Director Whit Stillman in interview

4.30pm, GMT, 19 March. I’m re-watching the final scene of one of the great films of the 1990s, The Last Days of Disco, as a bit of last minute research before I interview its director, Whit Stillman, at 9am, PST. I’m at the beautiful coda where Chloë Sevigny and Matt Keeslar, the film’s sweet, will they, won’t they couple, are on the subway, standing by a central pole, and are suddenly compelled to dance. The O’Jays' Love Train starts to swell on the soundtrack, although no one is carrying a beatbox. Soon the whole carriage is up. The credits role and everyone keeps grooving. Sevigny has never looked so happy, so beautiful. I ignore the email that pops up at the bottom right hand corner of my computer. Turns out I shouldn’t have. It’s Stillman: “Jamie, I wanted to check whether we are still on – maybe I've messed up the time but it's 30 past 9am here in Los Angeles now.”

Like a particularly poor episode of a bad sitcom, daylight savings time kicked in Stateside at the weekend and I have left my interviewee hanging. But maybe it’s some sort of cosmic karma. Whitman, after all, has left us all waiting. For thirteen years. That’s the time that has elapsed since The Last Days of Disco played in movie theatres.

Watches are synchronised and we reschedule for a few hours later. When I eventually get Stillman on a Skype linkup he’s charmingly magnanimous about the delay. “We had a very late screening last night, our first one with the public over here, and we were drinking the cinema’s concocted ‘Pink Damsel’ cocktails [a delicious sounding blend of vodka and grapefruit]. You didn’t want to speak to me two hours ago.”

His new film is Damsels in Distress, a college campus comedy about a group of do-gooding sorority sisters, including Greta Gerwig and Analeigh Tipton, who make it their mission to improve the lives of their fellow students. I start with the obvious question: why has it taken him so long to get back behind the camera? “Well, in a word, failure. I failed to set up and get going many projects,” says the 60-year-old New Yorker. “I think part of it is also getting more into screenwriter mode, completing screenplay assignments, rather than single minded filmmaker mode, where you’re set on doing a project. I sort of abdicated the responsibility for getting the films off the ground. And they didn't get off the ground; they didn’t fly themselves, so I’ve had a lot of strikeouts.”

Stillman reels off some of the ones that got away. It's an eclectic list. There’s an adaptation of Anchee Min’s Red Azalea, set during the Cultural Revolution; a daft comedy about Martians called Little Green Men; a movie set in 60s Jamaica during, intriguingly, an angel shortage. “The problem is that they were stretches,” he explains. “Some of them had dramatic elements that people did not consider me very logical for.”

On the surface Damsels looks more in the Stillman mode. Like his so-called 'yuppie trilogy' (Metropolitan (1990), Barcelona (1994) and The Last Days of Disco (1998)), it's essentially privileged prep-school types making very withering (and hilarious) remarks to one another, but there’s a distinctly less caustic, more upbeat edge. “This one is starting a new page, I think. There is some overlap, some connections to the previous films, but it’s sillier, it's more fantastical.”

Typically Stillmanesque high-brow/low-brow references (the sexual techniques of twelfth-century Cathars, the decline in the decadence of homosexuality since the days of the dandy school of authors) commingle with jokes about a frat boy who never mastered the colours and inept suicide attempts from the campus’s two-storey library – there are even a few Fred and Ginger-style dance numbers. The cold, controlled surface of his 90s work has been replaced by a giddy feeling of organised chaos. Stillman himself struggled to keep up with the film's freewheeling comic abandon. “There are so many people in the movie who are doing funny little things, and I hope people get to see the film more than just once because there are some performances that I’m just coming to appreciate now, the things the actors were doing.”

Even with this vein of broad comedy adding a spryness to Stillman’s wryness, the director confesses to being concerned that sections of the audience will still be as miffed as they were when his 90s trio were playing to half empty cinemas. “Our films push back on a lot of cultural attitudes, which means that they are not always easily accepted,” says Stillman, wistfully. This was no more evident than at last year's London Film Festival, where Damsels played to a packed audience as the festival's surprise movie. If you had been standing outside the auditorium unaware of what was showing, you might have guessed director Sandra Hebron had lost her mind and selected some stomach churning exploitation flick – The Human Centipede III, perhaps – given the number of walk-outs, not an effervescent comedy. “We had a very strange audience response – it was like the English civil war all over again.”

Stillman has acquired a thick skin to this kind of rejection, though. When he was producing his urbane social comedies in the 90s, Tarantino (and his imitators) was the button of fashion in American independent cinema, while the comedy market had been cornered by gross-out peddlers the Farrelly brothers and Mike Myers. “Everyone seemed to be going in a Tarantino direction,” Stillman tells me, when I ask if he felt adrift from his 90s filmmaking brethren, “but not that Tarantino I would feel close to, because I think he has wonderful comic dialogue – I mean sensational dialogue – but the external aspects of Tarantino, that sort of pulp aspect, the violence. For a while it seemed like we were really off on our own with not much of a fan base.”

Today’s cinema landscape is a very different one. During the thirteen years since the financial disaster of The Last Days of Disco (it’s still trying to claw back its modest eight-million dollar budget), filmmakers like Wes Anderson and Jarred Hess have emerged as successors to Stillman and have been lucky enough to do so in a time when audiences are hungry for smart comedies told from idiosyncratic point-of-views. There’s also been a digital revolution during his extended sabbatical. A whole new sub-genre, mumblecore, has been mining toe-currling laughs from the 'comedy of mannerlessness' that the 'yuppie trilogy' epitomised, and doing so on such insignificant budgets that even with the tiny distribution they receive they still turn a profit. Conditions are therefore perfect for Stillman’s long awaited comeback.

“I think one of the most exciting things about mumblecore was that it was developing a lot of territory we were interested in, but without the cinematic means,” explains Stillman, “so really Damsels is a mumblecore film, only with clearer diction.” How appropriate, then, that Stillman chose the movement’s most celebrated actor, Greta Gerwig (scene stealer in Greenberg, The House of the Devil, and every other mainstream production she's appeared in), as his chief damsel in distress. It’s a piece of casting as inspired as when he chose the aforementioned Sevigny, then an underground actor and Manhattan It girl, as his lead in The Last Days of Disco. “They are two of my favourites. They sort of approach things the same way, where it’s a bit like, I don’t know, there’s both a naturalism and a sort of a throwing up the deck of cards and seeing where they land-quality to their performances.”

Now that Terrence Malick, American cinema’s other snail’s pace director, has suddenly accelerated his production schedule (IMDb currently lists the Texan as having four films on the go, all to be released by the end of 2013), will Stillman be following suit?

“He’s my hero,” deadpans Stillman. “Terrence Malick: dare to dream, dare to win.”

Like his characters, Stillman’s delivery is so bone-dry that I have to ask if he’s being facetious?

“I’m somewhat sincere now. He used his hiatus much more productively than I did. I think he got a graduate degree and taught philosophy. I was just wasting time in Paris cafes. Fortunately I had a few afternoons at the steeplechase race track to bring some colour into my existence.”

If you’re similarly in need of some colour in your life, Stillman’s ebullient new film is definitely worth a flutter.