the Whit Stillman Poll

Stillman wanted to set the film in the past, possibly in the pre-Woodstock 1960s, but the budget did not allow for a strict period film to be made. Instead, he added period details to give the film an "aura of the past", like vintage Checker Cabs, and generally excluded anything too specific to the present day.

that period ambiguity elevates the film to a classic, and also adds a surreal element that, for example, Damsels In Distress intentionally heightens

(which is also mandatory viewing)

Were there car-rental chains in the '60s?

There may be one or two vintage cabs (which I think were still on the road anyway?), but also regular, late-model taxis... nothing in the movie struck me as ambiguous in terms of time period. Also, the characters' central concerns – decline of their social status, changing social norms – seemed specific to the late '80s, and sync up well with the end of the Reagan era (recession is mentioned). But maybe people like that, to the extent they "really exist," would have had the same anxiety in the '60s. Maybe they still do today!

They're obviously a weird, cloistered sect but (IMO) it's almost more "fun" to imagine them existing like that in the '80s than it would be if Stillman had the $$$ to achieve a period setting.

There have been car rental chains for about as long as there have been cars. Hertz goes back to the 20s, at least.

idk I took the timeline seriously. If the film came out in 1990, then the film is set in the early to mid '80s. The anachronism of deb balls coincides with the Reagan era's sudden interest in silly costumed customs.

i put it (anachronisms aside) in the late 60s or so, to jibe with audrey rouget's appearance in the last days of disco. obviously the taylor nichols character in tldod and barcelona is a time traveler or djinn of some sort. this is now WSCU (whit stillman cinematic universe) canon.