that’s less about plot and more about longing.

Walt’s inner monologue provides much of the films reflection, laying his inner tension.
Overall, the movie feels personal and unique, the work of a singular voice.
Not bad for a first-time director.

This approach occasionally comes across as too artsy or overwrought but, in general, it works.
To get there, shes willing to manipulate, seduce, and even murder.
It makes for a barbed statement on muckraking media and true-crime stories.

This critique was arguably ahead of its time, and the dynamics it skewers have only become more ubiquitous.
So why shouldnt I do stand-up?"
Joaquin Phoenix leads this film (based on a memoir) as quadriplegic cartoonistJohn Callahan.

He’s a recovering alcoholic who finds purpose and fame through his brutally honest, often offensive cartoons.
Nevertheless,it compensates with a funny, messy, life-affirming script and winning performancesfrom the leads.
Phoenix is defiant and magnetic, while Hill is refreshingly restrained, almost becoming the movie’s emotional anchor.

The pair undertake a slightly surreal journey from Seattle to Idaho to Italy.
There are animated sequences and whiplash tonal shifts.
But there’s authenticity and vulnerability alongside the artifice, particularly from River Phoenix.

This was one of his defining performances: tender, haunted, and loaded with gravitas.
But theres no traditional narrative hereno explanations, no backstories, no closure.
The effect is chilling and disorienting.

The largely unknown cast improvised within Van Sants loosely structured framework, adding to the documentary-like feel.
Butit does so with surprising grace and restraint, elevated by strong lead performances.
They’re not depicted as bad people but rather as damaged people under a lot of pressure.

With Van Sant at the helm,Milk becomes a deeply personal yet urgent portrayalof Milks life.
Some moments are a little corny (like the “How you like them apples?”
Damon, young and raw, matches him beat for beat.

The dynamic between them is touching and hard-earned.
NEXT:The 10 Worst Movies That Tried To Be Social Commentary, Ranked




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