Why do nice guys finish last?

The question contained in the title is a recurring theme in the films of Whit Stillman, which are largely autobiographical. With the release of Damsels in Distress (covered in these articles by The Atlantic, Wall Street Journal and The New Yorker) late last year after a thirteen year hiatus, it seemed befitting to relive some of the most memorable moments from his previous work. Even the initial sampler to Damsels, which can be viewed here, demonstrates the actual "problem" of female attraction to the dark male character. By reviewing what went before, we can probably shed some light on the topic at hand.

In this first clip taken from the Oscar-nominated Metropolitan (1990), we can get a flavor for Stillman's comedy of manners. As Nick Pinkerton in The Village Voice put it,  the film presents us with

the milieu of its writer-director—Preppie, Yuppie, Urban Haute Bourgeoisie—and treated it, not as something to be pilloried or taken for granted, but as a suitable subject for his characters' study, even defense ... It applied the emotional delicacy of the 19th-century courtship novel to the sexual revolution's aftermath—for Stillman, something more ambiguous and disorienting than the accepted version of escape from barren, pre-orgasmic Puritanism.

Starting at about the 1:55 mark, we find one of the protagonists Nick Smith expressing his utter distaste for a certain Rick Von Sloneker whom he accuses of being a womanising heartless bastard that makes a sport out of disgracing young lasses. To wit, he narrates the tragic story of Polly Perkins. It is a cautionary tale, yet one of that is met with deep skepticism by one of the debutantes in the room.

In the next scene, Smith is confronted by Von Sloneker who casts doubt on the veracity of his account. Smith is forced to admit that Polly Perkins is really a composite of multiple individuals "like what New York magazine does". Goaded by Rick, he is forced to reveal the true identity of the person behind his tragic story. In the ensuing exchange, he is knocked down by the antagonist. In the end, Smith realizes that none of his friends are sympathetic to his side. He is branded a hypocrite and a liar with a drug problem by the hostess who storms off in disgust as Nick lays on the couch with a bleeding nose. He has no other recourse but to leave the party in disgrace.

In the following clip taken from The Last Days of Disco (1998), a discussion initiated by Kate Beckinsale's character about  post-collegiate/pre-marital life and the possibility of settling down inspired by the Disney animated movie, Lady and the Tramp, opens up a robust discussion over its plot line. Josh deconstructs the myth behind the narrative which is

essentially a primer on love and marriage directed at very young people, imprinting on their little psyches the idea that smooth-talking delinquents recently escaped from the local pound are a good match for nice girls from sheltered homes.

As he tries to make this point, Des, the character portrayed by Chris Eigeman who in Metropolitan performed the role of Nick Smith seeks to undermine his argument by first dismantling its whole premise that people don't change (his character identifies more with the tramp), and then by attacking the person of Josh insinuating that his friend has "a certain condition" and needs to take his medication to regain some lucidity. Again, here it appears the man who reifies the Victorian standards of chivalrous behavior is put down and portrayed as being out of touch and out of his mind.

Finally, in Barcelona (1994), Chris Eigeman's character corrects the naïveté of his cousin played by Taylor Nichols whose fortunes reflect that of the typical "nice guy". Referencing the 1967 film The Graduate, he cautions his usually reserved kin who is about to get married not to take anything for granted as his bride-to-be's ex-boyfriend enters the scene. In the process he discusses why marriage vows don't matter for women in the presence of the dark mysterious male.

This constant theme, as I have mentioned in the introduction to this piece, is maintained in the final installment of Stillman's "solid quartet". So why does he seem so hung up on this topic? Well for one, The director generally regards himself as a "failed writer". By that he means novelist. Perhaps he is channeling his frustrations through his films as successful authors are stereotyped as being dark and brooding profligates, while he sees himself as having missed the mark. So it may be that Stillman through his characters wonders why they often not only end up with the girl but the book deal as well.

Another clue is contained in that memorable exchange between Tom Townsend and Audrey Rouget, the main protagonists of Metropolitan. In what I regarded as the funniest line in the film when I first saw it, Tom explains to Audrey why he doesn't read novels, only "good literary criticism" because with fiction he keeps forgetting that "none of it ever happened: that it's all just made up by the author". Incidentally, this was also descriptive of my reading habits back in the 90s, which is why I self-deprecatingly laughed at it so much.

So here we find that Stillman's beef is really with writers who depict the "bad boy" as someone who often ends up with the heroine's love and affection over and above the courteous and considerate one. The problem with this has to do with the human psyche and how it operates around narratives, how we identify with protagonists and habitually act on these socially constructed identities. More than that, Stillman's disagreement seems to be with modern society at large

Why do nice guys finish last is really an existential, philosophical question about the patterns of behavior in today's world where everything boils down to a stiff competition for scarce resources and sexual conquests and where individuals are characterized as being either winners or losers in this game. Stillman's appeal in favor of a kinder, gentler, more civilized protagonist is indeed a throwback to the Victorian era, an era that the modern world has made largely anachronistic.

The reason why Whit Stillman films are so appealing is this constant harking back to an earlier period. He creates a fantasy world in which young adults speak eloquently and with erudition. The sophistication with which he imbues his characters is intellectual porn for those who seek an escape from the hollow dishonesty or drab realism of the standard Hollywood or indie flick respectively. For this reason, it is worth raising a glass (a champagne glass, of course) to toast this distinguished voice in cinema. May his questioning of the established order never end!