The Settlers

In the opening scene of L.A. Story (1991), weatherman Harris K. Telemacher—played by the film’s writer, Steve Martin—rides a stationary exercise bike in the middle of Echo Park, and captures, in voice-over, an ambivalence experienced by many middle-class, middle-aged Americans in the late  ’80s and early ’90s: “I was deeply unhappy, but I didn’t know it, because I was so happy all the time.”

Martin was born in 1945, at the vanguard of the baby boom. His was the generation that spent its formative years being courted by advertisers, who wielded sufficient cultural clout to make the Beatles the Beatles, and hula-hooping a thing. Reaching adulthood in the throes of the Vietnam War, boomers swelled the ranks of the student-protest movement, bathed in the mud of Woodstock, and railed against an outdated establishment (which happened to be populated by their parents). As Ray Kinsella, Kevin Costner’s character in Field of Dreams (1989), says, “Officially my major was English, but really it was the ’60s.” Martin and Costner’s generation was convinced of the efficacy of civil disobedience and, like no generation before it, of the centrality of individualism.

The thing about young people, though, is that they grow up—and what becomes of a bunch of kids who sloganized “Don’t trust anyone over thirty”? By the 1980s, 3.4 million baby boomers found themselves surviving various stages of midlife and its particular torments: the death of one’s parents, the weight of responsibilities financial and familial, the winnowing of life’s possibilities. These sorrows bedevil mid-lifers in any decade, but the ’80s presented a unique wrinkle. The era was, after an initial slump, a boom time, and consumption was famously conspicuous—so a wide swath of boomers, both materially comfortable and professionally accomplished, watched themselves become the establishment they had once hoped to tear down. They moved to the suburbs, became Reagan Democrats, and acknowledged that the revolution had failed: government was still corrupt; American society, with its moral panics and televangelists, was enduringly uptight; and the idealism that boomers had once cherished had largely leached from their lives. They were deeply unhappy, despite being so happy all the time.

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Mass psychological unrest has a way of trickling down, to borrow the locution of the period, and in the late ’80s and early ’90s, this conflict seeped into commercial film. There arose a micro-genre of sincere but funny existentialist narratives, all featuring boomer-aged protagonists who attempted to clarify what really matters and pinpoint how one ought to live. The most interesting of these existential-crisis films—call them “raison d’être dramedies,” or RDDs for short—include...