You would think that the master chronicler of the travails of Generation X — my generation, those of us who were born between 1965 and 1980 and came of age in the 1990s — must be either Richard Linklater or Cameron Crowe. And you wouldn’t be wrong, given the strong films they’ve made over the years reflecting the highs and lows of this generation: Slackers and Singles are sacred titles in the pop cultural altar of Generation X.
But as far as I am concerned, Ben Stiller takes the crown, or at least occupies an honored place in a triumvirate, not just as director but also as actor. Stiller, who is known primarily as a comedy actor of a very specific type, that of an intense and put-upon bloke always on the cusp of exploding, is an impressive director. But this specific career trajectory in his life is less heralded — although once you do the quick survey, his filmography is actually considerable.
Reality Bites  — where he made his feature directing debut and which starred Winona Ryder, Ethan Hawke, Stiller himself, Janeane Garofalo, and Steve Zahn in their prime — is very much his ticket to the Gen X pantheon.
In this movie, he distilled with surprising thoroughness that generation’s  aesthetics [slacker clothes, Gap, and MTV-style edits],  life soundtrack [from The Knack’s “My Sharona” to Lisa Loeb & Nine Stories’ “Stay (I Missed You)”],  preoccupations [participating in a navel-gazing documentary, where each one would bear their respective demons — i.e., dealing with high expectations when you’re feeling lost in a dead-end job, coming out gay to one’s parents, dancing with self-sabotage by slacking away the world, and dealing with sexual addiction and its attendant fear of contracting HIV], and  their language of ennui and disenchantment.
Take Ryder’s Lelaina Pierce and her valedictory address in the college graduation that starts the movie. Looking at her index cards, she punches out her words with powerful condemnation of the Boomer generation that came before her: “And they wonder why those of us in our twenties refuse to work an 80-hour week just so we can afford to buy their BMWs, why we aren’t interested in the counterculture that they invented, as if we did not see them disembowel their revolution for a pair of running shoes. But the question remains, what are we going to do now? How can we repair all the damage we inherited? Fellow graduates, the answer is simple. The answer is…”
She fumbles for the next card, but it is missing.
“The answer is…,” she continues, faltering, and then realizing she has to wing it, ends with this existential conclusion: “I don’t know.”
I don’t know.
That’s the film baring its thesis — and its diagnosis of the Gen X spirit — right from the get-go. As a young adult in my early 20s in 1994, dealing with my own existential dilemmas, that line made me feel seen. And as the movie unfolds, their gang of four, finding themselves living together in the same apartment, must navigate the real world’s blows to their youthful promises and egos, must learn to negotiate the fine line between ambition and selling out, and must deal with the non-theoretical repercussions of their decisions, their shortcomings, and their needs to be loved.
In Lelaina, Troy, Vickie, and Sammy, many of us in my generation found avatars for all our complex facets: young people just winging it, because we “don’t know.” But, today, it is funny to consider that of all the characters in the movie, it is actually Ben Stiller’s Michael that seems to have everything figured out — he has a very good job in a creative business, he makes great financial decisions, and he is actually nice.
But it is actually telling that the movie would cast him as the pseudo-villain in the grand scheme of things: that what he represents is unoriginality and compromise. He “knows,” and thus cannot be trusted. Troy, on the other hand, is beautiful and smart, but he is an irresponsible slacker, and terrible in his treatment of Lelaina — but the movie casts him as the romantic hero, his sexiness marked by his unshampooed mop of hair, his dreamy eyes, and his hyperarticulation that bends trivia as a weapon against unsuspecting buffoons. He embodies “I don’t know” in its raunchiest and most rebellious, and thus is not suspect.
But this is all in hindsight, of course.
When I first saw the film, Ethan Hawke felt like my hero, and undeniably he stirred carnal thoughts in young Ian, and I would go on to devour his direction of the music video for “Stay” [groundbreaking!] and his novel The Hottest State [heartbreaking!]. I was in love, a crush that started with Hawke’s dreamy defiance in Dead Poets Society . He would become 1990s cinema’s poster boy or heartthrob of ennui, following up this 1994 film with a series of roles that consolidated his stature: Jesse in Before Sunrise , Jerome in Gattaca , Finn in Great Expectations , Ishmael in Snow Falling on Cedars , the Prince of Denmark in Hamlet , and Jesse [again] in Waking Life . (They’re all variations of Troy, if you think about it.) But his adult, Oscar-nominated turn in Training Day , where he plays a rookie cop initiated into corruption, would punctuate that run, and end his reign as dreamy slacker prince.
In the meantime, this 1994 movie, which was not a box office hit when it premiered [it landed fifth in its opening weekend], has only grown in stature, become a cult hit, and end up as a calling card for one generation. It would teach us quips such as, “A master at the art of time suckage,” or “A non-practicing virgin,” or “There’s no secret handshake. There’s an IQ prerequisite. But there’s no secret handshake,” or “I am not required to make the world a better place,” or “You have reached the winter of our discontent,” or “He’s the reason Cliffs Notes were invented,” or “My goal is … I’d like a career or something,” or this gem: “Evian is naive spelled backwards.”
Stiller would go on to make other films — The Cable Guy , the Zoolander movies [2001 and 2016], and Tropic Thunder  — but for me, 2013’s The Secret Life of Walter Mitty would prove equal to the generational examination and reckoning he first ventured into in his 1994 directing debut.
In Walter Mitty, the Gen X persona has become middle-aged and burnt out, dreaming of escape from the choices he has made. In his youth, he rallied against the consumerism and compromise of the Boom Generation, but here is, finding out we are all the same under our skin, reality biting forever. But at least in the movie he finds escape, and redemption — because The Secret Life of Walter Mitty is our final fantasy and antidote to “I don’t know.”
No such antidotes exist for a slew of Ben Stiller Gen X characters in movies directed by others, especially those dealing with middle age: Noah Baumbach’s Greenberg  and While We’re Young , and Mike White’s Brad’s Status  — his persona still lost in the sea of “I don’t know,” but finding grace that perhaps it’s fine to flail, as long as you strive to be a better human being against all the existential odds.