Damsels in Distress is the most inventive and adult comedy involving young people to arrive in years but that doesn't mean director Whit Stillman is going to like this review.

Stillman has been in a functional state of arrested development since the start of his career that began with Metropolis (1990) a kind of Woody Allen meets Alan Rudolph tracking of well-to-do young Manhattanites.  He followed that up with essentially the same assorted group in Barcelona (1994) and then with The Last Days of Disco (1998) it appeared he was announcing the end of his reign as a cinematic purveyor of the youthful elite. 

Now there’s Damsels in Distress, a satirical comedy with a sensibility closer to Alexander Payne than Whit Stillman, about 20-somethings that's targeted to more adult crowd. So, if Stillman hasn’t yet outgrown his fondness for collegiate clique mongering then thankfully, with Damsels, he seems to have grown into it.   

In Damsels, we meet a trio of unprecedented characters of privilege whose mission is to salvage the hopes of the hopeless. Their service to the world is to date “lesser” men than themselves. They infuse the worthless with a sense of worth and inspire in the neglected a spark of hope. We might cringe at how easily they proclaim themselves ‘better’ but we can’t deny the sincerity of their cause.

It’s clear Stillman likes these women, though they tilt towards the absurd. They’re a progressive version of Michael Lehmann’s Heathers (1988) with a naive social conscious and an intellectual curiosity performing good deeds in a rush of self-righteous certainty. 

Prior to Damsels in Distress, I never quite knew where Stillman’s sympathies lay. His characters seemed lofty in speech and manner, yet strangely innocent of any kind of damning arrogance that could warrant severe criticism. If there was a nuance extant between their affectedness and sincerity it was consistently lost on me. There was always this whispering idea that even privilege must have its menace. After all, on the scale of cinema villainy, rich people come in just after faceless corporations and Nazis. 

But my problems with Stillman are very much my problems. Matters aren’t helped that his name is Whit Stillman, a name that cannot be uttered without me wondering if, in fact, he isn’t playing some annoying prep-school game by conjuring up images of Walt Whitman. Apparently not, for he has been Whit Stillman since 1952, and has experienced the world of privilege and all that goes with it — debutante balls, European vacations and Ivy League schools, making Stillman a legitimate if not sincere voice for the much maligned group of upper-crust society. That he adds to that voice in Damsels in Distress great humour and magnificent performances from his entire cast makes this film his most entertaining yet. 

Perhaps I came to Stillman’s work too early in my career to be able to appreciate his broad strokes of approval (he casts no judgment that I can tell) without any sense of irony or cynicism. It’s difficult to conjure up any empathy for the issues, concerns and hardships of the very rich. Yet in Stillman’s world (both on and off film) these youth are still just children bumbling into adulthood – albeit adulthood cultivated toward the kind of success most of us will never know.

Director: Whit Stillman
Run Time: 99 minutes
Rating: 4.5/5