In the 1990s the Hollywood studios made tentatives steps towards making the ultimate “Generation X” film; something that could capture the zeitgeist of disaffected Americans in the 20s in a way that John Hughes’ popular teen dramas had captured their adolescence. Richard Linklater’s Slackers (1991) was a key early attempt, but it was an independent film, and not shepherded by any studio to profit from the Gen-X market. Cameron Crowe’s much-hyped 1992 effort Singles was one notable contender, basing itself within Seattle’s grunge scene and making Warner Bros a modest profit. Another major attempt was Ben Stiller’s 1994 comedy-drama Reality Bites, which tracked four university graduates in the year after finishing college. It was a bigger hit than Singles, and remains something of a cult favourite to this day.

Lelaina Pierce (Winona Ryder) is valedictorian of her graduating class, and aspires to become a documentary filmmaker. When she meets young TV executive Michael Grates (Stiller) she falls into a love triangle between him and unemployed slacker Troy Dyer (Ethan Hawke). Meanwhile her housemates face challenges of their own: Vickie Miner (Janeane Garofalo) awaits the results of a HIV test, while the closeted Sammy Gray (Steve Zahn) prepares to come out to his unsuspecting mother.

The film is now more than 25 years old, so revealing critical plot details seems forgivable in this case – if you have never seen Reality Bites and want to, skip to the end paragraph now.

Reality Bites eerily reflects its own making. Just as Lelaina trusts her incomplete documentary about her friends with Michael – only to see it brutally transformed to fit a commercial pattern – so too real-life Helen Childress went through an alleged 70 different drafts of her semi-autobiographical screenplay before it was suitably tailored for mass consumption. The four key housemates were originally based on real people. Michael, whose actions lead to the unwanted commodification of Lelaina’s work, is a fictional character invented to commodify Childress’ story and make it more palatable to a mass audience. I cannot work out if this is the greatest of all coincidences or a spectacular example of a writer biting the hand that’s paying their rent.

Michael is a fascinating character to watch, and Stiller’s performance in the role is grossly underrated. He is rich, slick, willingly corporate, and seems artificially designed to give Lelaina a romantic choice and make her acceptance of Troy a more natural choice to make by the climax. At the same time Stiller – as both actor and director – cannot help but make him a personable and likeable character. They meet because Lelaina throws a cigarette butt out of her car window and it causes his car to crash into hers. He forgives this, and does not even ask her for money to pay for the damage. He shows an interest in her art and her work, going so far as to try getting his superiors in youth television interested in her documentary. When that backfires spectacularly, he goes out of his way to apologise and make amends. He pursues her respectively, and once she rejects him he exits the picture entirely. In the grunge-tinted, slacker world of mid-1990s cinema, however, he is a poor match. He wears an expensive suit, and “works for the man”. Lelaina’s rejection of him in favour of Troy is a foregone conclusion.

That is, it must be said, a terrible conclusion. Troy spends the bulk of the film mocking and insulting Lelaina, like a small child forgiven for pulling a girls hair because “that just means he secretly loves you”. His abusive behaviour occupies a vague sort of rebel aesthetic – the failure to hold down minimum wage jobs, and the constant insistence he is going to form a successful rock band – but 2021 is not 1994, and particularly in this future time Troy’s behaviour reflects particularly badly on him and the film.

Watching Lelaina choose him is a natural conclusion then, but a heartbreaking tragedy now. It is going to be a terrible relationship, and in retrospect you can see its inevitable collapse from orbit. Viewed from the appropriate age, however, and it is every sort of romance that twentysomethings of the mid-1990s thought was desirable. Reality Bites may no longer operate particularly well as romantic comedy-drama, but it excels as a time capsule of American culture.

The “time capsule” nature of the film extends to its soundtrack, packed not just with contemporary hits of the time but also older music that resonates with Generation X nostalgia. The Knack’s 1979 hit “My Sharona” is a key example, used so iconically that decades late the song and the film feel permanently sealed together. Also strong are the subplots for Garofalo and Zahn; they’re both fine actors making breakout performances here, and their own personal crises provide a valuable diversion to the weirdly artificial love triangle. It also feels a significant role for Ryder, marking her first popular conventional role since breaking out herself in 1988’s Beetlejuice. Having forged her reputation on period films and cult and arthouse fare, Reality Bites probably marked the first successful mainstream role she had played.

It is a confident directorial debut for Ben Stiller, and he gives the entire picture a quiet sense of cynicism about the edges. A mid-credits sequence, depicting the youth network’s rip-off remake of Lelaina’s documentary, pokes at exactly the right corporate forces that backed the actual movie. Stiller remains an underrated director, with a specific gift for this kind of self-aware sharpness. His movies are often commercially successful – including The Cable Guy, Zoolander, and Tropic Thunder – but he rarely gets the critical plaudits that he deserves.

Reality Bites is of its time, and as that time passes further and further away it is beginning to lose much its original energy and relevance. As a depiction of a particular age in a particular country for a specific generation, it is still a pleasant nostalgic trip.