Tomorrow, I get to travel to Portland — a city I’ve never been to, strangely enough — for fewer than 24 hours for work. Getting ready for this trip got me thinking about Gus Van Sant, who has set so many of his movies in his adopted hometown in the Pacific Northwest.

So I went back and looked up a Five Most list I put together of Van Sant’s best films back in September 2011. As you’ll see, I fudged it a little and added a sixth title. Enjoy.

5 best Gus Van Sant films

By CHRISTY LEMIRE

LOS ANGELES  — Gus Van Sant has made an eclectic array of films over the past quarter-century, but throughout that time he’s repeatedly explored the restlessness of youth.

This week, the director is out with his latest — which happens to be titled “Restless” — about a couple of teenagers (Henry Hopper and Mia Wasikowska) who are fascinated with death. It’s not a career highlight for him — it never achieves the emotional resonance it seeks — but it provides us with a good opportunity to pick five of his best films. A quick note: I would have loved to have found room for “Paranoid Park,” but I only get to pick five. That’s why the game is fun:

_ “Good Will Hunting” (1997): Van Sant sometimes makes small, quiet films that challenge your attention span, and I admire him for such daring. But one of his most mainstream movies also happens to be one of his best. Nominated for nine Oscars (including best picture), it won two: for supporting-actor Robin Williams and for the original screenplay from co-stars Matt Damon and Ben Affleck. Its uplifting story arc may be formulaic but the strength and honesty of the performances give it surprising emotional heft — especially from Damon as a troubled math genius in the role that marked his arrival as a major, serious actor. And the sense of place Van Sant evokes of working-class Boston is inescapable.

_ “Milk” (2008): On its surface, this could have been shamelessly mawkish. Instead, Van Sant presents the last eight years in the life of Harvey Milk, the slain San Francisco politician and gay rights activist, with a mix of vivid details and nuanced heart. He’s also drawn from Sean Penn one of the most glorious performances ever in the actor’s long and varied career, one that duly earned Penn his second best-actor Oscar. “Milk” also won an Academy Award for Dustin Lance Black’s original screenplay. It hits all the important marks but never feels like a typical biopic, a superficial, greatest-hits collection. Jumping back and forth in time, “Milk” flows easily and comfortably; it makes us feel like we’re witnessing the natural, propulsive drive of a life that mattered.

_ “Drugstore Cowboy” (1989): An all-time classic drug movie, it realistically depicts the desperation that takes hold when you’re hooked. It’s also a great movie about criminals on the run, and how they create their own little universe while trying to avoid the real world. Matt Dillon alternates between cool charisma and manic superstition as the leader of a group of junkies (Kelly Lynch, James Le Gros, Heather Graham) who rob pharmacies to feed their habit in 1971 Portland. In their own screwed-up way, they’re formed a community, and they look out for each other. Their lives are cheaply thrilling and deeply sad.

_ “To Die For” (1995): A pitch-black, razor-sharp satire about the desire for fame and the lengths to which people will go to acquire it. Nicole Kidman is both hilarious and frightening as a perky but driven small-town wife with dreams of becoming a big-name television personality. In an array of candy-colored get-ups and a perfect coif, she’s a Barbie doll with ice water in her veins. But her dark side reveals itself as she plots to kill her husband (Dillon, again) with the help of some misfit teenagers (including Joaquin Phoenix and Casey Affleck). Working from a script from Buck Henry, himself a TV veteran, Van Sant never lets up on her, or on the characters who might have seemed innocent at the film’s start.

_ “My Own Private Idaho” (1991): It’s impossible to look back on one of River Phoenix’s films without feeling great sadness and wondering what might have been. Here, he plays a scruffy, narcoleptic hustler named Mike who’s woefully adrift and in need of some human tenderness. It’s a delicate performance in a dangerous world and watching it, you long to see him protected and safe. His only real friend is Scott, played with cool confidence by Keanu Reeves. He hustles not because he needs to — the son of Portland’s mayor, he has a large inheritance coming his way — but because it’s rebellious. Together they navigate a landscape that’s both absurd and dreamlike.