Whit Stillmanis a writer, director, and occasional actor. He is best known for making comedies of manners, usually revolving around the upper classes. His dialogue is witty and quick, reminiscent of thelikes of Jane Austenand Oscar Wilde. Like many directors, Stillman has a few favored actors who he works with often. In this case, those actors are Chris Eigeman (Gilmore Girls,It’s Like, You Know…), Taylor Nichols (Pen15,Boiler Room),and Chloë Sevigny(Zodiac,We Are Who We Are). These actors each star in three of Stillman’s projects, with Eigeman and Nichols both getting their first acting roles fromMetropolitan, which is also Stillman’s directorial debut.
Before directing anything himself, Stillman made some appearances in movies as an actor. He starred in two Spanish movies,SkylineandSal Gorda, in 1983 and 1984, respectively. Almost 30 years later, he returned to the front of the camera with appearances inThe Imperialists are Still Alive!,Girl Most Likely(as himself), andMemories of My Father. Stillman’s approach to filmmaking is recognizable due to his distinct writing style even with a set of movies that span a variety of period settings. So, here are all of Whit Stillman’s movies, ranked.

5Damsels in Distress (2011)
Damsels in Distressis one of Stillman’s more recent ventures. It centers around a group of women at college who attempt to teach other students how to have better taste in clothing, dialect, and men. These central women are played by Greta Gerwig, Megalyn Echikunwoke, and Carrie MacLemore, and they take Lio Tipton’s Lily under their wing. But when they go through some ill-fated romantic entanglements, they find themselves to be the ones in distress.
This is something of a love-it-or-hate-it movie that found better success among critics than general audiences. Here, Stillman’s signature dialogue can come across as off-putting rather than endearing if your personal tastes aren’t inclined with his. The poor pacing makes the movie feel much lengthier than its 100-minute run-time, and perhaps it’s the overstayed welcome that sours Stillman’s usual charm.

Related:Greta Gerwig’s Best Performances, Ranked
4Love & Friendship (2016)
Whit Stillman’sLove & Friendshipis an adaptation of Austen’s early novella,Lady Susan, although the movie’s title comes from an unrelated Austen story. The narrative follows Lady Susan as she takes refuge at a relative’s house in order to wait out scandalous rumors circulating about her in London. While there, she sets about seducing the young and eligible Reginald De Courcy and matching up her daughter with an unwanted suitor.Kate Beckinsale starsas Lady Susan alongside Xavier Samuel as De Courcy, Chloë Sevigny as her confidant, and Morfydd Clark as her daughter, Frederica.
The writing styles of Austen and Stillman are a perfect match, and he adapts this epistolary novel for the screen expertly. The plot is not what you would expect from Austen, or anyone from that time period, instead it has modern anti-hero sensibilities and its protagonist has real agency despite the restrictions of the era. The result is hilarious, back-handedly polite dialogue and an unexpected story arc that keeps you engaged.

Related:Why Autumn de Wilde’s Emma is an Exquisite Jane Austen Adaptation
3Barcelona (1994)
In Stillman’s second movie, he turns to Europe withBarcelona. This movie finds Ted living in Barcelona when he receives an unexpected visit from a cousin, Fred, whom he doesn’t get along too well with. The two men have opposite approaches to dating, with Ted having sworn off women and Fred being something of a womanizer. Stillman’s favorites, Taylor Nichols and Chris Eigeman, play Ted and Fred respectively, and after already working together on a previous Stillman project, the pair have excellent chemistry.
As always, Stillman’s dialogue is the shining star of the movie, satirizing Americans abroad with ease and humor. What’s important here is that Stillman doesn’t fall into the easy trap of making the characters he is satirizing unwatchably annoying in order to make his point. They are nuanced enough that we can at and with them at the same time.

2Metropolitan (1990)
Of all of Stillman’s movies,Metropolitanis his most novelistic. The plot follows a young, upper-class group of friends in Manhattan during debutante season. Their group is slightly shaken up when a socialist outsider joins their ranks. Once again featuring Eigeman and Nichols, along with Edward Clements as Tom the interloper and Carolyn Farina as Audrey. Despite Tom’s ideological opposition to this group of friends, he can’t help but be drawn to Eigeman’s character Nick, and Audrey. The simple setup has a surprisingly good pay-off as a result of Stillman’s trademark combination of biting humor and earnestness.
In conversation withMetrograph, he recalls declaring “I really want to be F. Scott Fitzgerald!” when interviewing for Harvard. The influences that Stillman cites of F. Scott Fitzgerald and Austen can be seen clearly here in the insularity of this group and the construction of the movie itself. Scenes are limited to a select few locations and scenarios and while this can be chalked up to the limited budget, it’s also in keeping with the movie’s representation of this sector of society.

1The Last Days of Disco (1998)
The Last Days of Discochronicles the lives of two young women in New York City who frequent their local Studio 54-esque club. These central friends are played by Beckinsale and Sevigny with Jennifer Beals and Stillman favorites Chris Eigeman and Taylor Nichols also featuring. Each of these characters is discontented, trying to seek out the missing piece of their life at the disco, be it love, sex, or drugs. Stillman’s observations on friendship here are astute and interesting with the writing also containing his funniest work.
The characters make sweeping, deadpan proclamations about the declining state of disco and the world with endearing sincerity. Talking toVanity Fair, Stillman describes the mood of this movie as “the old story of nostalgia for the present.” From the movie’s title to its atmosphere, this idea is hugely present and well captured. Stillman has a gift for conveying a strong sense of place and that is no more evident than withThe Last Days of Disco. It’s all of his best features at their maximum potential, which is what lands it the number one spot.