In a few years, Noah Baumbach’s Greenberg will likely be regarded as one of the quintessential indie films of its time. It isn’t a startling or groundbreaking work, but it’s a very good addition to an upper-middle-class genre. Aside from being an observant and offbeat character study, and impeccably cast—from a random hook-up on down—it may also be the subtlest, funniest, and best-written rumination on the gap between Generation X and my fellow millenials—the worst-named cohort since the baby boom. It’s Gen X idealism coming home to roost.

As Roger Greenberg, 41, Ben Stiller pulls off the most challenging role I’ve seen him play. His mock snarl is as effective for Roger as it was for Derek Zoolander, but this time he doesn’t warp his malleable facial muscles into simian contortions; his key features here are those beady eyes. There’s always been a constancy behind them—a stillness that helped form Stiller’s deadpan—but now they’re used on behalf of Roger’s myopia. This guy is so easily peeved that he redresses every bother with a hand-written diatribe; most of them are probably greeted by snickers and then tossed into the trash—but that doubtfully crosses his mind. He’s a native Los Angeleno who escaped to New York, but has now—temporarily—returned to California, by way of a mental hospital. He’s the caretaker of his brother’s mansion; Phillip’s whereabouts and with-whom-abouts—a business venture in Vietnam with his lovely wife and children—are measures of his success. Roger almost signed a record deal for his band right after he graduated from college; but he was too stubborn to accept the terms, and he and his bandmate, the pilose recovering addict Ivan (Rhys Ifans), have been in a holding pattern since.

Although he’s building a dog house for Phillip’s German shepherd, Roger is ardently committed to doing nothing. Nothing includes trying to rekindle his relationship with Beth (Jennifer Jason Lee, who came up with the story with real-life hubby Baumbach, and wears blocky hipster glasses here), who’s now married/with children. He also catches up with another former bandmate, Eric (Mark Duplass), who chides him for ruining his and Ivan’s lives—although, unlike Ivan and Roger, Eric’s struck it rich. But, most importantly, Roger gets frisky with Phillip’s diffident 25-year-old assistant, Florence (Greta Gerwig). She likes Roger because he’s vulnerable—like her. But he’s also sensitive in the wrong way; he has a hairpin trigger. (When Ivan has the waiters sing happy birthday to him at Musso and Frank’s, Roger stands up and yells, “Go sit on my dick!”) Florence can’t have a real relationship with Roger because he keeps telling her she shouldn’t.

It’s tempting to say that Roger, who’d consider a glass to be 50.33367% empty, is a Woody Allen figure—and by casting Chris Messina (Phillip) in the same yuppie role Allen palmed off on him in Vicky Cristina Barcelona, it’s almost as if Baumbach were tipping his hat at the elder director. (Either that or Messina’s naturally suited to play suits.) But Baumbach is less openly reproachful of his nebbishes; he’s less likely than golden-age Allen—whose subject was usually his love-hate relationship with himself—to make any judgments. As much as I love Wes Anderson’s frilly Rushmore, Baumbach has a firmer mastery of the exacting but sympathetic tone of J.D. Salinger stories. Roger bridges the gulf between troubled-teen-son Jesse Eisenberg and complacent-intellectual-father Jeff Daniels from The Squid and the Whale, and Stiller is playing an equally Salingerian hero: Roger probably didn’t act young when he was younger, and he’s still too immature to pass as old. When he’s surrounded by 20-year-olds at his niece’s house-party, he doesn’t seem out of place—that is, he seems in the habit of seeming out of place. (There’s always that clueless oldster at parties like that, you know? And this shindig is, by the way, the most authentic of its type that I’ve seen thrown in recent movies. There’s even a cokehead wearing my cardigan!) As Roger’s redeemer, Gerwig plays her part beautifully—even if Florence is something of an indie-movie trope: She’s Wendy to wannabe Peter Pans like Roger. We never see her take a toke, but she always seems a bit high. Maybe it’s part of the generational critique. Anchorless, Flo floats; rudderless Roger is a sinker.

Greenberg is like a mature Garden State in the Golden State; it isn’t as artsy-fartsy-cutesy. (Baumbach may be a frequent collaborator with Anderson, but the former’s style is more grounded than the latter’s air quotes.) This film also saunters over Gen X touchstones like Richard Linklater’s early work or Reality Bites, a post-grunge, pre-Youtube proto-Juno (though not so methodically phony) that Stiller directed in 1994. He also played a yuppie, and tried to prove that you can join the Establishment and still be a nice guy—a strain that runs through Stiller’s performances (including the movie star he played in the always-verging-on-hilarious Tropic Thunder), and which helps to keep the inward, griping, narcissistic Roger from being just an inward, griping narcissist. But his yuppie didn’t get the girl. That distinction went to slacker-rocker-philosopher Ethan Hawke—who, on the basis of Greenberg, probably ended up getting dumped and turning into an in-patient wackadoodle like Roger.

(Roger, actually, never really “gets” his girl, either. One can see the shift between the true-love-forever mentality in Reality Bites and the it’s-complicated culture that Greenberg is enmeshed in. Comedies used to conclude with weddings; nowadays, in this urbane sphere, lovers can’t even commit to being in a relationship on Facebook. This cyber stratum is beyond Roger’s ken. Maybe it’s not a novel point, but Baumbach’s focus on an incorruptibly flaky “little guy” who, creeping past 40, still can’t meet life’s minimal requirements for selling out, is part of what makes this movie such a timely indie. The modern indie-realist hero isn’t on the margins of society; he’s on the outskirts of the middle-class viewer’s social clique—the wince-worthy fellow on your caller I.D. Roger Greenbergs are a lot easier to feel for and grapple with when they’re not mucking up your off-screen life.)

Now this is where the roosting comes home to … roost. The Xers grew up in the ’80s; they didn’t want to be sellouts like the hippies, but were too enervated to rebel like in the ’60s. This dialectic has left Roger batty. I’m speaking in very general terms, of course; to Greenberg’s credit, our hero is a character and not a stand-in for the 46 million people born between 1965 and 1980. But it’s interesting to see the Xers at the cinematic crossroads the boomers were at circa The Big Chill (1983). Boomer-baiting movies have sort-of bypassed their initial how-did-we-become-the-people-we-reviled self-critique, leaving us with sentimental—*cough*, in denial—fluff like Pirate Radio. (Maybe the regrets submerged in Hot Tub Time Machine are a form of denial, too.) In this fractured, D.I.Y. media culture, Garden State and Superbad may be the closest we millenials get to an Easy Rider or a Breakfast Club or a Rebel Without a Cause. If the Man gets us down, we blog about it. (Guilty as charged.) Still, I’m curious to see how Xers will be depicted by the time we shiver from our big chill. Let’s try to stay warm.