It seems impossible to write the name “Ethan Hawke” without putting the words “generational icon” somewhere nearby. I don’t know how Hawke feels about this, but it used to bug me. Now, I welcome it. I look at Hawke differently now than I did when he first became shorthand for all things Generation X, my generation, a generation whose temperament made us reflexively reject attempts to define us. But it’s largely because Hawke’s choices suggest that he takes his icon duties seriously by appearing in role after role—up to and including his part in the new film Juliet, Naked—that doubles as commentary on how Gen X has progressed through the years, the prices we’ve paid in the process of growing up, the mistakes we’ve made, and our fears for a future that only yesterday seemed like ours to reshape and now feels out of our control. And it all started with a movie that tried just a little too hard to capture the spirit of a generation, one that gave Hawke a character with every slacker stereotype hanging off of it.

“It was strange afterwards,” Hawke recently told The Guardian of his experience making the 1994 film Reality Bites. “I was constantly meeting people who thought I was full of myself. They thought I was Troy – and they really didn’t like him.” Dummies, right? Except I was one of them. It took me a while to stop seeing Hawke’s performances, and maybe even Hawke himself, as an extension of Troy Dyer, one-third of the love triangle at the center of the Helen Childress–scripted, Ben Stiller–directed film in which Winona Ryder plays a recent college grad named Lelaina who’s trying to start a career as a documentary filmmaker. Stiller costars as Troy’s competition, a slick, well-dressed, success-bound executive at an MTV-like network who takes both a romantic and professional interest in Lelaina.

As played by Hawke, Troy is the embodiment of every “Who is Generation X?” article that made the rounds in the brief window when the media tried to figure out what to make of the generation born in the years after the Beatles played Sullivan but before Olivia Newton-John had a no. 1 hit with “Physical.” He defaults to irony, peppers his sentences with references to old movies and commercial slogans, and has no use for authority or attachment. He scowls. He broods. Above all, he slacks, crashing on Lelaina’s couch after losing his job for getting caught stealing a candy bar. He wears his intellect like a coat of armor, reading Being and Time in a diner while ignoring everyone else around him.

He kind of sucks, I thought at the time, but I feel a lot more charitable now, to Troy, to the movie, and especially to Hawke. Reality Bites arrived in theaters enveloped in “film of a generation” hype, hype the film itself sometimes seems to buy into. Flannel gets worn. Old sitcoms get referenced, repeatedly. Janeane Garofalo’s character carries a Charlie’s Angels lunchbox, works at the Gap, and spends much of the film worrying about the results of an HIV test. Toward the end, Lelaina watches in horror as her earnest, what-does-it-all-mean documentary becomes fodder for a Real World–style program that grossly simplifies the lives she’s attempting to document. The worst thing you can say about Reality Bites is that it accidentally does the same thing, and that even an actor as talented as Hawke could only halfway succeed in making Troy more than a generational stereotype.

But here’s the thing about generational stereotypes: Some of them are true, or at least closer to the truth than we want to admit. Maybe it’s the fogginess of nostalgia, but looking at Reality Bites now I’m more struck by what it gets right about being 20-something in 1994 than what it gets wrong. I can also now see that I disliked Troy in part because he reminded me of my own worst, stereotypically Gen X tendencies. I never shared the traits that made Troy attractive to others (to say nothing of Hawke’s disarming good looks), but the unearned sense of superiority and intellectual disdain are parts of my younger self that I’ve tried to burn off over the years. And anyone who backpacked around Europe with multiple books by Jean-Paul Sartre around the time of Reality Bites’ release can’t really scoff at Troy reading Heidegger at a greasy spoon.

Reality Bites tied Hawke to Gen X so tightly that he could easily have cornered the market on playing Troy-like characters for as long as the movies needed good-looking slacker types (so, until roughly late 1998). Part of what’s made his career so compelling isn’t just that he avoided that trap but found roles that played off that type. It helps that he quickly followed Troy with the part of a lifetime, almost literally. In 1995, Before Sunrise was released. It’s the first of Hawke’s many collaborations with writer-director Richard Linklater, and the first to feature the character of Jesse Wallace, which he’d reprise in two sequels to date and a brief appearance in Linklater’s dream movie Waking Life.

First seen drifting toward Vienna for his last night of a European trip filled with heartbreak and sightseeing, Jesse comes off as a more open, empathetic variation of Troy. It’s easy to believe he can charm Julie Delpy’s Celine into disembarking the train and wandering around Vienna with him, and that he can get out of his own head enough to appreciate the experience. Over the course of a single day, they flirt and fall for each other while trading thoughts on their lives, their disappointments, their hopes and fears for the future, and everything else swirling around the heads of two people in their early 20s who’ve unexpectedly found someone else who really gets them.

Before Sunrise ends with Jesse and Celine promising to meet again six months later, rolling the credits before we find out if either showed. And, for years, it looked like we’d never know. Then came Before Sunset in 2004 with an answer to that question and a new, digressive, meaningful Jesse-and-Celine conversation that finds them at much different stages in life, as they talk about politics and marriage and the way doors start to close as your 20s turn into your 30s. Before Midnight arrived nine years after that. Jesse and Celine have paired off at last, but they’re now having conversations defined as much by the topics they avoid as the ones they discuss.

One of the wonders of what Hawke and Delpy do in these films—they’re credited as cowriters with Linklater from the second installment on—is how they portray Jesse and Celine as changed by time while remaining recognizable as the kids we met in 1995. Now they’ve been battered about by life. They’ve experienced losses they never expected and made choices they sometimes have a hard time justifying to themselves. The breathtaking ending of Before Sunset finds Jesse making a romantic decision to stay with Celine in Paris, but there’s a betrayal of his family back home folded into that moment. Before Midnight doesn’t shy away from depicting its consequences, not just for Jesse but for others in his orbit.

The changes Jesse goes through in the Before films aren’t specific to Gen X, but having Hawke in the role makes the association unavoidable. Here’s where being a generational icon can enhance a performance rather than weigh it down. Disappointment, free-floating disenchantment, marital woes, unexpected passions, political disillusionment, and newfound fears come to every generation, but do they ever not come as a shock? I’m almost exactly the age of Hawke’s Before character, and with each new installment I’ve heard concerns I once never thought would come into my own life—some I’ve experienced firsthand, some I’ve seen my friends go through, some I’ve seen as paths not taken—echoed on screen. Each installment feels like checking in with an old acquaintance, but also a whole generation. How are we doing? What’s worrying us now? Are we going to make it?

It’s rare that an actor gets an opportunity to play out a character’s progress over so many years, much less twice, thanks to Linklater giving Hawke a chance to do something similar in compressed form in Boyhood. Hawke makes use of the opportunity beautifully. (As does Delpy, but that’s the subject of another piece.) We watch as a character synonymous with being young and eager to explore the world in a particular time and place has to deal with the passing of time and the world changing in ways he couldn’t have predicted. He grows up and gets old, an icon who doubles as a mirror.

By the early 2000s, I’d come to look forward to Hawke’s performances, thanks to his work in films like Hamlet and Training Day, even if it wasn’t until later that I realized he’d unexpectedly become one of my favorite actors. His work since then hasn’t changed that opinion, both thanks to his performances and the way he’s navigated his career, alternating between roles in which he can be searingly great (Before the Devil Knows You’re Dead, the underseen Born to Be Blue) and a burgeoning directorial career (including the terrific documentary Seymour: An Introduction and the forthcoming Blaze) and appearances in ambitious genre movies like Predestination and The Purge. Even here that generational icon status helps. In The Purge, Hawke plays a security expert who’s gotten rich off the policies of a government that’s legalized murder, and to see a representative of a generation that promised never to sell out becoming the ultimate sellout brings an added shock.

We may never see Jesse Wallace again, but 2018 has seen Hawke twice playing roles that draw on his iconic status. Adapted from Nick Hornby’s 2009 novel of the same name, Juliet, Naked stars Rose Byrne as Annie, a museum curator in a coastal English town whose boyfriend, Duncan (Chris O’Dowd), a university professor specializing in pop culture, idolizes Tucker Crowe (Hawke), an early-’90s rock star who more or less disappeared after one album, leaving behind 20 years of rumors.

In one of Juliet, Naked’s funniest moments, the Jesse Peretz–directed film puts the rumors to rest, introducing Crowe with a smash cut to a bedraggled Hawke walking through a big-box store mid–shopping trip. What’s happened to Tucker Crowe is, well, basically nothing. He’s bounced from relationship to relationship, fathered some kids, and now leads a pretty meaningless existence living off royalty checks in the guest home of an ex. Hawke plays him as a man who’s mostly let life slip away, turning him into a worn-out, full-bellied version of the rock star he once was, a man whose charm has started to erode and whose bad habits have started to catch up with him. He could be Troy Dyer if Hey, That’s My Bike had gotten signed to a major label and allowed him to indulge his worse impulses for a few years.

Neither the film nor Hawke let Tucker be a punch line, however. Hawke brings a soulfulness to the performance, treating Crowe as a man trying to find his way back after too much time in the wilderness, wondering if he can make amends for past mistakes and staring down mortality for the first time, thanks to a heart attack. Another actor might have worked in the part but, once again, Hawke’s history brings an added element. He’s a generational icon playing a generational icon reaching the point in life when the choices of his youth have started to have personal and biological consequences, a time when midlife crises and health problems stop being issues for some theoretical future but the realities of the here and now.

That sense of a whole generation’s bill coming due also pervades Hawke’s work in Paul Schrader’s First Reformed, one of the year’s best films. Hawke plays Ernst Toller, the pastor of a church kept open mostly for its value as a historical tourist attraction. His attempts to counsel Michael (Philip Ettinger), an environmental activist who’s fallen into despair, accelerate a preexisting crisis of faith and heighten his awareness of the possibly irreparable harm we’ve done to the earth, the role corporations have played in this, and the ways his own faith and the corporate-backed megachurch to which his own reputation is attached have abetted the damage.

Even here, the film that bound Hawke to Generation X has echoes. “How can we,” Ryder’s Lelaina asks in the valedictorian speech that opens Reality Bites, “repair all the damage we inherited?” Her character doesn’t have an answer. Neither does Hawke’s. But, at the time, we at least thought we might find it. We read 50 Simple Things You Can Do to Save the Earth. We knew we wouldn’t buy into the corrupt system handed to us by previous generations. We didn’t know how, but of course we were going to fix it. Yet, here we are, with problems that remain not just unfixed but worsening.

Part of the power of First Reformed comes from its depiction of Ernst’s deepening despair as possibly justified. He may just be clear-headed about the long path down ahead of our generation and all those that follow. But it’s also a film that finds value in grasping for hope and grace even in the face of some dark fate, of looking for answers even when there may not be any. Ernst is a link in a long chain of Hawke characters who double as depictions of a generation’s progress, know-it-alls who have evolved into men who know they don’t know, but also know that they have to keep searching. That’s why we keep looking to him.

Keith Phipps is a writer and editor specializing in film and TV. Formerly: Uproxx, The Dissolve, and The A.V. Club.